Library

X
feed icon rss

Your email was sent successfully. Check your inbox.

An error occurred while sending the email. Please try again.

Proceed reservation?

Export
Filter
  • Organic Chemistry  (68,935)
  • Cell & Developmental Biology  (41,698)
  • pharmacokinetics
Source
Material
Years
Keywords
  • 101
    Electronic Resource
    Electronic Resource
    Pulmonary Bioavailability of a Phosphorothioate Oligonucleotide (CGP 64128A): Comparison with Other Delivery Routes (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 583-591 
    Details
    ISSN: 1573-904X
    Keywords: administration ; antisense ; bioavailability ; gastrointestinal ; intra-peritoneal ; intra-tracheal ; ISIS 3521 ; oligonucleotide ; oral ; pharmacokinetics ; subcutaneous
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. Phosphorothioate antisense oligodeoxynucleotides are promising therapeutic candidates. When given systemically in clinical trials they are administered via slow intravenous infusion to avoid their putative plasma concentration-dependent haemodynamic side-effects. In this study, we have evaluated alternative parenteral and non-parenteral administration routes which have the potential to enhance the therapeutic and commercial potential of these agents. Methods. The delivery of CGP 64128A by intravenous, subcutaneous, intra-peritoneal, oral and intra-tracheal (pulmonary) routes was investigated in rats using radiolabelled compound and supported by more specific capillary gel electrophoretic analyses. Results. Intravenously administered CGP 64128A exhibited the rapid blood clearance and distinctive tissue distribution which are typical for phosphorothioate oligodeoxynucleotides. Subcutaneous and intra-peritoneal administration resulted in significant bioavailabilities (30.9% and 28.1% over 360 min, respectively) and reduced peak plasma levels when compared with intravenous dosing. Administration via the gastrointestinal tract gave negligible bioavailability (〈2%). Intra-tracheal administration resulted in significant but dose-dependent bioavailabilities of 3.2, 16.5 and 39.8% at 0.06, 0.6 and 6.0 mg/kg, respectively. Conclusions. Significant bioavailabilities of CGP 64128A were achieved following subcutaneous, intra-peritoneal and intra-tracheal administration. Pulmonary delivery represents a promising mode of non-parenteral dosing for antisense oligonucleotides. The dose-dependent increase in pulmonary bioavailability suggests that low doses may be retained in the lungs for local effects whereas higher doses may be suitable for the treatment of a broader spectrum of systemic diseases.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011934011690
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 102
    Electronic Resource
    Electronic Resource
    Skin Mini-Erosion Sampling Technique: Feasibility Study with Regard to Serial Glucose Measurement (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 883-888 
    Details
    ISSN: 1573-904X
    Keywords: transdermal access ; skin erosion ; transdermal ; dermal interstitial fluid ; sampling ; glucose ; monitoring ; diabetes mellitus ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To describe a dermally non-invasive serial sampling technique and to test its clinical feasibility with regard to glucose measurement. Methods. A standardized skin mini-erosion devoid of the epidermal barrier, and covered by an artificial one, was formed by a suctioning technique. Interstitial fluid (IF) was extracted serially by brief application of negative pressure, and its glucose content compared with that in capillary or venous blood samples. Results. The procedure caused no discomfort. The epidermis regenerated rapidly after experimentation. There were no complications. In non-diabetic subjects (n = 13) the mean of all IF values measured daily for 6 days was 6.2 ± 0.1 mmol/1 (±SE). The corresponding capillary blood glucose value was 5.6 ± 0.1 mmol/1, and the venous glucose value was 5.4 ± 0.1 mmol/1. The differences between IF glucose values and invasive control values remained within narrow limits throughout. The 2SD limits of agreement for the differences were 1.44 mmol/1 (IF vs. capillary blood samples) and 1.76 mmol/1 (IF vs venous samples) respectively. The OGTT curves suggested glucose kinetics to be similar in IF and in capillary blood. In diabetic subjects, the mean of IF values determined serially during one day was 15.3 ± 1.0 mmol/1 (range, 6.7−21.8 mmol/1), and the corresponding mean capillary value was 12.0 ± 0.9 mmol/1 (range, 3.3−17.2 mmol/1). The ICC for all paired photometric observations was 0.948. Conclusions. The results suggest the new sampling technique to be a feasible approach for clinical and experimental purposes. A functionally integrated sampling patch is entering the clinical testing stage.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011924631680
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 103
    Electronic Resource
    Electronic Resource
    Receptor Occupancy in Myocardium, Adrenal Cortex, and Brain by TH-142177, a Novel AT1 Receptor Antagonist in Rats, in Relation to Its Plasma Concentration and Hypotensive Effect (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 911-917 
    Details
    ISSN: 1573-904X
    Keywords: angiotensin II receptor antagonist ; TH-142177 ; rat tissues ; ex vivo receptor occupancy ; pharmacokinetics ; pharmacodynamics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To study the relationship between angiotensin II (All) receptor occupancy ex vivo in tissues plasma concentration and hypotensive effect of a novel All receptor antagonist, TH-142177 and losartan in rats. Methods. At 2, 8 and 24 hr after oral administration of TH-142177 and losartan in rats, All receptors in myocardium, adrenal cortex and cerebral cortex were determined by radioligand binding assay using [125I]Sar1,Ile8-AII. Plasma concentrations of both drugs and metabolite in rats were also measured using validated HPLC assays. Further, systolic blood pressure (SBP) in conscious renal hypertensive rats treated orally with TH-142177 and losartan were measured by using a tail cuff plethysmographic method. Results. Oral administration of TH-142177 (1.8 and 5.5 μmol/kg) and losartan (6.5 and 21.7 μmol/kg) in rats brought about dose-dependent decreases in [125I]Sar1,Ile8-AII binding sites (Bmax) in myocardium and adrenal cortex. The extent of receptor occupancy by both drugs in adrenal cortex was maximal at 2 hr later but that in myocardium at 8 hr later. Further, the receptor occupancy was more sustained in myocardium than adrenal cortex. The ex vivo binding affinity of TH-142177 for All receptors in these tissues was roughly three times higher than that of losartan. Also, cerebral cortical [125I]Sar1,Ile8-AII binding was significantly reduced by oral administration of losartan but not by TH-142177. The time course of All receptor occupancy by both drugs in adrenal cortex appeared to be in parallel with that of their plasma concentrations, while the time course in myocardium correlated with that of their hypotensive effects rather than plasma concentrations. Conclusions. TH-142177 produced a relatively selective and sustained occupancy ex vivo of All receptors in myocardium and adrenal cortex of rats with approximately three times greater potency than losartan. Its time course of myocardial receptor occupancy was in parallel with that of hypotensive effect rather than plasma concentration.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011932800729
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 104
    Electronic Resource
    Electronic Resource
    Pharmacokinetics and Biodistribution of a Nucleotide-Based Thrombin Inhibitor in Rats (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 904-910 
    Details
    ISSN: 1573-904X
    Keywords: GS522 ; oligodeoxynucleotide ; pharmacokinetics ; tritiated ; biodistribution ; rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To characterize the pharmacokinetic and tissue distribution profiles of a nucleotide-based thrombin inhibitor (GS522, phosphodiester oligonucleotide, GGTTGGTGTGGTTGG) following intravenous administration to rats. Methods. Pharmacokinetic study: 10 mg/kg, 20 mg/kg, 30 mg/kg (6 animals/dose) were administered to rats by rapid injection into the femoral vein. Blood samples were collected over a 45 minute period. Plasma concentrations of GS522 were determined using capillary gel electrophoresis with laser-induced fluorescence detection. Biodistribution Study: l0mg/kg (400μl, 31.46 μCi/ml) of 3H-GS522 was administered to rats by rapid injection into the femoral vein. The animals were sacrificed by decapitation at 1, 5, 10, 30, 60, 360 minutes post-dose (3 rats/point). Brain, blood, duodenum, eyes, heart, kidney, liver, lungs, muscle, pancreas, skin, spleen and vein samples were collected, processed and quantitated using liquid scintillation counting. Results. The pharmacokinetic profile declines in multiexponential manner, exhibiting extremely fast distribution and elimination (t1/2 = 7.6−9.0 min, Cl = 22.0−28.0 ml/min, V = 83.9−132.4 ml/kg). GS522 follows linear pharmacokinetics, with the area under the curve being proportional to the dose (Rsq = 0.9744). Highest radioactivity levels were detected in kidney, liver and blood (39.7, 15.7 and 15.3% dose/ respective organ). Less than 1% of the dose was detected in the heart, spleen and lungs, and 〉0.3% of the dose was found in the brain and eyes. The oligonucleotide associated radioactivity was uniformly distributed between the brain regions (left and right lobe and cerebellum). Six hours following the dose administration a statistically significant increase (p 〈 0.05) in radioactivity levels was observed in the brain, eyes, skin, liver, pancreas and vein. Conclusions. The pharmacokinetic and biodistribution profiles of GS522 following intravenous administration to rats at three doses were characterized. The oligonucleotide associated radioactivity was widely distributed in tissues. The amount of radioactivity sharply decreased with time in most tissues. Kidney, liver and muscle were the main sites of accumulation. The oligonucleotide associated radioactivity did not cross the blood brain barrier to an appreciable extent. In addition, a statistically significant increase (p 〈 0.05) in the radioactivity levels observed in select tissues suggested a re-uptake mechanism for intact oligonucleotide or its degradation products.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011980716659
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 105
    Electronic Resource
    Electronic Resource
    Guar Gum-Based Sustained Release Diltiazem (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 1196-1201 
    Details
    ISSN: 1573-904X
    Keywords: guar gum ; sustained release ; extended release ; diltiazem ; dissolution ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. This study was performed to examine the use of guar gum to sustain the release of diltiazem under in vitro and in vivo conditions. Methods. Guar gum tablet formulations were prepared and evaluated under a variety of in vitro dissolution conditions. The formulations, along with Dilacor XR®, were administered to a group of eight fasted, healthy volunteers in a four period crossover study. Results. Varying the lot of guar gum as well as using guar from different suppliers had little effect on diltiazem dissolution. Also, dissolution of diltiazem from guar gum tablets was essentially independent of stir speed under normal conditions (USP Apparatus II). The stability of guar-based formulations under stressed conditions (40°C/75% relative humidity for 3 months) was also established. All four formulations gave similar plasma concentrations over time in the healthy volunteers pharmacokinetic study. Conclusions. Guar gum-based matrix tablets represent a simple and economical alternative to existing diltiazem sustained release dosage forms.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011931622536
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 106
    Electronic Resource
    Electronic Resource
    Risedronate Gastrointestinal Absorption Is Independent of Site and Rate of Administration (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 228-232 
    Details
    ISSN: 1573-904X
    Keywords: risedronate ; gastrointestinal absorption ; gastrointestinal site ; bisphosphonate ; administration rate ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. Two studies were conducted to compare the absorption of risedronate administered as a solution to three different gastrointestinal sites (study A) and to determine the extent of absorption of risedronate solution administered by rapid and slow infusion to the second part of the duodenum (study B). Methods. Each study was designed as a single-dose, crossover (three periods, study A; two periods, study B) trial in healthy male subjects, with a 14-day washout period between dosing. Subjects fasted overnight before drug administration and for 4 hours after drug administration. In study A, a risedronate solution of 40 mg in 30 mL of water was administered directly into the stomach, the second part of the duodenum, or the terminal ileum over 1 minute via a nasoenteral tube in a three-period crossover design. In study B, a risedronate solution of 40 mg in 30 mL of water was administered directly into the second part of the duodenum over 1 minute and over 1 hour in a randomized, two-period crossover design. Serum and urine samples were obtained for 48 hours after dosing for risedronate analysis. Results. Eight subjects completed each study. No statistically significant site-specific differences in any pharmacokinetic parameter were observed (study A). Based on the area under the serum concentration-time profile and the amount of drug excreted in the urine unchanged, the extent of risedronate absorption did not differ significantly following a rapid or a slow infusion (study B). Only minor symptomatic complaints were reported by subjects, such as headaches and body aches. Conclusions. These studies indicate that the rate and extent of risedronate absorption are independent of the site of administration along the gastrointestinal tract, and that the extent of absorption is not affected by the rate of administration.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011910517200
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 107
    Electronic Resource
    Electronic Resource
    Influence of Different Fat Emulsion-Based Intravenous Formulations on the Pharmacokinetics and Pharmacodynamics of Propofol (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 442-448 
    Details
    ISSN: 1573-904X
    Keywords: propofol ; pharmacokinetics ; pharmacodynamics ; rats ; EEG ; fat emulsion
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. The influence of different intravenous formulations on the pharmacokinetics and pharmacodynamics of propofol was investigated using the effect on the EEG (11.5-30 Hz) as pharmacodynamic endpoint. Methods. Propofol was administered as an intravenous bolus infusion (30 mg/kg in 5 min) or as a continuous infusion (150 mg/kg in 5 hours) in chronically instrumented male rats. Propofol was formulated as a 1% emulsion in an Intralipid 10%®-like fat emulsion (Diprivan-10®, D) or as a 1%- or 6% emulsion in Lipofundin® MCT/LCT-10% (Pl% and P6%, respectively). EEG was recorded continuously and arterial blood samples were collected serially for the determination of propofol concentrations using HPLC. Results. Following bolus infusion, the pharmacokinetics of the various propofol emulsions could adequately be described by a two-compart-mental pharmacokinetic model. The average values for clearance (Cl), volume of distribution at steady-state (Vd,ss) and terminal half-life (t1/2, λ2) were 107 ± 4 ml/min/kg, 1.38 ± 0.06 l/kg and 16 ± 1 min, respectively (mean ± S.E., n = 22). No significant differences were observed between the three propofol formulations. After continuous infusion these values were 112 ± 11 ml/min/kg, 5.19 ± 0.41 l/kg and 45 ± 3 min, respectively (mean±S.E., n = 20) with again no statistically significant differences between the three propofol formulations. Comparison between the bolus- and the continuous infusion revealed a statistically significant difference for both Vd,ss and t1/2, λ2 (p 〈 0.05), whereas Cl remained unchanged. In all treatment groups infusion of propofol resulted in a burst-suppression type of EEG. A profound hysteresis loop was observed between blood concentrations and EEG effect for all formulations. The hysteresis was minimized by a semi-parametric method and resulted in a biphasic concentration-effect relationship of propofol that was described non-parametrically. For P6% a larger rate constant onset of drug effect (t,1/2, keo) was observed compared to the other propofol formulations (p〈0.05). Conclusions. The pharmacokinetics and pharmacodynamics of propofol are not affected by to a large extent the type of emulsion nor by the concentration of propofol in the intravenous formulation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011980432646
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 108
    Electronic Resource
    Electronic Resource
    Effect of GF120918, a Potent P-glycoprotein Inhibitor, on Morphine Pharmacokinetics and Pharmacodynamics in the Rat (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 599-605 
    Details
    ISSN: 1573-904X
    Keywords: morphine ; morphine-3-glucuronide ; P-glycoprotein ; pharmacokinetics ; pharmacodynamics ; antinociception ; central nervous system ; analgesia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. The objective of this study was to evaluate the effect of a potent P-gp inhibitor, GF120918, on the systemic pharmacokinetics and antinociceptive pharmacodynamics of a single intravenous dose of morphine in rats. Methods. Male Sprague-Dawley rats received either 500 mg base/kg/d GF120918 or vehicle for 4 days by gavage, or no pretreatment. On day 4, morphine was administered as a 1- or 2-mg/kg i.v. bolus. Antinociception, expressed as percent of maximum possible response (%MPR), was evaluated over 300 min after morphine administration. Serial blood samples were collected and analyzed for morphine and morphine-3-glucuronide (M3G) by HPLC. Results. Morphine clearance and distribution volume were not altered significantly by GF120918. M3G AUC in the GF120918-treated rats was approximately 2-fold higher than in vehicle-treated rats. For both morphine doses, %MPR and the area under the effect-time curve at 300 min were significantly higher in the GF120918-treated rats. A pharmacokinetic/pharmacodynamic effect model accurately described the effect-concentration data for the rats that received 1-mg/kg morphine; ke0 was significantly smaller for GF 120918- vs. vehicle-treated and control rats (0.060 ± 0.028 vs. 0.228 ± 0.101 vs. 0.274 ± 0.026 min−1, p=0.0023). EC50 and γ were similar between treatment groups. Conclusions. Pretreatment with GF 120918 enhanced morphine antinociception, as assessed by the hot-lamp tail-flick assay, and elevated systemic M3G concentrations in rats. The differential pharmacologic response to morphine in the GF120918-treated animals could not be attributed to alterations in systemic morphine pharmacokinetics.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011938112599
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 109
    Electronic Resource
    Electronic Resource
    Effect of Particle Size and Charge on the Disposition of Lipid Carriers After Intratumoral Injection into Tissue-isolated Tumors (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 128-132 
    Details
    ISSN: 1573-904X
    Keywords: pharmacokinetics ; tissue-isolated tumor ; liposome ; emulsion ; intratumoral injection
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. Pharmacokinetic properties of various lipid carriers (liposome and emulsions) after intratumoral injection were studied in perfusion experiments using tissue-isolated tumor preparations of Walker 256 carcinosarcoma. Methods. Four types of lipid carriers, large emulsion (254 nm), small emulsion (85 nm), neutral liposomes (120 nm) and cationic liposomes (125 nm) were prepared. We quantified their recovery from the tumor, leakage from the tumor surface and venous outflow after intratumoral injection into perfused tissue-isolated tumors, and analyzed venous appearance curves based on a pharmacokinetic model. Results. In contrast to the small emulsion and neutral liposomes, which immediately appeared in the venous outflow perfusate following intratumoral injection, the appearance of the cationic liposomes and the large emulsion was highly restricted, clearly demonstrating that intratumoral clearance of these formulations can be greatly retarded by the cationic charge and large particle size, respectively. The venous appearance rate-time profiles were fitted to equations derived from a two-compartment model by nonlinear regression analysis. When the calculated parameters were compared among these four formulations, the venous appearance rate did not exhibit such a large difference; however, the rate of transfer from the injected site to the compartment which involves clearance by venous outflow was all very different. Conclusions. The results of this study indicate that the determining factor which alters the pharmacokinetic properties of these lipid carriers after intratumoral injection is not the rate of transfer from the interstitial space to the vascular side but the rate of intratumoral transfer from the injection site to the well-vascularized region.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011921324952
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 110
    Electronic Resource
    Electronic Resource
    Lack of In Vivo/In Vitro Correlations for 50 mg and 250 mg Primidone Tablets (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 1085-1089 
    Details
    ISSN: 1573-904X
    Keywords: primidone ; bioavailability ; human ; pharmacokinetics ; in vitro dissolution
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To determine if large differences in the in vitro dissolution profiles for primidone tablets would result in significant bioavailability differences. Methods. Two separate bioavailability studies were conducted. The first study used 18 healthy subjects and compared the bioavailability of an old 50 mg tablet formulation, a new 50 mg tablet formulation, and a suspension containing 50 mg/ml of primidone. The second study enrolled 24 subjects who were to receive a new 250 mg tablet formulation, two lots of an old 250 mg tablet formulation and a 250 mg tablet from a second manufacturer. In vitro dissolution was conducted over 90 minutes, using USP 23 Apparatus 2 at 50 rpm, with 900 ml of water. Results. Dissolution at 90 minutes for the old and new 50 mg tablets was approximately 20% and 100%, respectively. The dissolution of the four 250 mg tablets ranged from approximately 30% to 100%. The 50 mg tablet that dissolved slower had a longer Tmax and a 14% lower Cmax than the more rapidly dissolving tablet, but the AUC(0−∞) values differed by only 3%. Only nine subjects completed the 250 mg study because of side effects. The differences in Cmax and AUC(0−∞) among the four 250 mg tablets were less than 7%. Conclusions. Even though there were large differences in the in vitro dissolution of the 50 mg and the 250 mg primidone tablets, the two 50 mg tablets were shown to be bioequivalent, as were the four 250 mg tablets.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011942530288
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 111
    Electronic Resource
    Electronic Resource
    Estimation of Oral Bioavailability of a Long Half-Life Drug in Healthy Subjects (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 1782-1786 
    Details
    ISSN: 1573-904X
    Keywords: bioavailability ; pharmacokinetics ; squalene synthase inhibitor ; prodrug
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To estimate and compare the oral bioavailability of a drug (BMS-187745) administered as single doses of oral solution of either the parent drug or its prodrug (BMS-188494). Methods. A single-dose, two-period, three-treatment, control-balanced, residual-effect, incomplete block crossover study was completed in 16 healthy male subjects. All subjects received a 10 mg IV infusion of BMS-187745, and a single oral dose of either BMS-187745 (PO1) or BMS-188494 (PO2). A model is proposed to calculate the oral bioavailability of BMS-187745 which has a long half-life; incomplete data points were available to characterize its elimination phase. The plasma concentration-time data obtained following IV infusion of parent drug, and after administration of either PO1 or PO2 treatment were fitted simultaneously with systemic pharmacokinetic parameters shared by both the oral and IV routes of administration. Results. The best simultaneous fittings of the plasma concentration-time data were obtained by using a biexponential pharmacokinetic model with a first-order absorption rate constant. The mean bioavailability (F) values of BMS-187745 estimated by the proposed model were 26.5% and 2.6% when given as oral solution of its prodrug and as the parent drug. The coefficient of variation (CV) of these F values are reasonable, ranging from 38−40%. In contrast, F calculated by the model-independent AUC method exhibited high CV, ranging from 111−120%. Conclusions. The oral bioavailability values estimated by the proposed model were more reasonable compared to those calculated by the model-independent AUC method. The proposed approach may be useful for estimating bioavailability of long half-life drugs when incomplete data points are available to characterize their elimination phase.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011977116543
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 112
    Electronic Resource
    Electronic Resource
    Combined Use of Carboxyl-Directed Protein Pegylation and Vector-Mediated Blood-Brain Barrier Drug Delivery System Optimizes Brain Uptake of Brain-Derived Neurotrophic Factor Following Intravenous Administration (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 576-582 
    Details
    ISSN: 1573-904X
    Keywords: pegylation ; blood-brain barrier ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. Peptide drug delivery to the brain requires optimization of (a) plasma pharmacokinetics and (b) blood-brain barrier (BBB) permeability. In the present studies, plasma pharmacokinetics are improved with protein pegylation and BBB transport is facilitated with the use of vector-mediated drug delivery using the OX26 monoclonal antibody (MAb) to the rat transferrin receptor, which undergoes receptor-mediated transcytosis through the BBB in vivo. Methods. A conjugate of OX26 and streptavidin (SA), designated OX26/SA, was prepared in parallel with the carboxyl-directed pegylation of brain-derived neurotrophic factor (BDNF). A novel bifunctional polyethyleneglycol (PEG) was used in which a hydrazide (Hz) was attached at one end and a biotin moiety was attached to the other end. This allowed for conjugation of BDNF-PEG-biotin to OX26/SA. Results. The brain uptake of BDNF-PEG-biotin was increased following conjugation to OX26/SA to a level of 0.144 ± 0.004% injected dose per g brain and a BBB permeability-surface area product of 2.0 ± 0.2 μL/min/g. Conclusions. These studies demonstrate that peptide drug delivery to the brain can be achieved with advanced formulation of protein-based therapeutics. The formulation is intended to (a) minimize rapid systemic clearance of the peptide, and (b) allow for vector-mediated drug delivery through the BBB in vivo. Following this dual formulation, the brain uptake of a neurotrophin such as BDNF achieves a value that is approximately 2-fold greater than that of morphine, a neuroactive small molecule.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011981927620
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 113
    Electronic Resource
    Electronic Resource
    Pharmacokinetics of antipyrine in rats with different resistance to hypoxia in cold stress (1998)
    Springer
    Bulletin of experimental biology and medicine 126 (1998), S. 1098-1099 
    Details
    ISSN: 1573-8221
    Keywords: pharmacokinetics ; antipyrine ; individual resistance to hypoxia ; cold stress
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract It is shown that the parameters of antipyrine pharmacokinetics during cold exposure depend on individual resistance to hypoxia. High-resistant rats are characterized by less intense metabolism and more rapid normalization of pharmacokinetic parameters than lowresistant rats characterized by shortened elimination half-time corresponding to a more rapid metabolism of xenobiotics under conditions of cold stress.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02447243
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 114
    Electronic Resource
    Electronic Resource
    The effect of feed quality on the kinetic disposition of orally administered triclabendazole in sheep (1998)
    Springer
    Veterinary research communications 22 (1998), S. 257-263 
    Details
    ISSN: 1573-7446
    Keywords: anthelmintics ; Fasciola ; nutrition ; pharmacokinetics ; sheep ; triclabendazole
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The effect of two qualities of feed on the kinetic disposition of triclabendazole (TCBZ) metabolites was investigated in sheep (n = 4) following oral administration of TCBZ at 10 mg/kg body weight. The same sheep were given sequentially two qualitatively different diets: a low-quality (LQ) diet based on wheat straw ad libitum, and a high-quality (HQ) diet based on barley+alfalfa. The triclabendazole sulphoxide (TCBZSO) and triclabendazole sulphone (TCBZSO2) concentrations were determined in blood samples taken serially from the jugular vein between 5 min and 9 days after TCBZ administration. The parent drug TCBZ was not detected in any of the samples. The quality of feed affected the kinetics of both TCBZ metabolites. The rate of appearance (Tlag and Tmax) in the jugular blood was slower and the formed amount (AUC) of TCBZSO was slightly higher when the sheep were on the LQ diet (Tlag = 7.74 h; Tmax = 27.91 h; AUC = 1042 μg.h/ml) than when they were offered the HQ diet (Tlag = 1.90 h; Tmax = 16.01 h; AUC = 832.4 μg.h/ml). The MRT of TCBZSO was about 40% longer with the LQ diet than with the HQ diet. Similarly, the rate of appearance of TCBZSO2 in plasma of sheep was slower when they were on the LQ diet than when they were on the HQ diet, suggesting an impairment of the hepatic enzymatic activity involved in the oxidation of TCBZSO to TCBZSO2.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006095400309
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 115
    Electronic Resource
    Electronic Resource
    Some Pharmacokinetic Parameters and Dosage Regimens for a Long-Acting Formulation of Oxytetracycline in 6- to 8-Month-Old Male Calves (1998)
    Springer
    Veterinary research communications 22 (1998), S. 533-544 
    Details
    ISSN: 1573-7446
    Keywords: calves ; dosage regimen ; oxytetracycline ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract A two-way crossover study was conducted in crossbred male calves (6–8 months old) to determine the bioavailability, pharmacokinetics and dosage regimens for a long-acting formulation of oxytetracycline (OTC-LA). The half-lives of oxytetracycline after intravenous and intramuscular administration were 7.8 h and 24 h, respectively. The volume of distribution and total body clearance values of the drug were 0.86±0.07 L and 76.1±3.3 (ml/h)/kg, respectively. The maximum concentration of the drug in the serum (4.7–7.4 μg/ml) was achieved 8–10 h after intramuscular administration. The minimum therapeutic serum concentration of drug of ≥0.5 μg/ml was maintained between 15 min and 84 h after intramuscular administration. The intramuscular bioavailability of the drug was 89.1±4.2%. The dosage regimens to maintain the minimum therapeutic serum concentrations of OTC following intramuscular administration of OTC-LA were computed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006193703979
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 116
    Electronic Resource
    Electronic Resource
    The Pharmacokinetics and Efficacy of Long-Term Low-Level and Split-Dose Administration of Albendazole Through In-Feed Formulations against Ovine and Caprine Parasitic Gastroenteritis (1998)
    Springer
    Veterinary research communications 22 (1998), S. 467-477 
    Details
    ISSN: 1573-7446
    Keywords: albendazole ; anthelmintic ; goat ; in-feed ; metabolite ; pharmacokinetics ; sheep
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Two trials were conducted against natural and experimentally induced parasitic gastroenteritis in sheep and goats using an in-feed formulation of albendazole to evaluate its therapeutic and prophylactic efficacy. In the first trial, albendazole was incorporated in feed pellets to deliver an average daily dose of 0.7 mg/kg body weight in order to evaluate its prophylactic efficacy. In the second trial, feed pellets were offered to deliver an average total dose of 8.0 mg/kg body weight in two equal split doses in order to evaluate its curative efficacy. Sustained plasma concentrations of the active compound, albendazole sulphoxide, and its metabolite albendazole sulphone, sufficient to prevent establishment of infection, were achieved when the animals were allowed to feed on medicated pellets for 10 consecutive days. The bioavailability of the metabolites of albendazole following the administration of a therapeutic dose in two split doses of the in-feed formulation was sufficient to remove established adult nematodes. The concentrate feed pellets could be used for self-medicating small ruminants for therapeutic use as well as for prophylaxis based on their strategic use appropriate to the epidemiology of the parasitic disease.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006127132161
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 117
    Electronic Resource
    Electronic Resource
    Plasma, Urinary and Biliary Residues in Cattle Following Intramuscular Injection of Nortestosterone Laurate (1998)
    Springer
    Veterinary research communications 22 (1998), S. 479-491 
    Details
    ISSN: 1573-7446
    Keywords: cattle ; nortestosterone ; pharmacokinetics ; residues
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The synthetic androgen 19-nortestosterone (β-NT) has been used illegally as a growth promoter in cattle production in the European Union. Elimination of β-NT and its metabolites in plasma, urine and bile was studied in three cattle with cannulated gallbladders following intramuscular injection at a single site of 500 mg of the laurate ester (NTL) containing 300.5 mg β-NT. Using enzyme immunoassay quantification, plasma Cmax of free β-NT was 0.5±0.15 μg/L (mean±SEM). Concentrations of free β-NT in plasma were consistently greater than the assay limit of quantification (0.12 μg/L) for 32.7±13.42 days. Mean residence time for free β-NT in plasma was 68.5±20.75 days. Following sample preparation by immunoaffinity chromatography, high-resolution GC-MS was used to quantify β-NT and α-NT in urine and bile. β-NT was detected irregularly in urine from two of the three animals post injection. The principal metabolite present in the urine, α-NT, was detected for 160.3±22.67 days post injection. Cmax for α-NT in urine was 13.7±5.14 μg/L. Mean urinary AUC0–183 days for α-NT was 845.7±400.90 (μg h)/L. In bile, α-NT was the only metabolite detected for 174.3±8.67 days post treatment. Cmax for α-NT in bile was 40.8±12.70 μg/L and mean biliary AUC0–183 days for α-NT was 1982.6±373.81 (μg h)/L. Concentrations of α-NT in bile samples were greater than those in urine samples taken at the same time. The mean ratio of biliary:urinary AUC0–183 days was 3.0±0.72. It is concluded that bile is a superior fluid for detection of α-NT following injection of NTL, owing to the longer period during which residues may be detected after administration.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006179116231
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 118
    Electronic Resource
    Electronic Resource
    Comparative Disposition Kinetics of Albendazole in Sheep Following Oral and Intraruminal Administration (1998)
    Springer
    Veterinary research communications 22 (1998), S. 545-551 
    Details
    ISSN: 1573-7446
    Keywords: albendazole ; metabolites ; pharmacokinetics ; route of administration ; sheep
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The pharmacokinetics of albendazole was studied in sheep following single oral and intraruminal administration at nematocidal dose rates. The disposition curves of its metabolites indicated increased uptake of the drug in sheep following intraruminal as compared to oral dosing (p〈0.05). The increased bioavailability of benzimidazole anthelmintics given by the intraruminal route could be exploited for optimizing the use of anthelmintic for sustained parasite control in small ruminants.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006145820818
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 119
    Electronic Resource
    Electronic Resource
    Nephrologic complications of drug therapy in the elderly (1998)
    Springer
    Geriatric nephrology and urology 8 (1998), S. 29-44 
    Details
    ISSN: 1573-7306
    Keywords: aged ; contrast sensitivity ; drug toxicity ; hyperkalemia ; pharmacokinetics ; renal failure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1008203008239
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 120
    Electronic Resource
    Electronic Resource
    Immediate and Long-Term Effects of 5,7-Dihydroxytryptamine on Rat Striatal Serotonergic Neurons Measured Using In Vivo Voltammetry (1998)
    Springer
    Neurochemical research 23 (1998), S. 1-6 
    Details
    ISSN: 1573-6903
    Keywords: 5,7-Dihydroxytryptamine ; intracerebroventricular administration ; serotonin release ; in vivo voltammetry ; pharmacokinetics ; striatum
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The immediate and long-term effects of the selective serotonergic neurotoxin 5,7-dihydroxytryp-tamine (5,7-DHT) on rat striatal serotonergic neurons were examined after its intracerebroventricular administration using in vivo voltammetry. Extracellular concentration of 5-hydroxyindoles increased immediately following intracerebroventricular 5,7-DHT injection (200 μg in 24 μl, 18 min), peaked at 1.5-2 h, and returned to normal by 4 h. 5,7-DHT diffused to the contralateral striatum in detectable amounts 9 to 12 min after the start of injection and returned to basal levels by 1.5 h. Three to 6 days after 5,7-DHT lesions, 5-hydroxytryptophan administration produced an increase in striatal 5-hydroxyindoles that was greater than that produced in pre-lesioned rats. This effect was maximal at 14 to 17 days post-lesion, and remained even after 50 days. The short-term effect of 5,7-DHT may be attributable to increased serotonin release, inhibition of uptake, or monoamine oxidase inhibition. The long-term effect of 5,7-DHT lesions may attributable to increased synthesis of serotonin or decreased reuptake in remaining serotonergic neurons.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1022460216822
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 121
    Electronic Resource
    Electronic Resource
    Elucidation of Human Amphotericin B Pharmacokinetics: Identification of a New Potential Factor Affecting Interspecies Pharmacokinetic Scaling (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 1630-1636 
    Details
    ISSN: 1573-904X
    Keywords: amphotericin B ; pharmacokinetics ; human ; gender-differences ; disposition function differences ; interspecies scaling
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To elucidate the pharmacokinetics of amphotericin B in rats, mice and humans, and to perform interspecies scaling to humans using allometry. Methods. Plasma concentrations following intravenous bolus administration in rats, and mice were determined by HPLC. Human pharmacokinetic parameters elucidated from literature data were validated in a preliminary study involving a patient receiving daily infusion dose for 27 days. A critical literature review was conducted to identify appropriate pharmacokinetic parameter values in other species for interspecies scale-up. Interspecies allometric scale-up was performed across mice, rats, rabbits and dogs and the resulting predictions in humans were compared to observed values. Results. A triexponential decline in rat, mouse and human plasma concentrations were observed. No gender differences in rat pharmacokinetics were observed. In contrast to allometry, mouse CL was smaller (82 vs 116 ml/h/kg) and T0.5 (33 vs 20 h) was longer compared to rat. In the preliminary human study, Cpeak and Cmin values remained relatively constant over the duration of therapy, and a CL, MRT, T0.5, Vss and Vdarea of 26 ml/h/kg, 10 and 23 days, 6.2 and 20 L/kg, respectively, were estimated. The relative contributions of the terminal phase area in rat, mouse and human were 75%, 92% and 31%, respectively. Interspecies allometric scale-up predictions of human CL (41 ml/h/kg), CLu (467 ml/h/kg) and Vss (3.3 L/kg) were similar to reported values, whereas poor predictions of human Vuss (33 L/kg), Vdarea (4.1 L/kg) and T0.5 (3 days) were obtained. Conclusions. Insignificant accumulation in humans inspite of the long terminal T0.5 was rationalized to be due to the small terminal-phase area contribution. While human CL and Vss were sucessfully predicted in the interspecies scaling, poor predictions of human Vdarea and T0.5 were obtained, which was attributed to disposition pattern differences between humans and other species, a potential new critical factor affecting interspecies scale-up.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011923704731
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 122
    Electronic Resource
    Electronic Resource
    Pharmacokinetics and Leukocyte Responses of Recombinant Human Interleukin-10 (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 1895-1901 
    Details
    ISSN: 1573-904X
    Keywords: IL-10 ; cytokines ; protein ; immunosuppression ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To study the pharmacokinetics and ex vivo leukocyte responses of recombinant human IL-10 (rHuIL-10) following single SC and IV dosing. Methods. A randomized two-way cross-over study was undertaken in 17 healthy volunteers in which rHuIL-10 was administered as 25 μg/ kg SC and IV doses. Blood samples were collected for 48 hr after dosing to determine serum IL-10 concentrations. Inhibitory activity of IL-10 on ex vivo production of inflammatory cytokines (TNF-α and IL-1β) by LPS-treated peripheral blood cells were measured over 96 hr. Results. A physiologically-relevant modeling approach was developed to determine the pharmacokinetics for two routes of administration (SC and IV). The IV dose showed polyexponential disposition with CL of 65 mL/kg/hr, Vss of 70 mL/kg, and t1/2 of 1.94 hr. Absolute bioavailability averaged 42% for SC dosing which produced lower but sustained concentrations. Substantial and prolonged suppression of TNF-α and IL-1β production was achieved during IL-10 treatment. The Hill Function was used to account for the joint concentration-dependent immunosuppressive action of rHuIL-10 after both IV and SC doses. The IC50 values were about 0.03 ng/mL and Imax values were about 0.85 for both TNF-α and IL-lβ suppression. The degree of change as well as the duration of leukocyte response was greater after SC administration than after IV administration. Conclusions. rHuIL-10 shows favorable PK/PD characteristics especially by theSC route of administration which produced prolonged suppression of cytokine production (ex vivo) which may be applicable in various immune-related disorders.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011918425629
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 123
    Electronic Resource
    Electronic Resource
    Use of the Stable Isotopes Technique to Evaluate the Bioavailability of a Pharmaceutical Form of Magnesium in Man (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 347-351 
    Details
    ISSN: 1573-904X
    Keywords: magnesium ; absolute bioavailability ; stable isotopes ; pharmacokinetics ; ICP-MS
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011947525377
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 124
    Electronic Resource
    Electronic Resource
    Correction for Non-Ideal Tracer Pharmacokinetic Disposition by Disposition Decomposition Analysis (DDA) (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 1469-1473 
    Details
    ISSN: 1573-904X
    Keywords: drug tracer ; labeling ; pharmacokinetics ; erythropoietin ; iodination
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. Pharmacokinetic (PK) studies assume that the tracer's PK is equivalent to the parent compound. This assumption is often violated. The aim of this work is to present a method enabling the ideal tracer PK, i.e. the PK of the parent compound, to be predicted from the non-ideal tracer. Methods. The procedure uses a disposition decomposition-recomposition (DDR) that assumes that the labeling mainly changes the elimination kinetics while the distribution kinetics is not significantly affected. In the DDR procedure an elimination rate constant correction factor (kCOR) is determined from a simultaneously fitting to plasma concentration data resulting from an i.v. injection of both the tracer and the parent compound. The correction factor is subsequently used to predict the ideal tracer PK behavior from the disposition function (i.v. bolus response) of the non ideal tracer. Results. The DDR method when applied to plasma level data of erythropoietin (r-HuEPO) and its iodinated tracer (l25I-r-HuEPO) from a high (4000U/kg) and a low (400U/kg) dosing of r-HuEPO in newborn lambs (n = 13) resulted in excellent agreements in the elimination rate corrected dispositions in all cases (r = 0.995, SD = 0.0095). The correction factor did not show a dose dependence (p 〉 0.05). The correction factors were all larger than 1 (kCOR = 1.94, SD = 0.519) consistent with a reduction in the EPO elimination by the iodination labeling. Conclusions. The DDR tracer correction methodology produces a better differentiation of the PK of endogenously produced compounds by correcting for the non-ideal PK behavior of chemically produced tracers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011922209757
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 125
    Electronic Resource
    Electronic Resource
    Correlation of Plasma Clearance of 54 Extensively Metabolized Drugs Between Humans and Rats: Mean Allometric Coefficient of 0.66 (1998)
    Springer
    Pharmaceutical research 15 (1998), S. 1474-1479 
    Details
    ISSN: 1573-904X
    Keywords: plasma clearance ; unbound plasma clearance ; inter-species scale-up in plasma clearance ; allometric analysis ; pharmacokinetics ; rat vs. human
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Purpose. To evaluate the distribution of allometric exponents for relationship of total plasma clearance of 54 extensively metabolized drugs, with wide-ranging linear clearance values, between humans and rats, to provide a rationale for the observed data, and to discuss potential significance of the findings. Methods. Human and rat plasma clearance values of 54 drugs with markedly different physicochemical properties were obtained from the literature. Standard allometric analysis was performed for each drug using both rat and human data. Unbound vs. total plasma clearances were obtained for 15 out of 54 drugs and their correlations between humans and rats were compared. Results. The mean ± SD of the allometric exponent for the 54 drugs studied is 0.660 ± 0.190. The median clearance ratio based on unit body weight is 7.41 and the median exponent is 0.645. Excluding two outliers the correlation coefficient of plasma clearance between humans and rats was 0.745 (p 〈 0.0001). For the 15 drugs, use of unbound plasma clearance approach seems to significantly improve the correlation coefficient compared to total plasma clearance (0.940 vs. 0.841). Conclusions. The present study indicates that on average, humans and rats may eliminate extensively metabolized drugs at a rate similar to that expected from the allometric or body surface area relationship of basal metabolic rate between the two species. A simple statistical distribution hypothesis is used to rationalize the species difference in plasma drug clearance. Rat may serve as an useful animal model to predict (unbound) plasma clearance of drugs in humans.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1011974226596
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 126
    Electronic Resource
    Electronic Resource
    The disposition kinetics of albendazole following the administration of single and divided doses to cattle and buffalo (1998)
    Springer
    Veterinary research communications 22 (1998), S. 87-96 
    Details
    ISSN: 1573-7446
    Keywords: anthelmintic ; albendazole ; buffalo ; cattle ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Concentrations of albendazole sulphoxide and its sulphone metabolite in plasma in cattle and buffalo were measured by high-performance liquid chromatography after single and divided intraruminal administration of albendazole at the recommended nematocidal and fasciolicidal dose rates of 7.5 and 15.0 mg/kg body weight, respectively. No significant differences in the plasma concentrations of the metabolites or their pharmacokinetic parameters were observed between cattle or buffalo at either dose rate. Pharmacokinetic analysis and the disposition curve of the metabolites indicated increased uptake of the drug in both cattle and buffalo when the same total amount of the drug was given in divided doses compared to a single dose (p〈0.05). The divided dose schedules of administration could possibly be exploited to extend the life of the available benzimidazole anthelmintics.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006023328617
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 127
    Electronic Resource
    Electronic Resource
    A preliminary study of the pharmacokinetics of fenoprofen enantiomers following intravenous administration of the racemate to cats (1998)
    Springer
    Veterinary research communications 22 (1998), S. 203-208 
    Details
    ISSN: 1573-7446
    Keywords: anti-inflammatory ; cat ; enantiomer ; fenoprofen ; NSAID ; pharmacokinetics ; racemic ; stereoselectivity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006077406388
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 128
    Electronic Resource
    Electronic Resource
    Preliminary observations on the pharmacokinetics of CDRI compound 81/470 in calves (1998)
    Springer
    Veterinary research communications 22 (1998), S. 67-72 
    Details
    ISSN: 1573-7446
    Keywords: anthelmintic ; benzimidazole ; calf ; pharmacokinetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1005939328885
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 129
    Electronic Resource
    Electronic Resource
    Molecular imprinting technology: challenges and prospects for the future (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 195-209 
    Details
    ISSN: 0899-0042
    Keywords: molecular imprinting ; molecular recognition ; chirality ; chromatography ; catalysis ; biosensor ; immunoassay ; antibody mimic ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Molecular imprinting is a technique for the fabrication of biomimetic polymeric recognition sites or “plastic antibodies/receptors” which is attracting rapidly increasing interest. By this technology, recognition matrices can be prepared which possess high substrate selectivity and specificity. In the development of this technology, several applications have been foreseen in which imprinted materials may be exchanged for natural recognition elements. Thus, molecularly imprinted polymers have been used as antibody/receptor binding mimics in immunoassay-type analyses, as enzyme mimics in catalytic applications and as recognition matrices in biosensors. The best developed application area for imprinted materials, though, has been as stationary phases for chromatography, in general, and chiral chromatography, in particular. This review seeks to highlight some of the more intriguing advantages of the technique as well as pointing out some of the difficulties encountered. The prospects for future development will also be considered. Chirality 10:195-209, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 130
    Electronic Resource
    Electronic Resource
    Separation of (R)- and (S)-tert-butyl 2-tert-butyl-4-methoxy-2,5-dihydro-1,3-imidazole-1-carboxylate (building block for amino acid synthesis) by preparative high performance liquid chromatography on a polysaccharide stationary phase (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 217-222 
    Details
    ISSN: 0899-0042
    Keywords: amylose ; 3,5-dimethylphenyl-carbamate ; polysaccharide phase ; tert-butyl 2-tert-butyl-4-methoxy-2,5-dihydro-1,3-imidazole-1-carboxylate; amino acid ester synthesis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The preparative separation of the enantiomers of the title compound, a versatile chiral building block for the synthesis of unnatural amino acid esters, by high performance liquid chromatography on a chiral stationary phase (CSP), is reported for the first time. The CSP consists of amylose-(3,5-dimethylphenyl-carbamate), which has been coated onto the surface of macroporous aminopropyl-functionalized silica gel. The effect of mobile phase composition and the amount of amylose derivative on the silica gel has been thoroughly investigated. Using 2-propanol as organic modifier in hexane as mobile phase, on a semi-preparative column (200 mm × 40 mm ID, containing 192 g of stationary phase) about 200 mg of the racemate was separated per injection. Running the equipment under automatic conditions with repetitive injection mode allowed for the separation of 30 g per day. Both enantiomers were obtained with enantiopurities 〉99.75:0.25. Chirality 10:217-222, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 131
    Electronic Resource
    Electronic Resource
    Species-dependent enantioselective pharmacokinetics of PNU-103017, a Pyrone HIV protease inhibitor (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 210-216 
    Details
    ISSN: 0899-0042
    Keywords: enantiospecific assay ; rat ; dog ; human ; enantiomer disposition ; HIV protease inhibitor ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: PNU-103017, 4-Cyano-N-(3-(cyclopropyl(5,6,7,8,9,10-hexahydro-4-hydroxy-2-oxo-2H-cycloocta(b) pyran-3-yl)methyl)phenyl)-benzenesulfonamide, is a selective HIV aspartyl protease inhibitor under evaluation as a potential oral treatment of Acquired Immunodeficiency Diseases. PNU-103017 is a racemic mixture of two enantiomers, designated PNU-103264 (R-) and PNU-103265 (S-). Stereoselective pharmacokinetics of the two enantiomers of PNU-103017 were observed in the dog, rat, and human after single and multiple dose administration of the racemate and were apparently species-dependent. Mean enantiomeric ratios of plasma concentrations (R-/S-) at each time point were greater than 1 in the dog, ranging from 1.22 to 3.06, but less than 1 in the rat and in the human, ranging from 0.44 to 0.80 and 0.23 to 0.73, respectively. A trend towards increased or decreased (farther from 1:1, R-/S-) enantiomeric ratio of plasma concentrations with time after each administration was also observed. The enantiomeric ratio remained unchanged after multiple dose administration in the rat, dog, and human although enzyme induction and increased plasma clearance were observed for both enantiomers. Chirality 10:210-216, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 132
    Electronic Resource
    Electronic Resource
    Chiral interaction and stochastic kinetics in stirred crystallization of amino acids (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 238-245 
    Details
    ISSN: 0899-0042
    Keywords: chiral selectivity ; amino acid crystallization ; molecular recognition ; stochastic kinetics ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A study of chirally selective interaction in the stirred crystallization of glutamic acid and lysine is presented. The crystallization of S-glutamic acid is influenced by the presence of S-lysine but not R-lysine. Crystal nuclei in stirred systems are produced due to secondary nucleation. Secondary nucleation is an autocatalytic process in which a crystal produces secondary nuclei due to fluid motion, and due to crystal stirrer and crystal-crystal collisions. As a result of this autocatalysis, small fluctuations in the nucleation rates are amplified and the kinetics show a marked stochastic behavior. We investigate the stochastic behavior in detail and propose a kinetic mechanism that explains both the increase and the statistical distribution of the crystallization times of S-glutamic acid due to the presence of S-Lysine. Chirality 10:238-245, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 133
    Electronic Resource
    Electronic Resource
    Enantiomers of thalidomide: blood distribution and the influence of serum albumin on chiral inversion and hydrolysis (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 223-228 
    Details
    ISSN: 0899-0042
    Keywords: thalidomide enantiomers ; in vitro kinetics ; blood distribution ; human serum albumin ; chiral inversion ; plasma protein binding ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The aim of this investigation was to elucidate the distribution and reactions of the enantiomers of thalidomide at their main site of biotransformation in vivo, i.e., in human blood. Plasma protein binding, erythrocyte: plasma distribution, and the kinetics of chiral inversion and degradation in buffer, plasma, and solutions of human serum albumin (HSA) were studied by means of a stereospecific HPLC assay. The enantiomers of thalidomide were not extensively bound to blood or plasma components. The geometric mean plasma protein binding was 55% and 66%, respectively, for (+)-(R)- and (-)-(S)-thalidomide. The corresponding geometric mean blood:plasma concentration ratios were 0.86 and 0.95 (at a haematocrit of 0.37) and erythrocyte:plasma distributions were 0.58 and 0.87. The rates of inversion and hydrolysis of the enantiomers increased with pH over the range 7.0-7.5. HSA, and to a lesser extent human plasma, catalysed the chiral inversion, but not the degradation, of (+)-(R)- and (-)-(S)-thalidomide. The addition of capric acid or preincubation of HSA with acetylsalicylic acid or physostigmine impaired the catalysis to varying extents. Correction for distribution in blood enhances previously observed differences between the pharmacokinetics of the enantiomers in vivo. The findings also support the notion that chiral inversion in vivo takes place mainly in the circulation and in albumin-rich extravascular spaces while hydrolysis occurs more uniformly in the body. In addition, the chiral inversion and hydrolysis of thalidomide apparently occur by several different mechanisms. Chirality 10:223-228, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 134
    Electronic Resource
    Electronic Resource
    Mechanistic aspects of the biogenesis of rose oxide in Pelargonium graveolens L'Héritier (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 229-237 
    Details
    ISSN: 0899-0042
    Keywords: deuterium labelling ; menthocitronellol ; citronellol ; enantioselective multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS) ; dynamic headspace analysis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mechanistic aspects of the biogenesis of the chiral monoterpenoid rose oxide in Pelargonium graveolens L'Héritier are investigated using deuterium-labelled precursors. After administration of the precursors using the cut-stem method, the dynamic headspace extracts of the plants are analysed using multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS). It is unequivocally shown that this plant is able to convert citronellol and menthocitronellol into cis-/trans-rose oxide. Menthocitronellol is converted into rose oxide with a clearly detectable enantiodiscrimination. These facts may be explained with the presence of an oxidase, which is able to oxidize citronellol and menthocitronellol in allylic position. A photooxygenation mechanism including singlet oxygen as the oxidizing agent is rather unlikely. Chirality 10:229-237, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 135
    Electronic Resource
    Electronic Resource
    Chloroperoxidase-induced asymmetric sulfoxidation of some conformationally restricted sulfides (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 246-252 
    Details
    ISSN: 0899-0042
    Keywords: sulfoxides ; chloroperoxidase ; asymmetric oxidation ; enantioselective ; episulfide ; gas chromatography ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Asymmetric sulfoxidation by means of a chloroperoxidase from Caldariomyces fumago and hydrogen peroxide as the oxygen source was studied for a series of sterically well-defined substrates. The stereochemistry of the sulfoxidation was the same for all substrates studied. While 2,3-dihydrobenzo[b]thiophene (1) is an excellent substrate (giving 99.5% yield and 99% e.e. of the (R)-sulfoxide), replacement of a methylene group by either a more sterically demanding group or a heteroatom caused a substantial decrease in reactivity or in reactivity as well as enantioselectivity. A further investigation of the lowered catalytic efficiency of chloroperoxidase with these substrates has been carried out in a series of competitive reactions. Thus, benzo[1,3]oxathiole (5) acted as a competitive inhibitor of the enzyme, whereas 1-thiochroman (2) and 1-thiochroman-4-one (3) were shown to be too sterically demanding to significantly compete for the active site. For the oxidation of 2, 3, and 5, it was found that in the low CPO concentration range the chemical yield after 60 min reaction time increased almost linearly with the amount of CPO used. The products from 2 and 3 could be obtained in over 80% yield with an e.e. exceeding 96%. Chloroperoxidase was also found to be an effective catalyst in the oxidation of labile episulfides, yielding the corresponding anti-sulfoxides quantitatively and giving 12% e.e. of (1R, 2R)-sulfoxide in the oxidation of propylene sulfide. Chirality 10:246-252, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 136
    Electronic Resource
    Electronic Resource
    1997 Chirality Medal (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 281-281 
    Details
    ISSN: 0899-0042
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No abstract.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 137
    Electronic Resource
    Electronic Resource
    Circular dichroism of axially chiral methaqualone, 3-Aryl-2-mercapto- and 3-aryl-2-alkylthio-4(3H)-quinazolinones: conformational dependence of CD and assignment of absolute configuration (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 253-261 
    Details
    ISSN: 0899-0042
    Keywords: chiroptical properties ; Cotton effect ; atropisomerism ; quantum-mechanical calculation ; AM1 ; CNDO/S ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Rotational strengths calculated on the basis of quantum-mechanically obtained minimum energy geometries were used to determine the absolute configurations of axially chiral 3-aryl-4(3H)-quinazolinones from the sign of the observed Cotton effects (CEs). For the spectral data, CNDO/S calculations were used; for the geometries, ab initio (RHF/6-31G) and semiempirical (AM1) theories were used. Oscillator and rotational strengths of all excited states down to 200 nm were compared to experimental absorption and circular dichroism (CD) data. It was found that the sign of the 1Lb Cotton effects obtained for the enantiomers of methaqualone and derivatives of 3-aryl-2-alkylthio-4(3H)-quinazolinones can be correlated unambiguously with the absolute configuration. Furthermore, the sign of the Cotton effect of the π-π* transition of the thiocarbonyl chromophore of 3-aryl-2-mercapto-4(3H)-quinazolinones is suitable for a successful stereochemical correlation. Chirality 10:253-261, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 138
    Electronic Resource
    Electronic Resource
    Sympathomimetic enantiomers and asthma (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 262-272 
    Details
    ISSN: 0899-0042
    Keywords: airway ; beta2-agonist ; racemic ; eutomer ; distomer ; hyperreactivity ; bronchospasm ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Airways of asthma patients can become hyperresponsive to airway spasmogens following regular use of isoprenaline or β2-selective sympathomimetics. Hyperreactivity that results from acute exposure of animals to these drugs is pre-empted by vagal section (a procedure which does not influence spasmolytic efficacy of sympathomimetics), is not diminished by antagonism of β2-adrenoceptors and is not associated with loss of responsivity of β2-adrenoceptors in the airways. Since activation, modulation, or blockade of β2-adrenoceptors does not determine this form of hyperreactivity, the possibility that distomers may induce hyperreactivity must be considered. Ocular and vascular responses to distomers of sympathomimetics have long been recognised and, more recently, comparable observations have been made for the airways. Thus, reactivity of guinea-pig airways to spasmogens was increased following exposure to S-isoprenaline, S-salbutamol, or S-terbutaline and exposure to S-isoprenaline or S-salbutamol can intensify symptoms in asthmatics. Regular exposure to the racemate, especially during or following an allergic reaction, predisposes to expression of hyperreactivity, which is nullified, acutely, by the eutomer. These observations imply that biological effects of sympathomimetic distomers may contribute to morbidity and mortality in asthma patients. Chirality 10:262-272, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 139
    Electronic Resource
    Electronic Resource
    Immobilized vancomycin as chiral stationary phase in packed capillary liquid chromatography (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 273-280 
    Details
    ISSN: 0899-0042
    Keywords: direct chiral separation ; mobile phase composition ; NSAIDs ; retention model ; vancomycin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Fused silica-packed capillary columns containing vancomycin immobilized by reductive amination on an aldehyde-silica were used to separate enantiomers of some non-steroidal anti-inflammatory drugs. Attempts have been made to qualitatively explain the influence of various mobile phase compositions on the enantioselective retention. The effects of mobile phase pH, buffer, and organic modifier concentrations were investigated as well as the influence of salts of hydrophobic ions added to the mobile phase to induce ion pair retention. Chirality 10:273-280, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 140
    Electronic Resource
    Electronic Resource
    Carbamates of cellulose bonded on silica gel: Chiral discrimination ability as HPLC chiral stationary phases (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 283-288 
    Details
    ISSN: 0899-0042
    Keywords: chiral HPLC ; cellulose carbamates ; enantiomeric resolution ; warfarin ; flurbiprofen ; lorazepam ; oxazepam ; pindolol ; tertatolol ; nicardipine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Four cellulose mixed 10-undecenoate/carbamate derivatives, simultaneously bearing 10-undecenoyl and variously substituted phenylaminocarbonyl groups, were chemically bonded on allylsilica gel. The study of the effect of these substitutions on the performance of the resulting chiral supports, and a comparison with the recently described 10-undecenoate/3,5-dimethylphenylcarbamate derivative, are presented. In this study heptane/2-propanol or heptane/chloroform mixtures were used as mobile phases. Chirality 10:283-288, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 141
    Electronic Resource
    Electronic Resource
    Correlation between time reversal symmetry and chirality in certain molecular processes (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 289-293 
    Details
    ISSN: 0899-0042
    Keywords: chirality ; time reversal symmetry ; asymmetric synthesis ; enantiomerism ; isomerism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: If a molecule is identified not only by its static spatial constructions, but also by the motions at the sub-molecular level, application of time reversal symmetry operation to a certain molecule could lead to another distinguishable from the original in the sense of sub-molecular motions, a phenomenon now defined as time reversal isomerism. Assessment of the consideration of certain enantiomers as distinguishable time reversal isomers is suggested in order to evoke a comprehensive interpretation of a likely correlation between the two types of isomerisms. The conceptual basis of a connection between absolute asymmetric synthesis under the influence of external fields and the intrinsic time reversal symmetry violation at the molecular level is also established to encourage new experimental investigations on this theme. Chirality 10:289-293, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 142
    Electronic Resource
    Electronic Resource
    Synthesis of regioselectively substituted cellulose derivatives and applications in chiral chromatography (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 294-306 
    Details
    ISSN: 0899-0042
    Keywords: cellulose ; regioselective derivatization ; chiral stationary phases ; liquid chromatography ; enantioseparation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Various cellulose-2,3-bis-arylcarbamate-6-O-arylesters and cellulose-2,3-bis-arylester-6-O-arylcarbamates, designed to test the possible combined effects of the known tris-arylcarbamate and tris-arylester classes, were synthesized with high regioselectivity at O-C(6), and their use as CSPs in liquid chromatography for enantiomeric separations was investigated. The separations obtained with the synthesized CSPs were compared to the separations achieved on a self-packed reference column, consisting of cellulose-tris-(3,5-dimethylphenyl-carbamate) as CSP standard. Among the synthesized, regioselectively substituted cellulose derivatives, 2,3-bis-O-(3,5-dimethylphenylcarbamate)-6-O-benzoate-cellulose and 2,3-bis-O-(benzoate)-6-O-(3,5-dichlorophenylcarbamate)-cellulose gave the best CSPs for the separation of the test racemates. CSPs from regioselectively substituted cellulose derivatives seem to exhibit higher selectivities than cellulose-tris-(3,5-dimethylphenylcarbamate) for certain classes of racemic compounds. Chirality 10:294-306, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 143
    Electronic Resource
    Electronic Resource
    Enantiomeric separation of rac-indoprofen by a biocatalytic procedure (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 321-324 
    Details
    ISSN: 0899-0042
    Keywords: NSAID ; esterification ; resolution ; Candida antarctica lipase ; rac-Indoprofen ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Lipase from Candida antarctica, commercially available immobilised on acrylic resin as Novozym® 435, allows for enantioselective esterification of rac-indoprofen (±)-1, with methanol in a dioxane-toluene solvent system. A double esterification process affords methyl ester (-)-(R)-2 in 85% e.e. and enantiopure (+)-(S)-1, both in good chemical yield. Chirality 10:321-324, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 144
    Electronic Resource
    Electronic Resource
    Kinetics of racemization of (+)- and (-)-diethylpropion: Studies in aqueous solution, with and without the addition of cyclodextrins, in organic solvents and in human plasma (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 307-315 
    Details
    ISSN: 0899-0042
    Keywords: configurational stability ; pH ; temperature ; ionic strength ; phosphate buffer concentration ; plasma protein affinity ; native cyclodextrins ; cyclodextrin derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The configurational stability of (+)- and (-)-diethylpropion [(+)- and (-)-2-(diethyl)-1-phenyl-1-propanone or (+)- and (-)-DEP] was investigated systematically from chemical, pharmaceutical, and pharmacological aspects. The enantiomeric ratio was monitored directly with a recently developed stability-indicating enantioselective HPLC method.In aqueous solutions, the rate of racemization increased non-linearly with increasing pH and with increasing phosphate buffer concentration. The racemization rate showed a positive slope with increasing temperature and decreasing ionic strength.The racemization rates of (+)- and (-)-DEP in the presence of cyclodextrins (CDs) did not differ significantly. CDs that were added to (+)- and (-)-DEP in a molar ratio 5:1 showed the following effects after dissolution in 10 mM phosphate buffer (final pH 6.7): sulfobutyl ether-β-CD (SBE-β-CD) and methylated-β-CD (Me-β-CD) retarded racemization; whereas hydroxypropyl-β-CD (HP-β-CD), acetyl-γ-CD (Ac-γ-CD), acetyl-β-CD (Ac-β-CD), γ-CD, and β-CD showed a weak destabilising effect. In contrast to the described CDs, α-CD distinctly accelerated the rate of racemization.The configurational stability of (+)- and (-)-DEP was also studied under physiological conditions. The half-life of racemization in heparinised human plasma was for both enantiomers determined to be approximately 23-25 min.In phosphate buffer (10 mM, pH 7.4), rac-DEP showed a high, but unselective affinity towards human α1-acid glycoprotein (orosomucoid) immobilised on silica (Chiral AGP).The rate of racemization of the free base of (-)-DEP dissolved in organic solutions generally increases with the polarity of the solvating agent. Chirality 10:307-315, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 145
    Electronic Resource
    Electronic Resource
    Determination of the rotational barriers of atropisomeric polychlorinated biphenyls (PCBs) by a novel stopped-flow multidimensional gas chromatographic technique (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 316-320 
    Details
    ISSN: 0899-0042
    Keywords: atropisomeric polychlorinated biphenyls (PCBs) ; Chirasil-Dex ; rotational barrier ; stopped-flow multidimensional gas chromatographic technique ; on-line enantiomerization kinetics ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The rotational barriers ΔG
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 146
    Electronic Resource
    Electronic Resource
    Discrimination in resolving systems. III: Pseudoephedrine-mandelic acid (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 325-337 
    Details
    ISSN: 0899-0042
    Keywords: diastereomeric salts ; molecular recognition ; hydrogen bonding ; thermal analysis ; crystallography ; solubility ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (+)-(1S;2S)-Pseudoephedrine and racemic mandelic acid form three distinct diastereomeric salts from solutions in 95% ethanol. The least-soluble phase, a hemihydrate, contains the (2R)-mandelate. A salt phase of intermediate solubility is the unsolvated double salt, containing both the (2R)- and the (2S)-mandelate. The most-soluble salt phase contains the (2S)-mandelate. Mandelate configuration and order of solubility (based on the heats of fusion) is inverted from that found in the same system synthesized from chiral base and acid, and then crystallized from benzene solution. The (2R)-mandelate hemihydrate (-H2O at 349.5K, mp 391K), monoclinic, P21, a = 6.788(5), b = 29.415(35), c = 9.488(10)Å, β = 108.91(8)°, Z = 4 (2 ion-pairs/asymmetric unit). Intermediate double salt (2S)- and (2R)-mandelate, mp 377.6K, anorthic, P1, a = 7.758(4), b = 9.966(5), c = 13.366(6)Å, α = 72.99(4), β = 79.98(4), γ = 70.51(4)°, Z = 1 (2 ion-pairs/asymmetric unit). The (2S)-mandelate (mp 386.2K), orthorhombic, P212121, a = 7.079(6), b = 13.443(10), c = 18.820(14)Å, Z = 4 is identical to a salt made from a combination of enantiomeric moieties from benzene solution. While differing from ephedrine mandelates in configuration at one center, solubilities of pseudoephedrine mandelates in 95% ethanol are much larger. A comparison of molecular structure (non-polar and H-bonding) regions of pseudoephedrine and ephedrine mandelates shows similarities and differences that are tentatively linked to crystal properties. This study reemphasizes the necessity for consistency in solvent use in resolution and in phase identification and comparison because the phases produced are frequently dependent upon the solvent. Chirality 10:325-337, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 147
    Electronic Resource
    Electronic Resource
    Manipulation of chiral resolution for isoxazoline-based IIb/IIIa receptor antagonists using various mobile phase additives in subcritical fluid chromatography (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 338-342 
    Details
    ISSN: 0899-0042
    Keywords: additive ; selectivity ; efficiency ; modifier ; subcritical fluid chromatography ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Subcritical fluid chromatography (SubFC) using a carbon dioxide-methanol mobile phase is used for the chiral resolution of IIb/IIIa receptor antagonist enantiomers. The chiral resolution of three analogs, each containing two chiral centers, is optimized using various mobile phase additives. The effects that acidic, basic, and neutral additives have on retention, efficiency, and resolution are examined. The additive that gives the best resolution was found to be dependent upon the functionality and charge of the chiral analyte. For charged analytes, additives that act as competing ions of the same charge as the chiral analyte dramatically improve efficiency and resolution. Resolution of neutral chiral analyte enantiomers is also greatly affected by the choice of mobile phase additive. Chirality 10:338-342, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 148
    Electronic Resource
    Electronic Resource
    Mechanism of chiral asymmetry generation by chiral autocatalysis in the preparation of chiral octahedral cobalt complex (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 343-348 
    Details
    ISSN: 0899-0042
    Keywords: chiral asymmetry generation ; chiral autocatalysis ; primary nucleation ; secondary nucleation ; chiral cobalt complex ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral asymmetry generation, the predominant production of one enantiomer in a non-chiral environment, could occur in the production of the chiral complex cis-[CoBr(NH3)(en)2]Br2 by the reaction of [Co(H2O)2{(OH)2Co(en)2}2](SO4)2 with ammonium bromide in an aqueous medium. The main kinetic steps in the reaction system have been determined. During the reaction, the product crystallizes at an early stage. When a very small amount of crystalline enantiomer was added to the reaction system at an early stage, the same enantiomer was produced preferentially; in addition, the enantiomeric excess of the product increased with increasing the stirring rate. Thus, it seems that each enantiomer generates chiral crystals that could self-replicate through secondary nucleation when the solution is stirred; these crystals in turn enhance the production of the same enantiomer. With a computer code that simulates such a kinetic mechanism, it is shown that enantiomeric excess observed in the experiments could be reproduced. Chirality 10:343-348, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 149
    Electronic Resource
    Electronic Resource
    Stereoselective renal secretion of carbenicillin in rabbits: Role of the organic anion transporter at the renal brush border membrane (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 349-357 
    Details
    ISSN: 0899-0042
    Keywords: carbenicillin ; stereoselective ; secretion ; transport ; rabbit ; membrane vesicles ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Stereoselectivity in the renal secretion of carbenicillin (CBPC) was studied in rabbits. Significant renal secretion of CBPC was observed in vivo, with the secretion of the S-epimer being greater than that of the R-epimer. Stereoselective transport of CBPC was further studied in vitro using basolateral and brush border membrane vesicles prepared from rabbit kidneys. The transport of CBPC by the organic anion transporter into the basolateral membrane vesicles (BLMV) was not stereoselective. In contrast, a distinct stereoselectivity was observed in the transport of CBPC by the organic anion transporter into the brush border membrane vesicles (BBMV), with the transport of the S-epimer being more favorable. Significant epimer-epimer interactions were also observed in the transport into BBMV. The stereoselectivity of the transport of CBPC was calculated from the kinetic parameters with consideration of epimer-epimer interactions and was similar to that observed in vivo. It was concluded that the observed stereoselectivity in the renal secretion of CBPC in vivo reflected that of transport via the organic anion transporter located at the brush border membrane. Chirality 10:349-357, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 150
    Electronic Resource
    Electronic Resource
    Emanuel Gil-Av honorary issue of Chirality (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 371-372 
    Details
    ISSN: 0899-0042
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No abstract.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 151
    Electronic Resource
    Electronic Resource
    Determination of the enantiomeric purity of commercial Jacobsen's catalyst samples (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 362-363 
    Details
    ISSN: 0899-0042
    Keywords: Jacobsen's catalyst ; enantiomeric purity determination ; chiral HPLC ; cyclodextrin chiral stationary phases ; enantioseparation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A HPLC method is described for the chiral analysis of the commercially available Jacobsen's catalyst. A hydroxypropyl β-cyclodextrin stationary phase was used in conjunction with a nonaqueous, polar-organic mobile phase. The method can be applied to control the enantiomeric purity of the catalyst, which is of great importance for quality control of that product. High accuracy in the determination of trace levels of the unwanted enantiomer in the presence of large amounts of the desired enantiomer is demonstrated. Chirality 10:362-363, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 152
    Electronic Resource
    Electronic Resource
    Enantiomeric separation of several cyclic imides on a macrocyclic antibiotic (vancomycin) chiral stationary phase under normal and reversed phase conditions (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 358-361 
    Details
    ISSN: 0899-0042
    Keywords: cyclic imides ; barbiturates ; piperidine-2,6-diones ; mephenytoin ; chiral recognition ; enantioselectivity ; vancomycin chiral stationary phase ; normal-phase mode ; reversed-phase mode ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Several cyclic imidic compounds (barbiturates, piperidine-2,6-diones, and mephenytoin) are enantiomerically resolved via high-performance liquid chromatography (HPLC) on a macrocyclic antibiotic covalently bonded to a silica gel support. The Chirobiotic V chiral stationary phase (CSP) column contains the antibiotic vancomycin as the chiral selector. The results of the analysis show that the substituents at the chiral carbon position of the racemic drugs affect chiral resolution. In addition, ring size may also play a role when considering the formation of analyte-CSP inclusion complexes. Contrary to the piperidine-2,6-diones, the chromatographic parameters for the barbiturates are much the same under normal- or reversed-phase conditions. The details of these results are discussed. Chirality 10:358-361, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 153
    Electronic Resource
    Electronic Resource
    Emanuel Gil-Av (1916-1996): A man with a legacy (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 373-374 
    Details
    ISSN: 0899-0042
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No abstract.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 154
    Electronic Resource
    Electronic Resource
    Separation of nicotine and nornicotine enantiomers via normal phase HPLC on derivatized cellulose chiral stationary phases (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 364-369 
    Details
    ISSN: 0899-0042
    Keywords: (±)nicotine ; (±)nornicotine ; chiral separation ; enantiomers ; normal phase HPLC ; mobile phase additive ; cellulose-based chiral stationary phase ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: This paper describes the enantiorecognition of (±)nicotine and (±)nornicotine by high-performance liquid chromatography using two derivatized cellulose chiral stationary phases (CSPs) operated in the normal phase mode. It was found that different substituents linked to the cellulose backbone significantly influence the chiral selectivity of the derivatized CSP. The results showed that, in general, the tris(4-methylbenzoyl) cellulose CSP (Chiralcel OJ) surpasses tris(3,5-dimethylphenyl carbamoyl) cellulose CSP (Chiralcel OD). On the former column, the resolution (±)nicotine and (±)nornicotine enantiomers depended largely on mobile phase compositions. For the separation of the nicotine enantiomers, the addition of trifluoroacetic acid to a 95:5 hexane/alcohol mobile phase greatly improved the enantioresolution, probably due to enhanced hydrogen bonding interactions between the protonated analytes and the CSP. For (±)nornicotine separation, a reduction in the concentration of alcohol in the mobile phase was more effective than the addition of trifluoroacetic acid. Possible solute-mobile phase-stationary phase interactions are discussed to explain how different additives in the mobile phase and different substituents on the cellulose glucose units of the CSPs affect the separation of both pairs of enantiomers. Chirality 10:364-369, 1998. Published 1998 Wiley-Liss, Inc.This article is a US Government work and, as such, is in the public domain in the United States of America.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 155
    Electronic Resource
    Electronic Resource
    Chiral separation of enantiomers via selector/selectand hydrogen bondings (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 382-395 
    Details
    ISSN: 0899-0042
    Keywords: selector/selectand associates ; hydrogen bonding ; chiral separation ; chiral phases ; enantioselectivity ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The progress made in the development of chiral stationary phases based on hydrogen-bonding selector/selectand associates is reviewed here. The structure of the different selectand/selector systems was established through X-ray diffraction and other spectroscopic techniques. The structure of the energetically more stable diastereomeric-associate was then correlated to the chromatographic results, namely to the elution order and the enantioselectivity of each of the systems. Chirality 10:382-395, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 156
    Electronic Resource
    Electronic Resource
    A closer study of chiral retention mechanisms (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 375-381 
    Details
    ISSN: 0899-0042
    Keywords: retention mechanisms ; separation of enantiomers ; chiral stationary phases ; equilibrium isotherms ; bonding ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The retention mechanisms and the separation of enantiomers on the classes of chiral stationary phases which are made by bonding isolated groups on the surface of an adsorbent are discussed. It is shown that retention on these phases originates from mixed mechanisms and how the individual contributions of these two mechanisms can be separated, by determining and modeling the equilibrium isotherms. A contribution originating from interactions of the isomers with the nonselective sites (type-I) and another one due to interactions with the enantioselective sites (type-II) can be determined and their importance studied as a function of several parameters, e.g., temperature or pH. This approach is illustrated with results obtained with different pairs of enantiomers on bovine serum albumin, 4-methylcellulose tribenzoate, or cellobiohydrolase immobilized on silica. Chirality 10:375-381, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 157
    Electronic Resource
    Electronic Resource
    Tripodal trispeptide selector as a model for establishing the importance of hydrogen-bonding in enantiomer-separation (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 396-404 
    Details
    ISSN: 0899-0042
    Keywords: chirality ; helicity ; GC-stationary phase ; conformations ; 1H-NMR-studies ; molecular mechanics calculations ; enantiomer separation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The manner of hydrogen-bonding to peptide selectors in enantiomer separation is examined with the help of a structural model. This model relies on a C3-symmetric trispeptide selector, which is stabilized by a network of distinct intramolecular hydrogen bonds. A combination of experimental and theoretical tools enables us to identify the lowest-energy conformation of the trispeptide selector and the sites of selector-substrate interactions. Experimental tools include temperature dependent 1H-NMR studies, 1D-NOE-measurements, and titration experiments, with the theoretical tools being EFF and CFF91 molecular mechanics calculations. The structural information deduced from these investigations is shown to bear on the enantioseparation of the corresponding chiral stationary phase towards derivatized amino acids. These observations, taken together, help to rationalize the mode of enantiomer-separation by amide phases as involving predominantly C7-hydrogen bonding sites. Chirality 10:396-404, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 158
    Electronic Resource
    Electronic Resource
    The chiral code: From DNA primary structures to quaternary assemblies (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 405-414 
    Details
    ISSN: 0899-0042
    Keywords: chiral-discrimination ; homochirality ; stereospecificity ; self-assembly ; supercoiling ; cholesteric mesophase ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Nucleic acids are characterized by a predominant right-handed helical configuration that derives from the chirality of the sugar moiety. Hitherto, only “local” effects of this helical asymmetry, exemplified by DNA interactions with small compounds, have been documented. The results described in this study indicate that an enhanced asymmetry is required for the manifestation of chiral effects in DNA self-assembly processes or for chiral discrimination upon interactions with peptides. Two cases in which the intrinsic DNA asymmetry is enhanced are reported: rod-like superhelical species derived from linear DNA molecules, and topologically constrained supercoiled DNA. In the first case, the superhelical grooves within the DNA rods allow for a stereospecific complexation with peptides, resulting in chiral discrimination. In the second case, it is shown that the properties of cholesteric assemblies derived from supercoiled DNA are strictly determined by the enhanced asymmetry associated with molecular supercoiling. The results allow for new reflections on the concept of molecular complementarity, and indicate that spontaneously obtained chiral DNA mesophases might have played a key role in determining terrestrial homochirality. Chirality 10:405-414, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 159
    Electronic Resource
    Electronic Resource
    Aspects of spontaneous separation of enantiomers in two- and three-dimensional crystals (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 415-424 
    Details
    ISSN: 0899-0042
    Keywords: chiral separation ; two- and three-dimensional crystals ; grazing incidence X-ray diffraction ; atomic force microscopy ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Spontaneous separation of enantiomers in two- and three-dimensional crystals is driven by the same thermodynamic and kinetic factors. However, amphiphilic crystalline monolayers at an interface cannot possess a center of inversion, the most common symmetry element in bulk crystals. This fact should, in principle, lead to better chances for spontaneous separation in the Langmuir or Langmuir-Blodgett monomolecular films. On the other hand, the monolayers of most amphiphiles studied to date incorporate long aliphatic chains that have an intrinsic tendency to pack in a herring-bone motif requiring glide plane symmetry, thus creating a bias towards racemate formation. Moreover, 2-D crystals supposedly have a much higher degree of molecular and therefore enantiomeric disorder compared to bulk crystals. All these factors necessitate a careful choice of molecules to guarantee enantiomeric separation in two dimensions. Unambiguous detection of spontaneous resolution in 2-D appears to require atomic resolution of molecular packing arrangement, which can in principle be obtained by grazing incidence X-ray diffraction or atomic force microscopy, whereas in bulk solids spontaneous resolution can be easily detected by various macroscopic methods. This short review provides analogies between spontaneous separation in 3-D and recent examples in 2-D, showing that spontaneous separation generally depends upon subtle differences in molecular structure. Chirality 10:415-424, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 160
    Electronic Resource
    Electronic Resource
    Determination of the rotational barriers of atropisomeric polychlorinated biphenyls (PCBs) by a novel stopped-flow multidimensional gas chromatographic techniqueThis article was orginally published in Chirality, Volume 10, Number 4, pages 316-320. As it is suited to the theme of this issue, this article appears again here. All citations to this article should use the original volume, issue, and page range. (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 425-429 
    Details
    ISSN: 0899-0042
    Keywords: atropisomeric polychlorinated biphenyls (PCBs) ; Chirasil-Dex ; rotational barrier ; stopped-flow multidimensional gas chromatographic technique ; on-line enantiomerization kinetics ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The rotational barriers ΔG† (T) of the four atropisomeric polychlorinated biphenyls (PCBs) 2,2′,3,5′,6-pentachlorobiphenyl (PCB 95), 2,2′3,3′,4,6′-hexachlorobiphenyl (PCB 132), 2,2′,3,3′,6,6′-hexachlorobiphenyl (PCB 136), and 2,2′,3,4′,5′,6-hexachlorobiphenyl (PCB 149) were determined via on-line enantiomerization kinetics by a new stopped-flow multidimensional gas chromatographic technique (stopped-flow MDGC) employing Chirasil-Dex as chiral stationary phase for enantiomer separation. The calculated rotational barriers ΔG† (T) of the trichloro-ortho-substituted atropisomers are 184 ± 2 kJ/mol for PCB 95, 189 ± 4 kJ/mol for PCB 132, and 184 ± 1 kJ/mol for PCB 149 at 300°C. The rotational barrier ΔG† (T) of tetrachloro-ortho-substituted PCB 136 is at least (or higher than) 210 kJ/mol at 320°C. Chirality 10:425-429, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 161
    Electronic Resource
    Electronic Resource
    Chiral recognition of phthalides and lactams (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 430-433 
    Details
    ISSN: 0899-0042
    Keywords: Whelk-O 1 ; chromatography ; HPLC ; enantiodifferentiation ; heterocycles ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In concert with a larger study of the processes by which chiral stationary phase CSP 1 differentiates between enantiomers, we have investigated the chromatographic separation of the enantiomers of a series of aryl-substituted heterocycles of systematically varied structure. A mechanistic picture of how these and similar resolutions occur is emerging. The mechanistic hypothesis described herein is of predictive value. Chirality 10:430-433, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 162
    Electronic Resource
    Electronic Resource
    Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 434-483 
    Details
    ISSN: 0899-0042
    Keywords: ristocetin A ; macrocyclic antibiotic ; enantiomeric separations ; underivatized amino acids ; chiral stationary phase ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The macrocyclic glycopeptide, ristocetin A, was covalently bonded to a silica gel support and evaluated as a liquid chromatographic (LC) chiral stationary phase (CSP). Over 230 racemates were resolved in either the reversed-phase mode, the normal-phase mode, or the polar-organic mode. The retention behavior and selectivity of this CSP were examined in each mode. Optimization of separations on this column is discussed. The ristocetin A CSP appeared to be complimentary to other glycopeptide CSPs (i.e., vancomycin and teicoplanin). Column stability was excellent. The CSP was not irreversibly altered when going from one mobile phase mode to another. Chirality 10:434-483, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 163
    Electronic Resource
    Electronic Resource
    Determination of the enantiomers of albuterol in human and canine plasma by enantioselective high-performance liquid chromatography on a teicoplanin-based chiral stationary phase (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 484-491 
    Details
    ISSN: 0899-0042
    Keywords: salbutamol ; chiral separation ; validated assay ; fluorescence detection ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A sensitive enantioselective high-performance chromatographic (HPLC) method was developed and validated to determine low levels of (-)-R and (+)-S-albuterol in plasma. Baseline resolution was achieved by using a teicoplanin-based chiral stationary phase with a polar organic mobile phase consisting of methanol/acetonitrile/glacial acetic acid/diethylamine, 40:60:0.3:0.2, (v/v/v/v) and a flow-rate of 1.0 ml/min. Enantioselectivity (α) equaled 1.18 and resolution (Rs) equaled 1.8. By using fluorescence detection maximized at 230 and 310 nm for excitation and emission, respectively, concentrations of each enantiomer could be measured down to 125 pg/ml from a 1-ml plasma sample. Initially, the method was applied to plasma samples from a small single-dose inhalation study of racemic albuterol in a human volunteer and, later, to in vivo samples from a canine inhalation study of the single enantiomer, (-)-R-albuterol. Results from the canine study showed that no chiral inversion of (-)-R-albuterol occurs in the dog. Chirality 10:484-491, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 164
    Electronic Resource
    Electronic Resource
    Achiral derivatization as a means of improving the chromatographic resolution of racemic alcohols on benzoylcellulose CSPs (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 492-498 
    Details
    ISSN: 0899-0042
    Keywords: racemate ; enantiomer ; HPLC ; chiral stationary phase ; benzoylcellulose ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The advantages that can be gained from derivatization of various racemic aliphatic and aromatic alcohols prior to enantiomeric chromatographic separation have been systematically investigated for a series of benzoate derivatives. Three cellulose-based CSPs available in the pure polymeric form - tribenzoyl cellulose (TBC), meta-methylbenzoyl cellulose (MMBC), and para-methylbenzoyl cellulose (PMBC) - were selected and several benzoate derivatives varying in the nature and the position of the substituent on the benzoyl group were prepared and analysed. TBC clearly gives the broadest application range, and among the different benzoate esters the best selectivity was generally obtained with either the 4-methoxybenzoate or the 4-methylbenzoate derivatives. Based on these results, some empirical rules could be formulated for optimizing the enantiomeric separation of racemic alcohols, which make up one of the most important classes of chemical substances used as drugs and biocides, or as building blocks for their synthesis. An application of this approach to the preparative separation of the enantiomers of a drug intermediate is also shown. Chirality 10:492-498, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 165
    Electronic Resource
    Electronic Resource
    Enantioselective capillary gas chromatography in the investigation of stereochemical correlations of terpenoids (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 499-504 
    Details
    ISSN: 0899-0042
    Keywords: enantioselective capillary gas chromatography ; cyclodextrin derivatives ; stereochemistry of terpenes ; monoterpenes ; essential oils ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Capillary gas chromatography employing the unique selectivities of specifically substituted cyclodextrins is highly suited for stereochemical investigations of terpenoid compounds. The analysis of many essential oils have shown that monoterpene derivatives regularly occur as enantiomeric mixtures. In the case of sesquiterpene hydrocarbons, liverworts (Hepaticae) and other lower organisms usually biosynthesize compounds of opposite stereochemistry as compared to higher plants and enantiomeric mixtures occur only occasionally. The investigation of diterpene hydrocarbons has so far shown no indication of the presence of both enantiomers in the same plant. Chirality 10:499-504, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 166
    Electronic Resource
    Electronic Resource
    Determination of drug levels in human serum by circular dichroism (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 507-512 
    Details
    ISSN: 0899-0042
    Keywords: chiroptical method ; drug analysis ; β-lactam antibiotics ; CD spectroscopy ; human fluids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A study of the applicability of circular dichroism (CD) for the determination of drug levels in human serum is described and a new method for the quantitative determination of optically active absorbing drugs having Cotton effects at wavelengths above 250 nm in human serum and/or plasma is proposed. The principal advantages of this method are speed, economy, and simplicity, no derivatization or chromatographic separation steps being needed. The validity of the CD determination was confirmed by analysis of variance, β-lactam antibiotics being chosen as model drugs. In addition, the validation studies performed confirm the accuracy and precision of the proposed method. For β-lactam antibiotics lacking Cotton effects above 250 nm, an alternative method based on the extraction of the drug from serum is considered. Chirality 10:507-512, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 167
    Electronic Resource
    Electronic Resource
    Unexpected difference in enantioselective retention on cellulase (CBH I) silica stationary phase caused by exchange of potassium for sodium ion in the mobile phase (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 513-518 
    Details
    ISSN: 0899-0042
    Keywords: CBH I ; cellulase ; cation ; sodium ; potassium ; enantioselectivity and temperature ; ionic strength ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An increase in both retention and enantioselectivity for some β-blocking agents was observed when exchanging potassium to sodium ion in the buffer used as mobile phase. A large effect of ionic strength on retention was observed, while the enantioselectivity was constant. Chirality 10:513-518, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 168
    Electronic Resource
    Electronic Resource
    Weak interactions and the tunneling racemization (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 519-521 
    Details
    ISSN: 0899-0042
    Keywords: optical activity of enantiomers ; weak interactions ; stability of optical activity ; racemization ; tunneling effect ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Assuming the active molecule as a two-level system, we calculate the racemization, due to the tunneling effect, taking into account the effects of the weak interactions and of an external potential. We show that the weak interactions would block the tunneling racemization of enantiomers in compressed gases and liquids. Chirality 10:519-521, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 169
    Electronic Resource
    Electronic Resource
    Structure and substituent effect on chiral separation of some 4a-methyl-2,3,4,4a-tetrahydro-1H-fluorene derivatives and 4a-methyl-1,2,3,4,4a,9a-hexahydro-fluoren-9-one derivatives on CTA-I and chiralcel OJ chiral stationary phases (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 522-527 
    Details
    ISSN: 0899-0042
    Keywords: chiral HPLC ; quantitative substituent effect ; recognition mechanism ; fluorene derivative-chiral separation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The chromatographic parameters for 12 structurally related compounds in the 4a-methyl-2,3,4,4a-tetrahydro-1H-fluorene and 4a-methyl-1,2,3,4,4a,9a-hexahydro-fluoren-9-one series are reported on CTA-I and Chiralcel OJ chiral stationary phases. Arrangement of the k' values according to configurationally related enantiomer series (Class I and Class II) and not according to the actual order of elution, allows the treatment of the data by linear correlation with structure and substituent effect. A detailed analysis of the capacity factor variation with respect to the structural changes shows clearly that the framework and substitution effects do not result in the same response on the two cellulose ester chiral stationary phases. More interestingly, it emerges that chiral discimination may be attributed to certain areas of the molecule, these areas being different in the interaction within CTA-I and Chiralcel OJ. Furthermore, our analysis points out the relevance of attempting to develop quantitative relationships for configurationally related series of enantiomers (in our case Class I and Class II), the main effort being devoted to the understanding of the capacity factor variation in each class rather than of the α values, which are derived entities. Chirality 10:522-527, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 170
    Electronic Resource
    Electronic Resource
    Drugs for chiral discrimination: Non-coded amino acids and dipeptides by asymmetric hydrogenation (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 535-539 
    Details
    ISSN: 0899-0042
    Keywords: asymmetric hydrogenation ; non-coded amino acids ; enantioselectivity ; dipeptides ; diastereoselectivity ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomers of Propranolol, Pindolol, and Carazolol, well-known β-blockers, have been used to prepare cationic aminophosphine phosphinite rhodium complexes. Propraphos-Rh and Pindophos-Rh are very efficient catalysts in the asymmetric hydrogenation of N-Boc-protected unusual dehydroamino acid derivatives. Carazolol-Rh is less suitable in both activity and enantioselectivity. Under the same conditions, N-Boc-protected dehydrodipeptides are hydrogenated with diastereoselectivities between 70 and 90% de. Chirality 10:535-539, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 171
    Electronic Resource
    Electronic Resource
    Extent of chiral inversion of the 2-arylpropionic acids by Cordyceps militaris (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 528-534 
    Details
    ISSN: 0899-0042
    Keywords: chiral inversion ; ibuprofen ; ketoprofen ; flurbiprofen ; indoprofen ; suprofen ; fenoprofen ; metabolism of 2-arylpropionic acids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The fungus Cordyceps militaris has been previously shown to be capable of inverting the chirality of 2-phenylpropionic acid from its (R)-enantiomer to its (S)-antipode. The structure of this compound is similar to the 2-arylpropionic acid non-steroidal anti-inflammatory drugs, which have also been reported to undergo a similar chiral inversion process in mammals and man. We report here an investigation into the substrate specificity of the enzyme system present in C. militaris using pure enantiomers and racemates of ibuprofen and ketoprofen and racemates of indoprofen, suprofen, flurbiprofen, and fenoprofen and the structurally related compounds 2-phenylbutyric acid and 2-phenoxypropionic acid as substrates, using optimised incubation conditions developed for the inversion of 2-phenylpropionic acid. The results demonstrated that C. militaris is capable of inverting the chirality of all the compounds investigated, which suggests that the active sites of the enzymes are very flexible with regard to the molecular dimensions of the substrate molecule and the spatial occupation of the groups surrounding the chiral centre. Metabolism of all the substrates was observed but the rate of metabolism varied extensively depending on the substrate. Achiral HPLC analysis was used to detect any potential metabolites and the results suggested that the site of the metabolism appeared to be at the aliphatic side groups only, with the aromatic ring being left intact in all cases. These results suggest that C. militaris could be a valuable tool in the investigation of the prospective metabolic fates of new 2-arylpropionic acids during their development. Chirality 10:528-534, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 172
    Electronic Resource
    Electronic Resource
    Gas chromatographic separation of PCB atropisomers on cyclodextrin stationary phases (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 540-547 
    Details
    ISSN: 0899-0042
    Keywords: chiral capillary columns ; PCB enantiomers ; temperature dependence of enantioselectivity ; effect of polysiloxane polarity on enantioselectivity ; enantiomeric ratio ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Gas chromatographic study on chiral separation of PCBs was performed in a series of capillary columns coated with 0.1-μm film of modified cyclodextrin (CD) stationary phases. The preparation of columns included the investigation into the effect of the content of cyclodextrin derivative in polysiloxane, the type of polysiloxane and temperature of analysis on the quality of separation and retention of atropisomers of 15 selected PCB congeners. The separation properties towards PCBs of stationary phase heptakis(2,3-di-O-methyl-6-O-tert-butyl-dimethylsilyl)-β-CD dissolved in SE-30, SE-54, and OV-1701, were compared with those of 6-monokis-octamethylene-permethyl-β-CD anchored to polydimethylsiloxane polymer (ChirasilDex column, Chrompack, Middelburg, The Netherlands) and octakis(2,6-di-O-methyl-3-O-pentyl)-γ-CD in OV-1701 (MEGA, Legnano (MI), Italy). The correctness of quantitative enantiomer ratio determination was assesed by splitless analysis of PCBs reference solutions in concentration of 1.25-125 ng/ml (PCBs 45 and 91) and 2.5-250 ng/ml (PCB 95) (the PCB congeners are numbered according to IUPAC). Chirality 10:540-547, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 173
    Electronic Resource
    Electronic Resource
    Eighth International Symposium on Chiral Discrimination (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 555-555 
    Details
    ISSN: 0899-0042
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No abstract.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 174
    Electronic Resource
    Electronic Resource
    Separation of enantiomers of drugs by capillary electrophoresis, part 7: Gamma-cyclodextrin as chiral solvating agent (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 548-554 
    Details
    ISSN: 0899-0042
    Keywords: capillary electrophoresis ; enantiomer separation ; chiral drugs ; γ-cyclodextrin ; gamma-cylcodextrin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Following an extended chiral drug screening program by capillary zone electrophoresis (CZE), the enantioseparation of 86 racemic drugs was tested with γ-cyclodextrin as a chiral solvating agent. Unified conditions were applied to all experiments. In total, 18 drug racemates were separated, 13 entries thereof that had not been separated at the lower CSA concentration applied in an earlier stage of the project. A comparison of the data with the results obtained for α- and β-cyclodextrin points to the significance of partial penetration (“side-on binding”) of aryl groups into the cyclodextrin cavity. Chirality 10:548-554, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 175
    Electronic Resource
    Electronic Resource
    Enantioselective synthesis of α-aminophosphonic acid derivatives by hydrogenation (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 564-572 
    Details
    ISSN: 0899-0042
    Keywords: asymmetric hydrogenation ; aminophosphine phosphinites ; rhodium complexes ; dehydro aminophosphonic acids ; NMR ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral α-aminophosphonic acid derivatives are efficiently synthesized by asymmetric hydrogenation of the prochiral N-acyl-α,β-dehydroaminophosphonates. PROPRAPHOS-Rh-catalysts from readily available (S)- and (R)-Propranolol proved to be suitable in the homogenous reaction affording an enantiomeric excess of 87-92% with high rate. The aminophosphonic acid derivatives and precursors were fully characterized by 1H, 13C, and 31P NMR spectroscopy. Chirality 10:564-572, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 176
    Electronic Resource
    Electronic Resource
    Synthesis and optical properties of the chloroquine enantiomers and their complexes with ferriprotoporphyrin IX in aqueous solution (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 556-563 
    Details
    ISSN: 0899-0042
    Keywords: chloroquine ; enantiomers ; synthesis ; pyroglutamic acid ; ferriprotoporphyrin IX ; circular dichroism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chloroquine (CQ) enantiomers were prepared by a novel synthesis starting from either (S)- or (R)-pyroglutamic acid. Light-absorption spectra of CQ and of complexes of ferriprotoporphyrin IX (FP) with CQ were measured in dilute aqueous solutions at pH 7.3 and 11.3. Spectrophotometric titrations at these pH values indicated a mole ratio of FP:CQ of 2:1 for the FP-CQ aggregated complexes. Aqueous solutions of each of the CQ enantiomers (pH 7.3) and of their complexes with FP (pH 11.3) were investigated by circular dichroism (CD). At pH 11.3, the complexes of the two enantiomers showed CD-band extrema of opposite sign at 409-410 nm. CD-titrations at pH 11.3 confirmed a predominant mole ratio of FP:CQ of 2:1 in the complex. The possible origin of the optical activity of the FP-CQ complexes is discussed. Chirality 10:556-563, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 177
    Electronic Resource
    Electronic Resource
    Preparative enantioseparation on polysaccharide phase using microporous silica as a support (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 573-577 
    Details
    ISSN: 0899-0042
    Keywords: hexahelicene ; sulphoxides ; carbohydrate carbamate ; chiral preparative ; silica ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The preparative enantiomeric resolutions of hexahelicen-7-yl acetic acid methyl ester and two sulphoxides were performed on cellulose tris(3,5-dimethylphenylcarbamate) coated onto aminopropylated 5-μm silica with 120-Å diameter pore. High enantiomeric purity was obtained for both enantiomers. The enantioselectivity of the amylose tris(3,5-dimethylphenylcarbamate), cellulose and amylose tris(phenylcarbamate) phases for the hexahelicen-7-yl acetic acid derivative were also investigated. Chirality 10:573-577, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 178
    Electronic Resource
    Electronic Resource
    Chirality and insect pheromones (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 578-586 
    Details
    ISSN: 0899-0042
    Keywords: bark beetle pheromone ; drugstore beetle pheromone ; enantioselective synthesis ; frontalin ; stegobinone ; stereochemistry-pheromone activity relationships ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantioselective synthesis is a central component of research on the effect of chirality on the relationships between pheromone structure and pheromone bioactivity. The syntheses of stegobinone, the drugstore beetle pheromone, and frontalin, a bark beetle pheromone, are reported as examples of stereocontrolled synthesis. Chirality governs the biodiversity of pheromone perception, as illustrated by the discussion on the relationships between absolute configuration and pheromone activity. Chirality 10:578-586, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 179
    Electronic Resource
    Electronic Resource
    Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 587-591 
    Details
    ISSN: 0899-0042
    Keywords: snuff ; chewing tobacco ; Turkish tobacco ; Burley tobacco ; Virginia tobacco ; transdermal patches ; gum ; nasal spray ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomeric composition of nicotine in 18 smokeless tobaccos, 3 strains of tobacco leaf, 8 pharmaceutical products, and 4 commercial reagents was determined. The relative amount of the minor enantiomeric component, (R)-(+)-nicotine, ranged from ∼0.1% to ∼1.2% of the total nicotine in all samples. In some cases it appears that (R)-(+)-nicotine may be considered one of the five most common alkaloids in tobacco products. The highest level of (R)-(+)-nicotine was found in a commercial transdermal patch. The extraction and purification processes used in obtaining commercial (S)-(-)-nicotine supplies from tobacco do not appear to decrease the amount of (R)-(+)-nicotine present. Chirality 10:587-591, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 180
    Electronic Resource
    Electronic Resource
    Molecular arrangements in chiral sheets of N-alkylcholamides bilayered crystals (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 600-618 
    Details
    ISSN: 0899-0042
    Keywords: steroidal bile acids ; inclusion compounds ; crystal structures ; facial molecules ; amphiphilic molecules ; amphiphilic sheets ; hydrogen-bonding networks ; head-to-tail ; head-to-head ; tail-to-tail ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral compounds, N-methyl-, N-ethyl-, and N-n-propylcholamides, form crystalline inclusion compounds with water or small organic substances. The compounds were analyzed by X-ray diffraction methods. It was found that the crystals have bilayered structures accumulated by chiral molecular sheets. The chiral molecules associate in a unique head-to-head/tail-to-tail and right-to-left motif to give chiral and amphiphilic sheets. Such sheets stack by adhesions between the hydrophilic sides and between the lipophilic sides. The alkyl groups of the amides prompt the formation of a hydrogen-bonding network between the tails instead of a cyclic one between the head and tail. The guest molecules are accommodated into small cavities between the steroidal side chains. Chirality 10:600-618, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 181
    Electronic Resource
    Electronic Resource
    Chiral recognition mechanism for the resolution of enantiomers on a highly effective HPLC chiral stationary phase derived from (R)-4-hydroxyphenylglycine (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 592-599 
    Details
    ISSN: 0899-0042
    Keywords: chiral separation ; chiral selector ; separation of enantiomers ; liquid chromatography ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A chiral stationary phase (CSP 1) prepared starting from (R)-4-hydroxyphenylglycine and then grafting (R)-N-butanoyl-4-allyloxyphenylglycine N-propyl amide to silica gel was found to be very effective in separating the enantiomers of N-(3,5-dinitrobenzoyl)-α-amino amides. From the chromatographic behaviors of the resolution of N-propyl amides, N,N-diethyl amides and ethyl esters of N-(3,5-dinitrobenzoyl)-α-amino acids and the resolution of various N-(substituted benzoyl)leucine N-propyl amides, the hydrogen bonding and the π-π donor-acceptor sites of the analyte for the interaction with the CSP have been proposed. Similarly, the hydrogen bonding donor and acceptor sites of the CSP for the interaction with the analyte have been proposed from the comparison of the chromatographic behaviors of the resolution of various N-(3,5-dinitrobenzoyl)-α-amino N-propyl amides on modified CSPs (CSP 7 containing trifluoroacetyl group instead of the butanoyl group of CSP 1 and CSP 8 containing N,N-diethyl group instead of the N-propyl group of CSP 1) with those on CSP 1. By correlating the interaction sites of the CSP and their complementary interaction sites of the analyte, a chiral recognition mechanism which utilizes the two hydrogen bonding interactions and the π-π donor-acceptor interaction between (R)-CSP 1 and more retained analytes, (S)-N-(3,5-dinitrobenzoyl)-α-amino amides, has been proposed. Chirality 10:592-599, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 182
    Electronic Resource
    Electronic Resource
    1-Arylfluorenols: Convenient preparation via the ester-mediated nucleophilic aromatic substitution protocol, facile racemization, and intrinsic chiral induction ability (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 619-626 
    Details
    ISSN: 0899-0042
    Keywords: nucleophilic aromatic substitution ; optical resolution ; asymmetric synthesis ; diastereoselective reaction ; Grignard reaction ; atrolactic acid derivatives ; biaryl coupling reaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Novel 1-aryl-9H-fluoren-9-ols 1 were conveniently synthesized by using the ester-mediated nucleophilic aromatic substitution on 2,6-dimethoxybenzoate 2 by aryl Grignard reagents as the key step. Racemic 1-phenylfluorenol 1a was converted to the diastereomeric esters 8 of (S)-2′-methoxy-1,1′-binaphthyl-2-carboxylic acid, which were readily separable by silica-gel column chromatography. Reduction of the optically pure diastereomer (+)-8 with LiAlH4 accompanied an appreciable racemization to give (+)-1a of 89% ee, which provides the first isolation of an optically active fluorenol of defined enantiomeric purity. Intrinsic chiral induction abilities of the 9-fluorenols 1 were examined in the atrolactic acid synthesis from phenylglyoxylates 9 and methylmagnesium iodide with diastereoselectivity of up to 85% de and the binaphthyl coupling of 1-methoxy-2-naphthoates 11 with 2-methoxy-1-naphthylmagnesium bromide with up to 73% de. Chirality 10:619-626, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 183
    Electronic Resource
    Electronic Resource
    Evaluation of the macrocyclic antibiotic avoparcin as a new chiral selector for HPLC (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 627-660 
    Details
    ISSN: 0899-0042
    Keywords: avoparcin ; macrocyclic antibiotics ; enantiomeric separations ; chiral stationary phases ; verapamil ; thyroxine ; mephenytoin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Avoparcin is a macrocyclic glycopeptide antibiotic structurally related to vancomycin, teicoplanin, and ristocetin A. When attached to 5-μm spherical silica gel, the avoparcin proved to be an effective chiral stationary phase (CSP) that could be used in the reversed-phase, normal-phase, and polar-organic modes. The avoparcin CSP was complimentary to the other macrocyclic glycopeptide CSPs in that it could resolve some racemates that the others could not, and vice versa. Some important compounds resolved on the avoparcin CSP include verapamil, thyroxine, mephenytoin, and 2-imidazolidone-4-carboxylic acid. The use of this CSP and the optimization of separations on it are discussed. Avoparcin appears to be a useful addition to this family of CSPs. Chirality 10:627-660, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 184
    Electronic Resource
    Electronic Resource
    Chiral dendrimers with axial chirality (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 661-666 
    Details
    ISSN: 0899-0042
    Keywords: chiral dendrimers ; dendrimers ; axial chirality ; (R)-(+)-1,1′-bi-2,2′-naphthol ; optical rotation ; circular dichroism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and optical activity of novel chiral dendrimers with axial chirality are reported. The dendrimers were constructed by coupling of the polyether dendritic bromides with (R)-(+)-1,1′-bi-2-naphthol (1). The uniform (2, 3, 4) and non-uniform double-O-alkylated (8, 9, 10) as well as mono-O-alkylated (5, 6, 7) products were thus obtained. These chiral molecules were characterized by 1H- and 13C-NMR, elemental analysis, optical rotation, adsorption spectra, and circular dichroism. It was found that the specific rotation decreases with the increase of the number of generation for each group of dendrimers (2-4, 5-7, and 8-10, respectively). In terms of the molar rotation, it was quite different; the molar rotation increased sharply for dendrimers, 2-4, but only slightly for dendrimers 5-7. The dihedral angle change of bi-naphthyl in the synthesized dendrimers was discussed based on the CD spectra. Chirality 10:661-666, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 185
    Electronic Resource
    Electronic Resource
    A chemoenzymatic synthesis of the O-glycosides (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 676-681 
    Details
    ISSN: 0899-0042
    Keywords: β-glucosidase from almond ; reverse hydrolysis ; transglucosylation ; enantioselectivity ; enantiomeric excess ; absolute configuration ; alkyl β-D-glucopyranoside ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Almond β-glucosidase was used to catalyze the synthesis of alkyl β-d-glucopyranosides 1b-3b starting from either d-glucose (4) or phenyl-β-d-glucopyranoside (5) and the racemic alcohols 1a-3a. The enzymic reactions were provided in different acetonitrile/water mixtures [9:1 (v/v) for the reverse hydrolysis, and 1:9 (v/v) for the transglycosylation]. Both enzymic reactions, that is, the reverse hydrolysis and the transglucosylation, are enantioselective processes. The enantiomeric purity of products 1b-2b of the enzymic reactions varied between 75 and 86% ee, the values of which were based on the analysis of the aglyconic parts (1c-2c) of the alkyl β-d-glucopyranoside molecules (1b-2b). Chirality 10:676-681, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 186
    Electronic Resource
    Electronic Resource
    Near-UV, circular dichroism, and fluorescence spectra of a rigid rodlike helical polysilane bearing trietheral moiety in ethanol/water (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 667-675 
    Details
    ISSN: 0899-0042
    Keywords: polysilane ; circular dichroism ; exciton couplet ; helix ; fluorescence ; poor solvent ; good solvent ; conformational property ; helix reversal ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An optically active, rigid rodlike helical polysilane with 6,9,12-trioxatetradecyl and (S)-2-methylbutyl substituents (1) was newly obtained as a very high molecular weight polymer of several million. Due to the presence of trietheral substituent, 1 was readily soluble in a polar solvent such as ethanol and a mixture of ethanol and water, but was insoluble in pure water. Polysilane 1 in pure ethanol at room temperature exhibited an intense and narrow ultraviolet (UV) and circular dichroism (CD) absorptions at 323 nm, associated with an almost mirror imaged fluorescence (FL) at 328 nm, that are characteristic of rigid rodlike, single-screw-sense helical polysilanes reported previously. When solution temperature was changed from 60°C to -104°C, a global shape of 1 expanded associated with an increase of segment length, whereas a screw pitch tended to be wound tightly. On the other hand, as a solvent polarity became poor, a global shape of 1 shrunk associated with an decrease of segment length and formed a chiral motif with an M-helicity between two helical segments with a kink. At a ratio of 50% of ethanol/water of 50:50 (v/v), 1 became insoluble and formed aggregates. Chirality 10:667-675, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 14 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 187
    Electronic Resource
    Electronic Resource
    Lipase catalyzed transesterification of 2-substituted 3-hydroxy esters (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 693-698 
    Details
    ISSN: 0899-0042
    Keywords: Pseudomonas cepacia ; lipase PS ; transesterification ; kinetic resolution ; 2-substituted 3-hydroxy ester ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Kinetic resolution of 2-substituted 3-hydroxy esters was examined by lipase PS catalyzed transesterification using vinyl acetate as an acyl donor. Resolution of (±)-syn- and -anti-1a, -1e possessing a small methyl group at the C-3 position was accomplished enantioselectively. The outcome of the resolution seems to be related to the differences in size of the substituents at the stereocenter bearing a secondary hydroxy group. Chirality 10:693-698, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 188
    Electronic Resource
    Electronic Resource
    Optically active chlorohydrins as chiral C3 and C4 building units: Microbial resolution and synthetic applications (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 682-692 
    Details
    ISSN: 0899-0042
    Keywords: optically active ; epichlorohydrin ; 3-chloro-1,2-propanediol ; microbial resolution ; dehalogenation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Production of highly optically active C3 and C4 chlorohydrins was developed by using the bacteria stereoselectively dehalogenating and assimilating the racemic substrate: Pseudomonas sp. and Alcaligenes sp. These bacteria stereoselectively assimilate (RS)-2,3-dichloro-1-propanol (DCP) and (RS)-3-chloro-1,2-propanediol (CPD) followed by microbial preparation of (R)- and (S)-DCP, and (R)- and (S)-CPD with 〉99% ee. A novel dehalogenating enzyme, halohydrin dehydro-dehalogenase from one of the above strains, Alcaligenes sp. DS-S-7G, was applicable for preparation of optically active 1,2-diols with 60-99% ee. Moreover, microbial resolution of C4 chlorohydrins with whole cells of Pseudomonas sp. was carried out. This resolution reaction using the resting cells gave (R)- and (S)-4-chloro-3-hydroxybutyrate (CHB) and (S)-4-chloro-3-hydroxybutyronitrile (BN) with 〉98% ee. In the case of the resting cells of Enterobacter sp., both (R)-CHB (〉99% ee) and (S)-3-hydroxy-γ-butyrolactone (95% ee) with excellent yield were obtained. Also, some typical synthetic applications using the above chiral C3 and C4 synthons were introduced: ferroelectric liquid crystals, optically active β-blockers, and other chiral pharmaceuticals. Chirality 10:682-692, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 189
    Electronic Resource
    Electronic Resource
    High-speed separation of ormeloxifene enantiomers using sulfated β-cyclodextrin in capillary electrophoresis (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 699-704 
    Details
    ISSN: 0899-0042
    Keywords: ormeloxifene ; chiral separation ; sulfated cyclodextrin ; enantiomers ; capillary electrophoresis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (-)-Ormeloxifene, a drug candidate under development, was separated from (+)-ormeloxifene using capillary electrophoresis (CE) with sulfated β-cyclodextrin as chiral buffer additive. With conventional long-end injection the method showed high efficiency, since the theoretical plate number for (-)-ormeloxifene was over 1 million per m and the enantiomeric resolution was more than 100. However, the relatively long separation time of ∼22 min was a limiting factor. In order to reduce separation time, short-end injection experiments were carried out. By using the instrumental limits for capillary dimensions and field strength, the separation time was reduced to 〈40 sec. A further and significant reduction was achieved by applying extended short-end injection, which is a novel injection technique presented in this paper. With the extended short-end injection procedure, a plug of run buffer is injected after the sample has been injected, thus moving the sample closer to the detector and resulting in very short effective capillary lengths. Using the extended short-end injection technique, the separation was performed on 1.8 cm capillary (effective length) and the enantiomers were separated within 10 sec, which is a reduction of the original separation time by a factor of ∼155. Chirality 10:699-704, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 190
    Electronic Resource
    Electronic Resource
    Ideal enantiomeric resolution (Preferential Enrichment) by recrystallization of a racemic compound. V: Relationship between Preferential Enrichment and crystal structures (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 705-710 
    Details
    ISSN: 0899-0042
    Keywords: preferential enrichment ; enantiomeric enrichment ; mixed crystal ; solid solution ; racemic compound crystals ; X-ray crystallography ; chiral ammonium sulfonate ; reversal of chirality ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The X-ray crystal structure of (±)-[2-[4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoyl]ethyl]dimethylammonium p-nitrobenzenesulfonate [(±)-NNMe2], which shows the novel enantiomeric resolution phenomenon Preferential Enrichment, has been compared with that of (±)-[2-[4-(3-ethoxy-2-hydroxypropoxy) phenylcarbamoyl]ethyl]dimethylammonium p-toluenesulfonate [(±)-NTMe2], which does not show the phenomenon. The stable crystalline form of (±)-NNMe2 is a racemic compound, while that of (±)-NTMe2 is a mixed (disordered) crystal composed of the two enantiomers. The intermolecular hydrogen bonding mode in the crystal of (±)-NNMe2 was very different from that of (±)-NTMe2. Chirality 10:705-710, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 191
    Electronic Resource
    Electronic Resource
    Asymmetric activation of chiral BINOL-zirconium catalysts: Effect of a product-like activator (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 717-721 
    Details
    ISSN: 0899-0042
    Keywords: zirconium ; binaphthol (BINOL) ; allylation ; asymmetric activation ; enantioselective carbon-carbon bond formation ; chiral high-performance liquid chromatography ; induction period ; product-like activator ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The asymmetric activation of binaphthol (BINOL)-zirconium catalysts is described on the enantioselective allylation of benzaldehyde with allyltin reagents. This model reaction has been used with the intention of establishing a protocol for a zirconium-based catalyst system, to be followed by structural studies. Initial results are reported that characterise a number of interesting features, namely the influence of an induction period and a high level of asymmetric activation obtained after addition of a product-like activator. Chirality 10:717-721, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 192
    Electronic Resource
    Electronic Resource
    Stereospecific anionic polymerization of chiral benzyl α-[(1-phenylethoxy)methyl]acrylate (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 711-716 
    Details
    ISSN: 0899-0042
    Keywords: stereospecific polymerization ; chiral α-substituted acrylate ; stereoregularity ; chiroptical property ; isotactic polymer ; regular arrangement ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A novel chiral monomer, benzyl α-[(1-phenylethoxy)methyl]acrylate was synthesized, and the stereoregularity and chiroptical property of the polymers obtained by radical and anionic polymerizations were investigated. Anionic polymerization in toluene provided a polymer with high isotacticity regardless of optical purity of the monomer and difference of counter cations, Li+ and Mg2+, while radical polymerization appears to yield an atactic polymer. The isotactic copolymers anionically obtained from a mixture of (R)- and (S)-monomers showed peak splitting probably due to the triad arrangement of (R) and (S) groups of side chains in the resonance of 13C-NMR spectra. The isotactic polymer prepared from enantiomerically pure (R)-monomer ([α] 25 365 = +157°) with n-BuLi in toluene exhibited higher specific rotation ([α] 25 365 = +262°) than that of the radical polymer ([α] 25 365 = +162°). This may be explained by regular arrangement of optically active groups along the polymer chain of the isotactic polymer. Chirality 10:711-716, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 193
    Electronic Resource
    Electronic Resource
    Editors' note (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. iii 
    Details
    ISSN: 0899-0042
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No abstract.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 194
    Electronic Resource
    Electronic Resource
    Enthalpies of mixing of R- and S- enantiomers of propane-1,2-diol and methyllactate at 298.15 K (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 722-725 
    Details
    ISSN: 0899-0042
    Keywords: R- and S-isomer ; chiral compound ; enthalpy of mixing ; propane-1,2-diol ; methyllactate ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enthalpies of mixing of chiral isomers R- and S- of propane-1,2-diol and methyllactate, respectively, have been measured over the whole range of mole fraction at 298.15 K. All the enthalpies of mixing measured are very small. The enthalpic differences between the interactions of molecules of like-configuration and those of opposite configuration have been evaluated precisely. Mixing of R- and S-enantiomers of propane-1,2-diol gives slight enthalpic stabilisation over the whole range of mole fraction, however methyllactate has shown the opposite effect on mixing. Chirality 10:722-725, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 195
    Electronic Resource
    Electronic Resource
    Synthesis and polymerization of benzyl (3R,4R)-3-methylmalolactonate via enzymatic preparation of the chiral precursor (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 727-733 
    Details
    ISSN: 0899-0042
    Keywords: β-methylaspartase ; biocatalysis ; (2S,3R)-3-methylaspartic acid ; benzyl (3R,4R)-3-methylmalolactonate ; (3R,4R)-3-methylmalolactonic acid ; poly[benzyl β-(2R,3S)-3-methylmalate] ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: β-methylaspartate ammonia-lyase, EC 4.3.1.2, (β-methylaspartase) from Clostridium tetanomorphum was used to produce a 40/60 molar ratio of (2S,3R) and (2S,3S)-3-methylaspartic acids, 2a and 2b, respectively, from mesaconic acid 1 as substrate, on a large scale. To prepare (3R,4R)-3-methyl-4-(benzyloxycarbonyl)-2-oxetanone (benzyl 3-methylmalolactonate) 6, 2a and 2b were transformed, in the first step, into 2-bromo-3-methylsuccinic acids 3a and 3b and separated. After three further steps, (2S,3S)-3a yielded the α,β-substituted β-lactone (3R,4R) 6 with a very high diastereoisomeric excess (〉95% by chiral gas chromatography). The corresponding crystalline polymer, poly[benzyl β-(2R,3S)-3-methylmalate] 8, prepared by an anionic ring opening polymerization, was highly isotactic as determined by 13C NMR. Catalytic hydrogenolysis of lactone 6 yielded (3R,4R)-3-methyl-4-carboxy-2-oxetanone (3-methylmalolactonic acid) 7, to which reactive, chiral, or bioactive molecules can be attached through ester bonds leading to polymers with possible therapeutic applications. Because of the ability of β-methylaspartase to catalyse both syn- and anti-elimination of ammonia from (2S,3RS)-3-methylaspartic acid 2ab at different rates, the (2S,3R)-stereoisomer 2a was retained and isolated for further reactions. These results permit the use of the chemoenzymatic route for the preparation of both optically active and racemic polymers of 3-methylmalic acid with well-defined enantiomeric and diastereoisomeric compositions. Chirality 10:727-733, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 196
    Electronic Resource
    Electronic Resource
    Self-assembly of dideoxyguanosine (3′,3′) and (5′,5′)-monophosphates (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 734-741 
    Details
    ISSN: 0899-0042
    Keywords: liquid crystals ; circular dichroism ; X-ray diffraction ; self-recognition ; salt ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The title compounds show a pronounced cation-directed ability to self-assemble in water and to gives columnar structures similar to four-stranded helices; for compound (5′→5′)-d(GpG), this leads to the formation of cholesteric and hexagonal liquid crystalline phases. Both phases are columnar and the cholesteric phase is left-handed. This behaviour is a further confirmation of the tendency of guanine derivatives to self-assemble to give stacked columnar structures whenever not impossible for structural reasons. The CD spectra of the aggregates in isotropic solutions are dominated by a negative exciton couplet centred around 250 nm associated to a left-handed columnar chirality. The shapes of the profiles, in the 220-300-nm region, for (5′→5′)-d(GpG) (in water or in saline solutions) and for (3′→3′)-d(GpG) (in KCl solution) are quasi-mirror images of those of poly(G) and (3′→5′)-d(GpG). The appearance of relatively intense CD signals around 280-300 nm in solution of (3′→3′)-d(GpG) in the presence of NaCl resembles that of (3′→5′)-d(GpG) in the presence of Rb+ or Na+. In the compounds investigated in this work, which present two equivalent ends, one observes the two CD features that have been associated, in the current literature, with the signature of four-stranded parallel and antiparallel structures: hence the origin of these CD bands cannot be found in the polarity of the strands. Self-assembly is favoured by the addition of extra salt and the stabilising effect of K+ is greater than that of Na+, in the case of (3′→3′)-d(GpG), an assembled species could be detected by CD only in the presence of extra salt. Chirality 10:734-741, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 197
    Electronic Resource
    Electronic Resource
    Association equilibrium of d-methamphetamine and l-methamphetamine with serum albumin (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 742-746 
    Details
    ISSN: 0899-0042
    Keywords: methamphetamine ; enantiomer ; serum albumin ; CD spectra ; association equilibrium ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The association equilibria for complex formation between serum albumin (bovine, rat) and the optical isomers of methamphetamine (MAMP) was determined using an ultrafiltration method. It was found that serum albumin/d-MAMP and serum albumin/l-MAMP complexes had distinctly different Scatchard plots with bovine and rat albumin. The binding parameters of each association equilibrium were estimated from the Scatchard plots by Rosenthal's graphic method. This distinguished two kinds of specific binding sites in terms of the association equilibrium between bovine serum albumin and d-MAMP, and one binding site for rat serum albumin and d-MAMP. One specific binding site was found between serum albumin and l-MAMP in both bovine and rat. Molar ellipticities, [θ], of peaks were decreased in the CD spectra of the complexes formed between bovine serum albumin and d-MAMP or l-MAMP when compared with the CD spectrum of bovine serum albumin alone. However, no difference in [θ] was found between the CD spectra of the enantiomers of MAMP in the measured wavelength range. The non-specific binding site was distinct from the specific binding site and resulting from altered tertiary structure of the albumin molecule. Chirality 10:742-746, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 198
    Electronic Resource
    Electronic Resource
    Stereoselective chiral inversion of pantoprazole enantiomers after separate doses to rats (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 747-753 
    Details
    ISSN: 0899-0042
    Keywords: pantoprazole ; proton pump inhibitor ; chiral inversion ; stereoselective pharmacokinetics ; rats ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (±)-Pantoprazole ((±)-PAN), (±)-5-(difluoromethoxy)-2-[[(3.4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole is a chiral sulfoxide that is used clinically as a racemic mixture. The disposition kinetics of (+)-PAN and (-)-PAN given separately has been studied in rats. Serum levels of (+)- and (-)-PAN and its metabolites, pantoprazole sulfone (PAN-SO2), pantoprazole sulfide (PAN-S), 4′-O-demethyl pantoprazole sulfone (DMPAN-SO2), and 4′-O-demethyl pantoprazole sulfide (DMPAN-S) were measured by HPLC. Following single intravenous or oral administration, both enantiomers were rapidly absorbed and metabolized, resulting in similar serum concentrations, suggesting that the two enantiomers have approximately the same disposition kinetics. The major metabolite of both (+)- and (-)-PAN was PAN-SO2, while DMPAN-SO2 was also detected as a minor metabolite. Serum levels of PAN-S and DMPAN-S could not be quantified after intravenous or oral administration of either enantiomer.Significant chiral inversion occurred after intravenous and oral administration of (+)-PAN. The AUCs of (-)-PAN after intravenous and oral dosing of (+)-PAN were 36.3 and 28.1%, respectively of those of total [(+) + (-)] PAN. In contrast, the serum levels of (+)-PAN were below quantitation limits after intravenous or oral administration of (-)-PAN. Therefore, chiral inversion was observed only after administration of (+)-PAN, supporting the hypothesis that stereoselective inversion from (+)-PAN to (-)-PAN occurs in rats. Chirality 10:747-753, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 199
    Electronic Resource
    Electronic Resource
    Studies on the enantioselective retention mechanisms of cellobiohydrolase I (CBH I) by covalent modification of the intact and fragmented protein (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 760-769 
    Details
    ISSN: 0899-0042
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In order to elucidate the chiral recognition mechanisms of the enzyme cellobiohydrolase I (CBH I), its carboxylic groups were covalently modified. The synthetic modification was carried out either in the presence or absence of cellobiose, which has proven to inhibit the enzymatic activity and if present in the mobile phase impairs enantioselectivity of amino alcohols. Compared to the reference CSP (unmodified CBH-I silica and CBH-I core silica), the synthetically modified phases show differences both in enantioselectivity and retention. The enzymatic differences between the CSPs were also in line with the chromatographic results. The selectivity factors of propranolol are almost unchanged during the reaction periods in the presence of cellobiose, while they decreased rapidly without the inhibitor. In one case, even a slight improvement in enantioselectivity was obtained, indicating that non-stereospecific carboxylic groups were ruled out. Chirality 10:760-769, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
  • 200
    Electronic Resource
    Electronic Resource
    Amphiphilic proline and prolylproline derivatives in the rhodium(I)-catalyzed asymmetric hydrogenation in water: Chiral induction as indication of the location of reactants within the micelle (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 754-759 
    Details
    ISSN: 0899-0042
    Keywords: solubilization ; enhanced enantioselectivity ; chiral induction ; critical micellar concentration ; reaction place ; function of proline ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Proline and prolylproline dipeptide derived surfactants promote the asymmetric hydrogenation of (Z)-methyl α-acetamidocinnamate in water in the presence of the catalytic system [Rh(cod)2]BF4 + BPPM. Activity and enantioselectivity are enhanced significantly and the results in water are similar to those obtained with organic solvents. The possibility of a chiral induction was investigated in the presence of the optically active amino acid and peptide amphiphiles and an achiral rhodium catalyst [Rh(bdpb)(cod)]BF4. The analysis of the low optical induction gave some indications of the site where the reaction takes place within the micelle. Selected critical micelle concentrations (cmc) of the new prepared surfactants were determined by surface tension measurements. Chirality 10:754-759, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
Close ⊗
This website uses cookies and the analysis tool Matomo. More information can be found here...