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  • 1
    Electronic Resource
    Electronic Resource
    Phenytoin-induced alteration in the N-dechloroethylation of ifosfamide stereoisomers (1997)
    Springer
    Cancer chemotherapy and pharmacology 40 (1997), S. 531-533 
    Details
    ISSN: 1432-0843
    Keywords: Key words CYP2B6 ; Ifosfamide ; Phenytoin ; Metabolic induction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract  Case: A suspected alteration in ifosfamide (IFF) metabolism and pharmacokinetics was observed in a pediatric patient receiving phenytoin. Methods: Sequential plasma samples were obtained and analyzed for the concentrations of the enantiomers of IFF and their N-dechloroethylated metabolites (DCE-IFF) using a validated enantioselective gas chromatographic-mass spectrometric method. Results: In the phenytoin-treated patient, the metabolic formation of IFF enantiomers was increased and the metabolic pattern of the N-dechloroethylation altered from non-phenytoin-treated patients: (R)-3-DCE IFF*(S)-3-DCE-IFF = (S)-2-DCE-IFF〉(R)-2-DCE-IFF (control) vs (S)-3-DCE-IFF = (S)-2-DCE-IFF〉(R)-3-DCE-IFF*(R)-2-DCE-IFF (patient). Conclusions: Previous studies have attributed the production of the (S)-2-DCE-IFF and (S)-3-DCE-IFF metabolites to the activity of CYP2B6 and (R)-2-DCE-IFF and (R)-3-DCE-IFF to the activity of CYP3A4. The results suggest that phenytoin induced the activity of CYP2B6 to a greater extent than CYP3A4. In addition, the patient, who was at least partially refractory to several other treatments, went into remission after IFF treatment suggesting that phenytoin pretreatment might increase IFF therapeutic efficacy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002800050698
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  • 2
    Electronic Resource
    Electronic Resource
    Enantioselective separation of enantiomeric amides on three amylose-based chiral stationary phases: Effects of backbone and carbamate side chain chiralities (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 173-177 
    Details
    ISSN: 0899-0042
    Keywords: chiral high-performance liquid chromatography ; polysaccharides ; structure-retention relationships ; amides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of enantiomeric amides have been chromatographed on three amylose-based chiral stationary phases (CSPs): amylose tris(3,5-dimethylphenylcarbamate) (AD-CSP), amylose tris (S-phenylethylcarbamate) (AS-CSP), and amylose tris(R-phenylethyl-carbamate) (AR-CSP). The relative retentions and enantioselectives of the solutes on the three CSPs were compared and basic structure-retention relationships developed to describe the chromatographic results. The data indicate that for these solutes the observed elution order was a function of the chirality of the amylose backbone, while the magnitude of the enantioselective separations was affected by the chirality of the carbamate side chain. Chirality 9:173-177, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 3
    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
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  • 4
    Electronic Resource
    Electronic Resource
    Determination of the enantiomeric composition of mexiletine and its four hydroxylated metabolites in urine by enantioselective capillary gas chromatography (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 30-34 
    Details
    ISSN: 0899-0042
    Keywords: gas chromatography ; modified β-cyclodextrin column ; chiral separation ; assay ; mexiletine ; hydroxylated metabolites ; urine ; conjugation/deconjugation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomers of mexiletine and four of its hydroxylated metabolites were directly separated by capillary gas chromatography using a heptakis(6-O-tert-butyl-dimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin column. The method was applied to the analysis of urine samples from cancer patients who were treated with racemic mexiletine as part of a study of the use of mexiletine in the relief of neuropathic pain. Samples analyzed before and after deconjugation of the urine with β-glucuronidase/arylsulfatase showed a high stereoselectivity in the formation and conjugation of these compounds. © 1996 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Enantioselective separation of cyclic chiral ketones and their corresponding diastereomeric alcohols by HPLC on chiral and chiral/chiral coupled stationary phases (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 551-555 
    Details
    ISSN: 0899-0042
    Keywords: amylose tris-3,5-dimethylphenyl carbamate CSP {AD-CSP} ; cellulose tris-3,5-dimethylphenyl carbamate CSP {ODH-CSP} ; enantioselective HPLC ; coupled column chromatography ; Chemistry ; Food Science, Agricultural, Medicinal and Pharmaceutical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantioselective HPLC methods have been developed for the resolution of (RS)-2-phenylcyclohexanone (compound 1) and (RS)-2-phenyltetrahydropyran-4-one (compound 4) and the diastereoselective and enantioselective separations of their respective cis- and trans-alcohols; reduction of compound 1 yields trans- and cis-2-phenyl-1-cyclohexanol (compounds 2 and 3, respectively) and reduction of compound 4 yields trans- and cis-2-phenyl-tetrahydropyran-4-ol (compounds 5 and 6, respectively). Compounds 1, 2, and 3 were stereochemically resolved using a chiral stationary phase (CSP) based upon amylose tris(3,5-dimethylphenyl carbamate) coated on 10 μm silica-gel (Chiralpak AD-CSP). Compounds 4, 5, and 6 were stereochemically resolved on a coupled column system where a column containing a CSP based upon cellulose tris(3,5-dimethylphenyl carbamate) coated on 5 μm silica (Chiralcel OD-H-CSP) was coupled in series to the AD-CSP. The strategy employed in the identification of the peaks in the respective chromatograms is also discussed in this presentation. Chirality 8:551-555, 1996. © 1997 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    The 1996 chirality debate (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 95-95 
    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
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  • 7
    Electronic Resource
    Electronic Resource
    Is chiral recognition a three-point process? (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 96-98 
    Details
    ISSN: 0899-0042
    Keywords: enantioselectivity ; stereospecificity ; chiral separations ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: No abstract.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Application of an in vitro system in the study of chemotherapeutic drug effects on DNA replication (1996)
    New York, N.Y. : Wiley-Blackwell
    Journal of Cellular Biochemistry 61 (1996), S. 444-451 
    Details
    ISSN: 0730-2312
    Keywords: in vitro DNA replication ; mammalian ; doxorubicin ; araC ; progesterone ; Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: DNA replication machinery is an important target for chemotherapeutic drugs. We have used an in vitro system to study the effect of drugs on mammalian DNA replication, either by direct interaction with the DNA structure or with replication proteins and machinery. The anthracycline doxorubicin (Dox) showed a dose-dependent inhibitory effect on DNA replication, whether incubated with HeLa cell extracts or with DNA and nucleotides. Earliest-labeled fragment analysis revealed that inhibition of replication began within the origin-containing fragment in both control and Dox-containing reactions in vitro. AraC, a nucleoside analog, had no significant effect on DNA synthesis. In contrast, araCTP was able to inhibit DNA replication in vitro. Since metabolism is diminished in this in vitro system, the degree of phosphorylation of araC was apparently low. Progesterone showed an increase in nucleotide incorporation (sensitive to BuPdGTP inhibition of replication-specific polymerases α and δ) after preincubation with HeLa cell extracts, although progesterone receptors were not detectable in the HeLa cell extracts. In addition, we observed an inhibition in DNA replication when progesterone was preincubated with DNA and nucleotides. These results suggest that progesterone may have a mechanism of action that is different from any known to be mediated through progesterone receptors. In conclusion, these results indicate that this mammalian in vitro replication system will be useful for the study of mechanisms and design of therapeutic drugs that inhibit mammalian DNA replication. © 1996 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Receptor independent effects on DNA replication by steroids (1998)
    New York, N.Y. : Wiley-Blackwell
    Journal of Cellular Biochemistry 70 (1998), S. 323-329 
    Details
    ISSN: 0730-2312
    Keywords: steroids ; DNA replication ; carcinogenesis ; proliferation ; cell-free system ; Life and Medical Sciences ; Cell & Developmental Biology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: There is now convincing evidence associating estrogens with an increased risk of some cancers. However, the absence of a complete correlation between estrogen receptor binding and the biological activity of these estrogens has suggested the possibility of other mechanisms of action. The effect on DNA replication of several hormones that are putatively involved in breast cancer was tested at a physiological concentration. The studies were conducted in a HeLa cell-free system by using a plasmid containing a specific mammalian origin of replication (DHFR oriβ〈0R) as template DNA. A series of related steroids produced an entire range of activity from enhancement to inhibition of in vitro DNA replication. These studies indicate a new possible target, which may help to better understand the effect of these hormones in breast cancer. Furthermore, the results show that this in vitro DNA replication system provides an evaluative assay for the effects of compounds on hormone-responsive cancers independent of some hormone receptors. J. Cell. Biochem. 70:323-329, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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