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  • Articles: DFG German National Licenses  (4)
  • Electronic Resource  (4)
  • antimalarial agents  (2)
  • protein binding  (2)
  • 1
    Electronic Resource
    Electronic Resource
    The in Situ Acetylation of an Immobilized Human Serum Albumin Chiral Stationary Phase for High-Performance Liquid Chromatography in the Examination of Drug–Protein Binding Phenomena (1992)
    Springer
    Pharmaceutical research 9 (1992), S. 480-484 
    Details
    ISSN: 1573-904X
    Keywords: chiral stationary phases ; human serum albumin ; protein binding ; binding sites ; high-performance liquid chromatography ; immobilized proteins ; chemical modification
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The in situ modification of an immobilized human serum albumin (HSA) high-performance liquid chromatographic chiral stationary phase by p-nitrophenyl acetate is reported. This procedure, which is thought to affect primarily a single reactive tyrosine residue within the protein structure, influenced the chromatographic retention and enantioselectivity factors of a wide range of solutes. For certain solutes, increases in both capacity factor and chiral resolution were observed. Ultrafiltration studies on representative test solutes using free HSA, treated in a similar manner to the immobilized protein, gave similar results as the chromatographic observations, indicating that the latter effects are not artifactual results of immobilization. The effect of the modification of HSA on the binding behavior of drugs reportedly sharing the site predominantly affected by the derivatization, namely, the indole–benzodiazepine binding site, varied greatly. This observation suggests that the affected binding area is not a single, tightly structurally defined site.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1015884112039
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Chiral resolution of some antimalarial agents by sub- and supercritical fluid chromatography on an (S)-naphthylurea stationary phase (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 173-180 
    Details
    ISSN: 0899-0042
    Keywords: (S)-naphthylurea chiral stationary phase ; subcritical fluid chromatography ; supercritical fluid chromatography ; antimalarial agents ; enantiomeric separations ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The behavior of mefloquine, halofantrine, enpiroline, quinine, quinidine, chloroquine and primaquine is studied by subcritical fluid chromatography on a (S)-naphthylurea column (250 mm × 4.6 mm ID) with a subcritical mobile phase composed of carbon dioxide, methanol and triethylamine (flow rate of 3 ml/min). Except for primaquine and chloroquine, each enantiomer was separated at a temperature between 40 and 60°C, and at a pressure below 15 MPa. A 98/2, v/v CO2/methanol 0.1% triethylamine mixture allowed the separation of halofantrine enantiomers while the enantiomers of the more polar metabolite (N-desbutylhalofantrine) were separated with a 80-20 v/v mixture as used for mefloquine, enpiroline, quinine and quinidine. The influence of temperature, pressure and of the nature of the mobile phase is discussed. © 1993 Wiley-Liss, Inc.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530050313
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Immobilized serum albumin: Rapid HPLC probe of stereoselective protein-binding interactions (1990)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 2 (1990), S. 263-268 
    Details
    ISSN: 0899-0042
    Keywords: protein binding ; stereoselectivity ; immobilized human serum albumin ; HPLC chiral stationary phase ; chiral drugs ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A human serum albumin-based HPLC chiral stationary phase (HSA-CSP) has been examined as a tool to investigate binding of chiral drugs to HSA and drug-drug protein-binding interactions. Rac-oxazepam hemisuccinate (OXH) was used as a model compound and the chromatographic retention (k′) of its enantiomers was determined after addition of displacers to the mobile phase. Compounds known to bind at the same site as OXH and at different sites were tested for their displacing capacities. Competitive binding interactions between the OXH enantiomers and displacers in the mobile phase were reflected by decreases in the k′s of (R)- and (S)-OXH. The results indicate that retention on the HSA-CSP accurately reflects binding to native HSA and the technique can determine enantioselective and competitive binding interactions at specific sites on HSA. The HSA-CSP was also able to recognize separate binding areas for (S)- and (R)-OXH.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530020412
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  • 4
    Electronic Resource
    Electronic Resource
    Enantioselective chromatography of the antimalarial agents chloroquine, mefloquine, and enpiroline on a α1 -acid glycoprotein chiral stationary phase: Evidence for a multiple-site chiral recognition mechanism (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 4 (1992), S. 30-35 
    Details
    ISSN: 0899-0042
    Keywords: chiral liquid chromatography ; α1 -acid glycoprotein ; antimalarial agents ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The effect of mobile phase pH and dimethyloctylamine (DMOA) on the retention (k') and stereoselectivity (α) of antimalarial agents mefloquine, enpiroline, and chloroquine on the α1-acid glycoprotein chiral stationary phase (AGP-CSP) was investigated. An increase of k' with increasing pH was observed while the effect on α was a function of the solute. The magnitude and direction of changes induced by DMOA depended on pH and the structure of the solute.The results of this study are consistent with a change of the conformation of the AGP between pH 5 and 7. At pH 7, the effect of DMOA on mefloquine was relatively well described by a competitive displacement from one enantioselective site. The effect on chloroquine and enpiroline suggests a multiple-site mechanism in which both competitive and allosteric interactions are involved.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530040108
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    Paper (German National Licenses)
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