STEREOSELECTIVE EFFECT OF WARFARIN AND BILIRUBIN ON THE BINDING OF 5-(ORTHO-CHLOROPHENYL)-1,3-DIHYDRO-3-METHYL-7-NITRO-2H-1,4-BENZODIAZEPIN-2-ONE ENANTIOMERS TO HUMAN SERUM-ALBUMIN

被引:11
作者
FITOS, I
VISY, J
MAGYAR, A
KAJTAR, J
SIMONYI, M
机构
[1] HUNGARIAN ACAD SCI, CENT RES INST CHEM, POB 17, H-1525 BUDAPEST, HUNGARY
[2] EOTVOS LORAND UNIV, INST ORGAN CHEM, H-1364 BUDAPEST 5, HUNGARY
关键词
affinity chromatography; allosteric interaction; increased enantioselectivity; protein binding; resolution;
D O I
10.1002/chir.530020307
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The binding of the title benzodiazepine enantiomers and its modulation by warfarin and bilirubin were studied by chromatography on human serum albumin (HSA) immobilized on Sepharose 4B, and also by a combination of ultrafiltration and circular dichroism (UF‐CD) methods. In the absence of warfarin and bilirubin the binding of the benzodiazepine was not stereoselective. (S)‐Benzodiazepine and (S)‐warfarin mutually increased the binding of each other, while the binding of (R)‐benzodiazepine was preferentially enhanced on HSA saturated with bilirubin. Copyright © 1990 Wiley‐Liss, Inc.
引用
收藏
页码:161 / 166
页数:6
相关论文
共 18 条
[1]   CIRCULAR-DICHROISM AND GEL-FILTRATION STUDY OF BINDING OF PROCHIRAL AND CHIRAL 1,4-BENZODIAZEPIN-2-ONES TO HUMAN-SERUM ALBUMIN [J].
ALEBICKOLBAH, T ;
KAJFEZ, F ;
RENDIC, S ;
SUNJIC, V ;
KONOWAL, A ;
SNATZKE, G .
BIOCHEMICAL PHARMACOLOGY, 1979, 28 (16) :2457-2464
[2]  
BRODERSEN R, 1979, CRC CR REV CL LAB SC, V11, P305
[3]  
BRODERSEN R, 1977, J BIOL CHEM, V252, P5067
[4]   A STUDY ON THE ALLOSTERIC INTERACTION BETWEEN THE MAJOR BINDING-SITES OF HUMAN-SERUM ALBUMIN USING MICROCALORIMETRY [J].
DROGE, JHM ;
JANSSEN, LHM ;
WILTING, J .
BIOCHIMICA ET BIOPHYSICA ACTA, 1985, 827 (03) :396-402
[5]   BINDING OF 3-ALKYL-1,4-BENZODIAZEPIN-2-ONE STEREOISOMERS TO HUMAN-SERUM ALBUMIN [J].
FITOS, I ;
SIMONYI, M ;
TEGYEY, Z ;
KAJTAR, M ;
OTVOS, L .
ARCHIV DER PHARMAZIE, 1986, 319 (08) :744-749
[6]   SELECTIVE EFFECT OF CLONAZEPAM AND (S)-UXEPAM ON THE BINDING OF WARFARIN ENANTIOMERS TO HUMAN-SERUM ALBUMIN [J].
FITOS, I ;
SIMONYI, M .
JOURNAL OF CHROMATOGRAPHY, 1988, 450 (02) :217-220
[7]   INVERSE STEREOSELECTIVITY IN THE BINDING OF ACENOCOUMAROL TO HUMAN-SERUM ALBUMIN AND TO ALPHA-1-ACID GLYCOPROTEIN [J].
FITOS, I ;
VISY, J ;
MAGYAR, A ;
KAJTAR, J ;
SIMONYI, M .
BIOCHEMICAL PHARMACOLOGY, 1989, 38 (14) :2259-2262
[8]   STEREOSELECTIVE BINDING OF "3-ACETOXY-1,4-BENZODIAZEPINE-2-ONES AND "3-HYDROXY-1,4-BENZODIAZEPINE-2-ONES TO HUMAN-SERUM ALBUMIN - SELECTIVE ALLOSTERIC INTERACTION WITH WARFARIN ENANTIOMERS [J].
FITOS, I ;
TEGYEY, Z ;
SIMONYI, M ;
SJOHOLM, I ;
LARSSON, T ;
LAGERCRANTZ, C .
BIOCHEMICAL PHARMACOLOGY, 1986, 35 (02) :263-269
[9]  
FITOS I, 1988, CHROMATOGRPAHY 87, P205
[10]  
FITOS I, 1986, BIOORGANIC HETEROCYC, P275