STEREOCHEMICAL FEATURES OF 1,4-BENZODIAZEPIN-2-ONES BOUND TO HUMAN SERUM-ALBUMIN - DIFFERENCE CD AND UV STUDIES

被引:17
作者
BERTUCCI, C [1 ]
DOMENICI, E [1 ]
SALVADORI, P [1 ]
机构
[1] UNIV PISA,DIPARTIMENTO CHIM & CHIM IND,CNR,I-56126 PISA,ITALY
关键词
benzodiazepines; chiral discrimination; circular dichroism; difference spectroscopy; electronic absorption spectra; human serum albumin; stereospecific interaction;
D O I
10.1002/chir.530020308
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The stereochemistry of an achiral (Diazepam) and two chiral (3‐methyl and 3‐succinyloxy substituted) 1,4‐benzodiazepin‐2‐ones interacting with human serum albumin (HSA) has been investigated by making use of difference absorption (UV) and circular dichroism (CD) spectroscopies. Evidence is obtained for a higher affinity with HSA for one of the two possible conformations of the seven‐membered benzodiazepine ring. The red shift revealed by the absorption difference spectrum between the free and the bound drug accounts for the CD difference spectra observed. Copyright © 1990 Wiley‐Liss, Inc.
引用
收藏
页码:167 / 174
页数:8
相关论文
共 16 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]  
Bellot J L, 1981, Soins Gynecol Obstet Pueric, P3
[3]   STEREOCHEMISTRY OF ENZYMIC 3-HYDROXYLATION OF 1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES [J].
CORBELLA, A ;
GARIBOLDI, P ;
JOMMI, G ;
FORGIONE, A ;
MARCUCCI, F ;
MARTELLI, P ;
MUSSINI, E ;
MAURI, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (19) :721-722
[4]   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
[5]   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
[6]  
GUILBAUD P, 1978, STUD BIOPHYS, V69, P193
[7]   GENERAL-APPROACH TO CHIROPTICAL CHARACTERIZATION OF BINDING OF PROCHIRAL AND CHIRAL 1,4-BENZODIAZEPIN-2-ONES TO HUMAN-SERUM ALBUMIN [J].
KONOWAL, A ;
SNATZKE, G ;
ALEBICKOLBAH, T ;
KAJFEZ, F ;
RENDIC, S ;
SUNJIC, V .
BIOCHEMICAL PHARMACOLOGY, 1979, 28 (20) :3109-3113
[8]  
KRAGHHANSEN U, 1981, PHARMACOL REV, V33, P17
[9]  
MARUYAMA K, 1985, CHEM PHARM BULL, V33, P5002
[10]  
MULLER WE, 1975, MOL PHARMACOL, V11, P52