SUBSTRATE-SPECIFICITY OF ESCHERICHIA-COLI THYMIDINE PHOSPHORYLASE FOR PYRIMIDINE NUCLEOSIDES WITH ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS ACTIVITY

被引:15
作者
SCHINAZI, RF
PECK, A
SOMMADOSSI, JP
机构
[1] EMORY UNIV,SCH MED,DEPT PEDIAT,BIOCHEM PHARMACOL LAB,ATLANTA,GA 30322
[2] UNIV ALABAMA,DEPT PHARMACOL,DIV CLIN PHARMACOL,CTR AIDS RES,BIRMINGHAM,AL 35294
关键词
D O I
10.1016/0006-2952(92)90001-Y
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Various nucleoside antiviral agents and their metabolites were examined for their ability to be cleaved across the glycosidic bond by Escherichia coli thymidine phosphorylase. The increasing order of susceptibility to cleavage was U > T >> C derivatives. Nucleosides that were unsaturated in the sugar moiety were more susceptible than saturated ones. 3'-Deoxy-2',3'-didehydrothymidine was a substrate, whereas 3'-azido-, 3'-fluoro-, 3'-oxo- and 3'-thiapyrimidine nucleosides were resistant to this enzyme.
引用
收藏
页码:199 / 204
页数:6
相关论文
共 24 条
[1]   INSITU COMPLEXATION DIRECTS THE STEREOCHEMISTRY OF N-GLYCOSYLATION IN THE SYNTHESIS OF OXATHIOLANYL AND DIOXOLANYL NUCLEOSIDE ANALOGS [J].
CHOI, WB ;
WILSON, LJ ;
YEOLA, S ;
LIOTTA, DC ;
SCHINAZI, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9377-9379
[2]   ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE (-)-(1'R,4'R)-DIOXOLANE-THYMINE AND ITS ANTI-HIV ACTIVITY [J].
CHU, CK ;
AHN, SK ;
KIM, HO ;
BEACH, JW ;
ALVES, AJ ;
JEONG, LS ;
ISLAM, Q ;
VANROEY, P ;
SCHINAZI, RF .
TETRAHEDRON LETTERS, 1991, 32 (31) :3791-3794
[3]   STRUCTURE ACTIVITY RELATIONSHIPS OF PYRIMIDINE NUCLEOSIDES AS ANTIVIRAL AGENTS FOR HUMAN IMMUNODEFICIENCY VIRUS TYPE-1 IN PERIPHERAL-BLOOD MONONUCLEAR-CELLS [J].
CHU, CK ;
SCHINAZI, RF ;
AHN, MK ;
ULLAS, GV ;
GU, ZP .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) :612-617
[4]   COMPARATIVE ACTIVITY OF 2',3'-SATURATED AND UNSATURATED PYRIMIDINE AND PURINE NUCLEOSIDES AGAINST HUMAN IMMUNODEFICIENCY VIRUS TYPE-1 IN PERIPHERAL-BLOOD MONONUCLEAR-CELLS [J].
CHU, CK ;
SCHINAZI, RF ;
ARNOLD, BH ;
CANNON, DL ;
DOBOSZEWSKI, B ;
BHADTI, VB ;
GU, ZP .
BIOCHEMICAL PHARMACOLOGY, 1988, 37 (19) :3543-3548
[5]   INITIAL STUDIES ON THE CELLULAR PHARMACOLOGY OF 2',3'-DIDEOXYCYTIDINE, AN INHIBITOR OF HTLV-III INFECTIVITY [J].
COONEY, DA ;
DALAL, M ;
MITSUYA, H ;
MCMAHON, JB ;
NADKARNI, M ;
BALZARINI, J ;
BRODER, S ;
JOHNS, DG .
BIOCHEMICAL PHARMACOLOGY, 1986, 35 (13) :2065-2068
[6]   SELENIUM NUCLEOPHILES FOR THE PREPARATION OF ANTIVIRAL NUCLEOSIDES [J].
COSFORD, NDP ;
SCHINAZI, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2161-2165
[7]  
CRETTON EM, 1991, MOL PHARMACOL, V39, P258
[8]   PHARMACOKINETICS OF 3'-AZIDO-3'-DEOXYTHYMIDINE AND ITS CATABOLITES AND INTERACTIONS WITH PROBENECID IN RHESUS-MONKEYS [J].
CRETTON, EM ;
SCHINAZI, RF ;
MCCLURE, HM ;
ANDERSON, DC ;
SOMMADOSSI, JP .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1991, 35 (05) :801-807
[9]  
CRETTON EM, IN PRESS BIOCH PHARM
[10]   INHIBITION OF THE REPLICATION OF HEPATITIS-B VIRUS INVITRO BY 2',3'-DIDEOXY-3'-THIACYTIDINE AND RELATED ANALOGS [J].
DOONG, SL ;
TSAI, CH ;
SCHINAZI, RF ;
LIOTTA, DC ;
CHENG, YC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (19) :8495-8499