CHEMISTRY AND ANTI-HIV ACTIVITY OF 2'-BETA-FLUORO-2',3'-DIDEOXYGUANOSINE

被引:7
作者
FORD, H
DRISCOLL, JS
SIDDIQUI, M
KELLEY, JA
MITSUYA, H
SHIRASAKA, T
JOHNS, DG
MARQUEZ, VE
机构
[1] NCI,DEV THERAPEUT PROGRAM,MED CHEM LAB,BETHESDA,MD 20892
[2] NCI,DIV CANC TREATMENT,CLIN ONCOL PROGRAM,MED BRANCH,EXPTL RETROVIROL SECT,BETHESDA,MD 20892
来源
NUCLEOSIDES & NUCLEOTIDES | 1994年 / 13卷 / 1-3期
关键词
D O I
10.1080/15257779408013236
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The 2'-beta-fluoro analogue of 2',3'-dideoxyguanosine has been prepared by two synthetic routes. This compound and two analogues have anti-HIV activity in at least two of three host cell systems used (ATH8, CEM, PEL). These compounds, as well as their ddGuo parents, have been characterized with regard to their acid-stabilities, octanol-water partition coefficients, and enzyme substrate properties for adenosine deaminase and purine nucleoside phosphorylase. F-ddGuo analogues are less potent but more stable than their non-fluorinated parent compounds.
引用
收藏
页码:213 / 234
页数:22
相关论文
共 44 条
[1]   INHIBITORS OF IMP DEHYDROGENASE STIMULATE THE PHOSPHORYLATION OF THE ANTIVIRAL NUCLEOSIDE 2',3'-DIDEOXYGUANOSINE [J].
AHLUWALIA, G ;
COONEY, DA ;
BONDOC, LL ;
CURRENS, MJ ;
FORD, H ;
JOHNS, DG ;
MITSUYA, H ;
FRIDLAND, A .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 171 (03) :1297-1303
[2]  
ANDERSON BD, 1992, J CONTROL RELEASE, V19, P219, DOI 10.1016/0168-3659(92)90078-6
[3]   INVITRO INHIBITION OF HEPATITIS-B VIRUS-REPLICATION BY 2',3'-DIDEOXYGUANOSINE, 2',3'-DIDEOXYINOSINE, AND 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE IN 2.2.15 (PR) CELLS [J].
AOKISEI, S ;
OBRIEN, MC ;
FORD, H ;
FUJII, H ;
GILBERT, DA ;
COONEY, DA ;
JOHNS, DG ;
BRODER, S ;
MITSUYA, H .
JOURNAL OF INFECTIOUS DISEASES, 1991, 164 (05) :843-851
[4]   6-METHOXYPURINE ARABINOSIDE AS A SELECTIVE AND POTENT INHIBITOR OF VARICELLA-ZOSTER VIRUS [J].
AVERETT, DR ;
KOSZALKA, GW ;
FYFE, JA ;
ROBERTS, GB ;
PURIFOY, DJM ;
KRENITSKY, TA .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1991, 35 (05) :851-857
[5]   CLINICAL-PHARMACOLOGY OF 2',3'-DIDEOXYINOSINE IN HUMAN IMMUNODEFICIENCY VIRUS-INFECTED CHILDREN [J].
BALIS, FM ;
PIZZO, PA ;
BUTLER, KM ;
HAWKINS, ME ;
BROUWERS, P ;
HUSSON, RN ;
JACOBSEN, F ;
BLANEY, SM ;
GRESS, J ;
JAROSINSKI, P ;
POPLACK, DG .
JOURNAL OF INFECTIOUS DISEASES, 1992, 165 (01) :99-104
[6]  
BALZARINI J, 1989, PURINE PYRIMIDINE B, V6, P407
[7]   POTENTIAL ANTI-AIDS DRUGS - LIPOPHILIC, ADENOSINE DEAMINASE-ACTIVATED PRODRUGS [J].
BARCHI, JJ ;
MARQUEZ, VE ;
DRISCOLL, JS ;
FORD, H ;
MITSUYA, H ;
SHIRASAKA, T ;
AOKI, S ;
KELLEY, JA .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) :1647-1655
[8]  
BONDOC LL, 1992, MOL PHARMACOL, V42, P525
[9]   CELLULAR PHARMACOLOGY AND ANTI-HIV ACTIVITY OF 2',3'-DIDEOXYGUANOSINE [J].
BUSSO, ME ;
RESNICK, L ;
YANG, BH ;
MIAN, AM .
AIDS RESEARCH AND HUMAN RETROVIRUSES, 1990, 6 (09) :1139-1146
[10]  
CHASSY BM, 1967, J BIOL CHEM, V242, P3655