Synthesis, anti-HIV activity and stability studies of 3′-azido-2′,3′-dideoxythymidine 5′-fluorophosphate

被引:4
|
作者
Egron, D
Arzumanov, AA
Dyatkina, NB
Krayevsky, A
Imbach, JL
Aubertin, AM
Gosselin, G
Périgaud, C
机构
[1] Univ Montpellier 2, Lab Chim Biorgan, UMR CNRS USTL 5625, F-34095 Montpellier 5, France
[2] Russian Acad Sci, Engelhardt Inst Mol Biol, Moscow 117984, Russia
[3] Univ Strasbourg 1, Inst Virol, INSERM U74, F-67000 Strasbourg, France
来源
NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 4-5期
关键词
D O I
10.1080/15257779908041621
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 synthesis, in vitro anti-HIV activity, and stability studies of AZT 5'-fluorophosphate (F-AZTMP) are reported. The present results demonstrate that such compound is a bioprecursor of its parent 5'-mononucleotide (AZTMP) but its biotransformation does not allow its selective intracellular delivery. Moreover, several attempts were carried out in order to improve the biological activity of this compound by the use of a SATE prodrug strategy.
引用
收藏
页码:983 / 984
页数:2
相关论文
共 50 条
  • [31] On the design of polymeric 5′-O-ester prodrugs of 3′-azido-2′,3′-dideoxythymidine (AZT)
    Troev, Kolio D.
    Mitova, Violeta A.
    Ivanov, Ivan G.
    TETRAHEDRON LETTERS, 2010, 51 (47) : 6123 - 6125
  • [33] CLINICAL-PHARMACOLOGY OF 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE (ZIDOVUDINE) AND RELATED DIDEOXYNUCLEOSIDES
    YARCHOAN, R
    MITSUYA, H
    MYERS, CE
    BRODER, S
    NEW ENGLAND JOURNAL OF MEDICINE, 1989, 321 (11): : 726 - 738
  • [34] Novel approaches for designing 5′-O-ester prodrugs of 3'-azido-2′,3′-dideoxythymidine (AZT)
    Parang, K
    Wiebe, LI
    Knaus, EE
    CURRENT MEDICINAL CHEMISTRY, 2000, 7 (10) : 995 - 1039
  • [35] SYNTHESIS AND ANTI-HIV ACTIVITY OF STEROIDAL PRODRUGS OF 3'-AZIDO-3'-DEOXYTHYMIDINE (AZT)
    BALAGOPALA, MI
    OLLAPALLY, AP
    LEE, HJ
    CELLULAR AND MOLECULAR BIOLOGY, 1995, 41 : S1 - S7
  • [36] SYNTHESIS OF 3'-AZIDO-2',3'-DIDEOXYRIBOFURANOSYLPURINES
    IMAZAWA, M
    ECKSTEIN, F
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15): : 3044 - 3048
  • [37] TREATMENT OF HUMAN IMMUNODEFICIENCY VIRUS RELATED POLYNEUROPATHY WITH 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE
    DALAKAS, MC
    YARCHOAN, R
    SPITZER, R
    ELDER, G
    SEVER, JL
    ANNALS OF NEUROLOGY, 1988, 23 : S92 - S94
  • [38] THE ANTIRETROVIRAL AND CYTOSTATIC ACTIVITY, AND METABOLISM OF 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE, 3'-FLUORO-2',3'-DIDEOXYTHYMIDINE AND 2',3'-DIDEOXYCYTIDINE ARE HIGHLY CELL TYPE-DEPENDENT
    BALZARINI, J
    MATTHES, E
    MEEUS, P
    JOHNS, DG
    DECLERCQ, E
    PURINE AND PYRIMIDINE METABOLISM IN MAN VI, PT B: BASIC RESEARCH AND EXPERIMENTAL BIOLOGY, 1989, 253 : 407 - 413
  • [39] SYNTHESIS, ANTI-HIV ACTIVITY, AND BIOLOGICAL PROPERTIES OF 2',3'-DIDEHYDRO-2',3'-DIDEOXYTHYMIDINE (D4T)
    MARTIN, JC
    MANSURI, MM
    STARRETT, JE
    SOMMADOSSI, JP
    BRANKOVAN, V
    GHAZZOULI, I
    HO, HT
    HITCHCOCK, MJM
    NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (5-6): : 841 - 844
  • [40] SYNTHESIS OF 1-(3'-AZIDO-2',3'-DIDEOXY-ALPHA-L-THREO-PENTOFURANOSYL)THYMINE AS A POTENTIAL ANTI-HIV AGENT
    CZERNECKI, S
    LEDIGUARHER, T
    SYNTHESIS-STUTTGART, 1991, (09): : 683 - 686