Synthesis and biological evaluation of 6',7'-dihydroxybergamottin (6,7-DHB), a naturally occurring inhibitor of cytochrome P450 3A4

被引：18
作者：
Bellevue, FH
Woster, PM
Edwards, DJ
He, K
Hollenberg, PF
机构：
[1] WAYNE STATE UNIV, DEPT PHARMACEUT SCI, DETROIT, MI 48202 USA
[2] WAYNE STATE UNIV, DEPT PHARM PRACTICE, DETROIT, MI 48202 USA
[3] UNIV MICHIGAN, DEPT PHARMACOL, ANN ARBOR, MI 49109 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1997年 / 7卷 / 20期
关键词：
D O I：
10.1016/S0960-894X(97)10043-9
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The recently isolated inhibitor of cytochrome P450 CYP3A4, 6',7'-dihydroxybergamottin (6,7-DHB), was synthesized by an efficient route that is readily adaptable to the production of analogues. The compound was evaluated as an inhibitor of 3A4 in a purified enzyme preparation, as well as against human liver microsomes and human 3A4 expressed in Escherichia coli membrane. In each case, 6,7-DHB proved to be a potent NADPH-and time dependent inactivator of 3A4. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：2593 / 2598
页数：6
相关论文
共 23 条
  • [1] INTERACTION OF CITRUS JUICES WITH FELODIPINE AND NIFEDIPINE
    BAILEY, DG
    SPENCE, JD
    MUNOZ, C
    ARNOLD, JMO
    [J]. LANCET, 1991, 337 (8736) : 268 - 269
  • [2] Coexpression of a human P450 (CYP3A4) and P450 reductase generates a highly functional monooxygenase system in Escherichia coli
    Blake, JAR
    Pritchard, M
    Ding, SH
    Smith, GCM
    Burchell, B
    Wolf, CR
    Friedberg, T
    [J]. FEBS LETTERS, 1996, 397 (2-3) : 210 - 214
  • [3] Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins
    Cai, YN
    BaerDubowska, W
    AshwoodSmith, MJ
    Ceska, O
    Tachibana, S
    DiGiovanni, J
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (04) : 729 - 736
  • [4] CHATTERJEE A, 1961, J CHEM SOC, P2246
  • [5] CHEMOTAXONOMY OF RUTACEAE .9. COUMARINS OF CITRUS-MACROPTERA
    DREYER, DL
    HUEY, PF
    [J]. PHYTOCHEMISTRY, 1973, 12 (12) : 3011 - 3013
  • [6] TROUGH CONCENTRATIONS OF CYCLOSPORINE IN BLOOD FOLLOWING ADMINISTRATION WITH GRAPEFRUIT JUICE
    DUCHARME, MP
    PROVENZANO, R
    DEHOORNESMITH, M
    EDWARDS, DJ
    [J]. BRITISH JOURNAL OF CLINICAL PHARMACOLOGY, 1993, 36 (05) : 457 - 459
  • [7] DISPOSITION OF INTRAVENOUS AND ORAL CYCLOSPORINE AFTER ADMINISTRATION WITH GRAPEFRUIT JUICE
    DUCHARME, MP
    WARBASSE, LH
    EDWARDS, DJ
    [J]. CLINICAL PHARMACOLOGY & THERAPEUTICS, 1995, 57 (05) : 485 - 491
  • [8] Edwards DJ, 1996, DRUG METAB DISPOS, V24, P1287
  • [9] GUENGERICH P, 1990, CARCINOGENESIS, V2, P2276
  • [10] IDENTIFICATION OF RIFAMPIN-INDUCIBLE P450IIIA4 (CYP3A4) IN HUMAN SMALL-BOWEL ENTEROCYTES
    KOLARS, JC
    SCHMIEDLINREN, P
    SCHUETZ, JD
    FANG, C
    WATKINS, PB
    [J]. JOURNAL OF CLINICAL INVESTIGATION, 1992, 90 (05) : 1871 - 1878
123