Synthesis and cytotoxicity of analogues of the antibiotic BE 10988 inhibitors of DNA topoisomerase II

被引:13
作者
Catrycke, MO
Houssin, R
Hénichart, JP
Pfeiffer, B
Renard, P
Dassonneville, L
Bailly, C
机构
[1] Ctr Oscar Lambret, Lab Pharmacol Antitumorale, F-59045 Lille, France
[2] INSERM, U524, IRCL, F-59045 Lille, France
[3] Univ Lille 2, Inst Chim Pharmaceut, F-59006 Lille, France
[4] ADIR, F-92415 Courbevoie, France
关键词
D O I
10.1016/S0960-894X(99)00307-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Indolequinone derivatives of the antitumour antibiotic BE 10988 were synthesized and evaluated for their cytotoxicity and action mechanism. The quinone system is essential to biological activity and the thiazole ring plays a major role in the poisoning of topoisomerase II. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2025 / 2030
页数:6
相关论文
共 19 条
[1]   BIOLOGICAL-ACTIVITY AND MOLECULAR INTERACTION OF A NETROPSIN ACRIDINE HYBRID LIGAND WITH CHROMATIN AND TOPOISOMERASE II [J].
BAILLY, C ;
COLLYNDHOOGHE, M ;
LANTOINE, D ;
FOURNIER, C ;
HECQUET, B ;
FOSSE, P ;
SAUCIER, JM ;
COLSON, P ;
HOUSSIER, C ;
HENICHART, JP .
BIOCHEMICAL PHARMACOLOGY, 1992, 43 (03) :457-466
[2]   DEPSIPEPTIDE ANALOGS OF THE ANTITUMOR DRUG DISTAMYCIN CONTAINING THIAZOLE AMINO-ACIDS RESIDUES [J].
BAILLY, C ;
HOUSSIN, R ;
BERNIER, JL ;
HENICHART, JP .
TETRAHEDRON, 1988, 44 (18) :5833-5843
[3]   Indolequinone antitumor agents: Relationship between quinone structure and rate of metabolism by recombinant human NQO1 [J].
Beall, HD ;
Hudnott, AR ;
Winski, S ;
Siegel, D ;
Swann, E ;
Ross, D ;
Moody, CJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :545-548
[4]   Indolequinone antitumor agents:: Correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity [J].
Beall, HD ;
Winski, S ;
Swann, E ;
Hudnott, AR ;
Cotterill, AS ;
O'Sullivan, N ;
Green, SJ ;
Bien, R ;
Siegel, D ;
Ross, D ;
Moody, CJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4755-4766
[5]  
Everett SA, 1998, ANTI-CANCER DRUG DES, V13, P635
[6]   STIMULATION OF SITE-SPECIFIC TOPOISOMERASE II-MEDIATED DNA CLEAVAGE BY AN N-METHYLPYRROLECARBOXAMIDE-ANILINOACRIDINE CONJUGATE - RELATION TO DNA-BINDING [J].
FOSSE, P ;
RENE, B ;
SAUCIER, JM ;
HENICHART, JP ;
WARING, MJ ;
COLSON, P ;
HOUSSIER, C ;
BAILLY, C .
BIOCHEMISTRY, 1994, 33 (33) :9865-9874
[7]   SYNTHETIC MODEL OF A BLEOMYCIN METAL-COMPLEX [J].
HENICHART, JP ;
HOUSSIN, R ;
BERNIER, JL ;
CATTEAU, JP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (22) :1295-1297
[8]  
Henichart JP, 1997, MOL PHARMACOL, V51, P448
[9]  
Jaffar M, 1998, ANTI-CANCER DRUG DES, V13, P593
[10]   CARBOXYLATION AND ACYLATION OF 4,7-DIMETHOXYINDOLES AND A STUDY OF THE CORRESPONDING DEALKYLATED DERIVATIVES [J].
MALESANI, G ;
CHIARELOTTO, G ;
FERLIN, MG ;
MASIERO, S .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (03) :613-617