Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents

被引：39

作者：

Cai, Wen ^{[2
]}

Hassani, Mary ^{[1
]}

Karki, Rajesh ^{[2
]}

Walter, Ervin D. ^{[2
]}

Koelsch, Katherine H. ^{[1
]}

Seradj, Hassan ^{[2
]}

Lineswala, Jayana P. ^{[2
]}

Mirzaei, Hamid ^{[2
]}

York, Jeremy S. ^{[2
]}

Olang, Fatemeh ^{[2
]}

Sedighi, Minoo ^{[2
]}

Lucas, Jennifer S. ^{[2
]}

Eads, Thomas J. ^{[2
]}

Rose, Anthony S. ^{[2
]}

Charkhzarrin, Sahba ^{[2
]}

Hermann, Nicholas G. ^{[2
]}

Beall, Howard D. ^{[1
]}

Behforouz, Mohammad ^{[2
]}

机构：

[1] Univ Montana, Dept Biomed & Pharmaceut Sci, Ctr Environm Hlth Sci, Missoula, MT 59812 USA

[2] Ball State Univ, Dept Chem, Muncie, IN 47306 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 05期

基金：

美国国家卫生研究院;

关键词：

Lavendamycin analogues; Quinoline-5,8-diones; Antitumor; NQO1; Cytotoxicity; NAD(P)H-QUINONE OXIDOREDUCTASE-1 NQO1; METHYL-ESTER; DT-DIAPHORASE; STREPTONIGRIN BIOSYNTHESIS; STREPTOMYCES-LAVENDULAE; QUINONE STRUCTURE; CELL-LINES; ANALOGS; QUINOLINE-5,8-DIONES; OXYGEN;

D O I：

10.1016/j.bmc.2010.01.037

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：

A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were prepared through Pictet-Spengler condensation of the desired 2-formylquinoline-5,8-diones with the required tryptophans followed by further needed transformations. Metabolism and toxicity studies demonstrated that the best substrates for NQO1 were also the most selectively toxic to NQO1-rich tumor cells compared to NQO1-deficient tumor cells. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1899 / 1909

页数：11

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