Potential Chemopreventive Agents Based on the Structure of the Lead Compound 2-Bromo-1-hydroxyphenazine, Isolated from Streptomyces Species, Strain CNS284

被引：57

作者：

Conda-Sheridan, Martin ^{[1
,2
]}

Marler, Laura ^{[3
]}

Park, Eun-Jung ^{[3
]}

Kondratyuk, Tamara P. ^{[3
]}

Jermihov, Katherine ^{[2
,4
,5
]}

Mesecar, Andrew D. ^{[2
,4
,5
]}

Pezzuto, John M. ^{[3
]}

Asolkar, Ratnakar N. ^{[6
]}

Fenical, William ^{[6
]}

Cushman, Mark ^{[1
,2
]}

机构：

[1] Purdue Univ, Dept Med Chem & Mol Pharmacol, Coll Pharm, W Lafayette, IN 47907 USA

[2] Purdue Univ, Ctr Canc Res, W Lafayette, IN 47907 USA

[3] Univ Hawaii, Coll Pharm, Hilo, HI 96720 USA

[4] Purdue Univ, Ctr Pharmaceut Biotechnol, W Lafayette, IN 47907 USA

[5] Purdue Univ, Dept Med Chem & Pharmacognosy, Dept Biol Sci, W Lafayette, IN 47907 USA

[6] Univ Calif San Diego, Scripps Inst Oceanog, La Jolla, CA 92037 USA

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 53卷 / 24期

基金：

美国国家卫生研究院;

关键词：

PHASE-II ENZYME; NF-KAPPA-B; QUINONE REDUCTASE; CANCER CHEMOPREVENTION; METABOLIZING-ENZYMES; MOLECULAR TARGETS; NATURAL-PRODUCTS; INDUCTION; PHENAZINE; INHIBITORS;

D O I：

10.1021/jm1011066

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The isolation of 2-bromo-1-hydroxyphenazine from a marine Streptomyces species, strain CNS284, and its activity against NF-kappa B, suggested that a short and flexible route for the synthesis of this metabolite and a variety of phenazine analogues should be developed. Numerous phenazines were subsequently prepared and evaluated as inducers of quinone reductase I (QR1) and inhibitors of quinone reductase 2 (QR2), NF-kappa B, and inducible nitric oxide synthase (iNOS). Several of the active phenazine derivatives displayed IC50 values vs QR1 induction and QR2 inhibition in the nanomolar range, suggesting that they may find utility as cancer chemopreventive agents.

引用

页码：8688 / 8699

页数：12

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