Pseudoverticin, a novel benzoquinone-derived ansamycin antibiotic obtained as new cell cycle inhibitor from Streptomyces pseudoverticillus YN17707

被引：5
作者：
Cui, Cheng-Bin
Han, Bing
Cai, Bing
Wang, Hao
机构：
[1] Beijing Inst Pharmacol & Toxicol, Beijing 100850, Peoples R China
[2] Beijing Inst Biomed, Beijing 100091, Peoples R China
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 28期
基金：
中国国家自然科学基金;
关键词：
Pseudoverticin; geldanamycin; Streptomyces pseudoverticillus; ansamycin antibiotic; cell cycle inhibitor; structure;
D O I：
10.1016/j.tetlet.2007.05.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pseudoverticin (1), a novel benzoquinone-derived ansamycin antibiotic showing cell cycle inhibitory activity, was isolated from the fermentation broth of Streptomyces pseudoverticillus YN17707 together with the known ansamycin antibiotic geldanamycin (2) through a bioassay-guided separation procedure. The structure of 1 was elucidated by spectroscopic methods, being characterized by an ansa bridge the same as that in 2 and a novel benzoquinone-derived moiety. Pseudoverticin (1) arrested the cell cycle of tsFT210 cells at the G0/G1 phase with the MIC value of 2.5 mu M. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4839 / 4843
页数：5
相关论文
共 72 条
[11]   GELDANAMYCIN, A NEW ANTIBIOTIC [J].
DEBOER, C ;
MEULMAN, PA ;
WNUK, RJ ;
PETERSON, DH .
JOURNAL OF ANTIBIOTICS, 1970, 23 (09) :442-&
[12]   Toxoplasma gondii Hsp90 is a potential drug target whose expression and subcellular localization are developmentally regulated [J].
Echeverria, PC ;
Matrajt, M ;
Harb, OS ;
Zappia, MP ;
Costas, MA ;
Roos, DS ;
Dubremetz, JF ;
Angel, SO .
JOURNAL OF MOLECULAR BIOLOGY, 2005, 350 (04) :723-734
[13]   Pharmacokinetics and pharmacodynamics of 17-demethoxy 17-[[(2-dimethylamino)ethyl]amino]geldanamycin (17DMAG, NSC 707545) in C.B-17 SCID mice bearing MDA-MB-231 human breast cancer xenografts [J].
Eiseman, JL ;
Lan, J ;
Lagattuta, TF ;
Hamburger, DR ;
Joseph, E ;
Covey, JM ;
Egorin, MJ .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 2005, 55 (01) :21-32
[14]   Hsp90 inhibitor geldanamycin increases hsp70 mRNA stabilisation but fails to activate HSF1 in cells exposed to hydrostatic pressure [J].
Elo, MA ;
Kaarniranta, K ;
Helminen, HJ ;
Lammi, MJ .
BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR CELL RESEARCH, 2005, 1743 (1-2) :115-119
[15]   HERBIMYCIN-A - AN ANSAMYCIN ANTIBIOTIC - X-RAY CRYSTAL-STRUCTURE [J].
FURUSAKI, A ;
MATSUMOTO, T ;
NAKAGAWA, A ;
OMURA, S .
JOURNAL OF ANTIBIOTICS, 1980, 33 (07) :781-782
[16]   17-Allyamino-17-demethoxygeldanamycin and 17-NN-dimethyl ethylene diamine-geldanamycin have cytotoxic activity against multiple gynecologic cancer cell types [J].
Gossett, DR ;
Bradley, MS ;
Jin, XH ;
Lin, JY .
GYNECOLOGIC ONCOLOGY, 2005, 96 (02) :381-388
[17]   BIOSYNTHETIC ORIGIN OF C2 UNITS OF GELDANAMYCIN AND DISTRIBUTION OF LABEL FROM D-[6-13C]GLUCOSE [J].
HABER, A ;
JOHNSON, RD ;
RINEHART, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) :3541-3544
[18]  
Han B, 2005, CHINESE CHEM LETT, V16, P471
[19]  
[Han Bing 韩冰], 2004, [中国药物化学杂志, Chinese Journal of Medicinal Chemistry], V14, P370
[20]   ZHD-0501, a novel naturally occurring staurosporine analog from Actinomadura sp. 007 [J].
Han, XX ;
Cui, CB ;
Gu, QQ ;
Zhu, WM ;
Liu, HB ;
Gu, JY ;
Osada, H .
TETRAHEDRON LETTERS, 2005, 46 (36) :6137-6140
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