5-alkynyl-2′-deoxyuridines:: Chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells

被引：48
|
作者：
Meneni, Srinivasarao
Ott, Ingo
Sergeant, Craig D.
Sniady, Adam
Gust, Ronald
Dembinski, Roman
机构：
[1] Oakland Univ, Dept Chem, Rochester, MI 48309 USA
[2] Free Univ Berlin, Inst Pharm, D-14195 Berlin, Germany
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 08期
关键词：
nucleosides; alkynes; 5-alkynyl-2 '-deoxyuridines; antitumor chemotherapy; anticancer; anti-proliferative agents; human breast cancer cells; MCF-7; MDA-MB-231;
D O I：
10.1016/j.bmc.2007.01.048
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：
Starting with 5-iodo-2'-deoxyuridine, a series of 5-alkynyl-2'-deoxyuridines (with n-propyl, cyclopropyl, 1-hydroxycyclohexyl, p-tolyl, p-tert-butylphenyl, p-pentylphenyl, and trimethylsilyl alkyne substituents) have been synthesized via the palladium-catalyzed (Sonogashira) coupling reaction followed by a simplified isolation protocol (76-94% yield). The cytotoxic activity of modified nucleosides against MCF-7 and MDA-MB-231 human breast cancer cells has been determined in vitro. 5-Ethynyl-2'-deoxyuridine, the only nucleoside in the series containing a terminal acetylene, is the most potent inhibitor with IC50 (mu M) 0.4 +/- 0.3 for MCF-7 and 4.4 +/- 0.4 for MDA-MB-231. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3082 / 3088
页数：7
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