The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product

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• 作者：Santhosh Sivaramakrishnan^a ; Leonid Breydo^a ; Daekyu Sun^c ; Kent S. Gates^a ; ^b ; ^{gatesk@missouri.edu}
• 关键词：DNA cleavage ; DNA damage
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2012
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：1 June, 2012
• 卷：22
• 期：11
• 页码：3791-3794
• 文件大小：320 K

摘要

Reaction of cellular thiols with the 1,2-dithiolan-3-one 1-oxide moiety of leinamycin triggers the generation of DNA-damaging reactive intermediates. Studies with small, synthetic analogues of leinamycin reveal that the macrocyclic portion of the natural product imparts remarkable hydrolytic stability to the 1,2-dithiolan-3-one 1-oxide heterocycle without substantially compromising its thiol-sensing property.