Issue 16, 2015

Maleimide-based acyclic enediyne for efficient DNA-cleavage and tumor cell suppression

Abstract

A pH-sensitive acyclic enediyne (1) was synthesized for efficient DNA-cleavage and tumor cell suppression. Unlike other acyclic enediynes, this novel enediyne transforms into a highly reactive enediyne (2) in an acidic environment only, which undergoes Bergman cyclization spontaneously at ambient temperature. An EPR study on the enediyne 2 confirmed the generation of free radicals through Bergman cyclization. The activated enediyne induced DNA-cleavage and exhibited cytotoxicity towards various tumor cells under the action of diradicals arising from spontaneous Bergman cyclization at physiological temperature. These findings suggest a novel strategy of anticancer drug design, where the activation of the silent compound takes place under the acidic environment inside the tumor cells.

Graphical abstract: Maleimide-based acyclic enediyne for efficient DNA-cleavage and tumor cell suppression

Supplementary files

Article information

Article type
Paper
Submitted
09 Dec 2014
Accepted
17 Feb 2015
First published
17 Feb 2015

J. Mater. Chem. B, 2015,3, 3195-3200

Maleimide-based acyclic enediyne for efficient DNA-cleavage and tumor cell suppression

D. Song, S. Sun, Y. Tian, S. Huang, Y. Ding, Y. Yuan and A. Hu, J. Mater. Chem. B, 2015, 3, 3195 DOI: 10.1039/C4TB02018A

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