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Issue 16, 2015
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Maleimide-based acyclic enediyne for efficient DNA-cleavage and tumor cell suppression

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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

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Publication details

The article was received on 09 Dec 2014, accepted on 17 Feb 2015 and first published on 17 Feb 2015


Article type: Paper
DOI: 10.1039/C4TB02018A
Citation: J. Mater. Chem. B, 2015,3, 3195-3200
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    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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