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Oxidative activation of leinamycin E1 triggers alkylation of guanine residues in double-stranded DNA

Abstract

It may be useful to develop prodrugs that are selectively activated by oxidative stress in cancer cells to release cell-killing reactive intermediates. However, relatively few chemical strategies exist for the activation of prodrugs by under conditions of oxidative stress. Here we provide evidence for a novel process in which oxidation of a thiol residue in the natural product leinamycin E1 by H2O2 and other byproducts of cellular oxidative stress initiates generation of an episulfonium ion that selectively alkylates guanine residues in duplex DNA.

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Publication details

The article was accepted on 01 Dec 2017 and first published on 05 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC08482J
Citation: Chem. Commun., 2017, Accepted Manuscript
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    Oxidative activation of leinamycin E1 triggers alkylation of guanine residues in double-stranded DNA

    M. Imani-Nejad, D. Yang, B. Shen and K. Gates, Chem. Commun., 2017, Accepted Manuscript , DOI: 10.1039/C7CC08482J

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