Characterisation of radicals formed by the triazine 1,4-dioxide hypoxia-activated prodrug, SN30000

Robert F. Anderson, Pooja Yadav, Deepa Patel, Jóhannes Reynisson, Smitha R. Tipparaju, Christopher P. Guise, Adam V. Patterson, William A. Denny, Andrej Maroz, Sujata S. Shinde, Michael P. Hay

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The radical species underlying the activity of the bioreductive anticancer prodrug, SN30000, have been identified by electron paramagnetic resonance and pulse radiolysis techniques. Spin-trapping experiments indicate both an aryl-type radical and an oxidising radical, trapped as a carbon-centred radical, are formed from the protonated radical anion of SN30000. The carbon-centred radical, produced upon the one-electron oxidation of the 2-electron reduced metabolite of SN30000, oxidises 2-deoxyribose, a model for the site of damage on DNA which leads to double strand breaks. Calculations using density functional theory support the assignments made.

Original languageEnglish
Pages (from-to)3386-3392
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number21
DOIs
Publication statusPublished - 7 Jun 2014
Externally publishedYes

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