Issue 21, 2014

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Jan 2014
Accepted
09 Apr 2014
First published
10 Apr 2014

Org. Biomol. Chem., 2014,12, 3386-3392

Author version available

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

R. F. Anderson, P. Yadav, D. Patel, J. Reynisson, S. R. Tipparaju, C. P. Guise, A. V. Patterson, W. A. Denny, A. Maroz, S. S. Shinde and M. P. Hay, Org. Biomol. Chem., 2014, 12, 3386 DOI: 10.1039/C4OB00236A

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