Published in
Royal Society of Chemistry, Chemical Communications, 89(50), p. 13729-13731
DOI: 10.1039/c4cc05657d
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Fragmentation of the quinoxaline N-oxide bond to the ˙OH radical upon one-electron bioreduction
Journal article published in 2014 by
Pooja Yadav,
Andrew J. Marshall,
Jóhannes Reynisson,
William A. Denny,
Michael P. Hay 
,
Robert F. Anderson
,
Robert F. Anderson
This paper was not found in any repository, but could be made available legally by the author.
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Abstract
The •OH radical is released from 3-trifluoromethyl-quinoxaline 1,4-dioxides upon one-electron reduction by cytochrome P450 oxidoreductase. This process effectively competes with back oxidation of the intermediate radical anion by oxygen and underlies the increased aerobic cytotoxicity of such compounds compared to that seen for the related clinical bioreductive benzotriazine drug, tirapazamine.