Journal
FREE RADICAL BIOLOGY AND MEDICINE
Volume 63, Issue -, Pages 459-466Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.freeradbiomed.2013.05.008
Keywords
Halogenated quinones; 13-Hydroperoxy-9,11-octadecadienoic acid; ESR spin trapping; Lipid alkyl radicals; 4-Hydroxy-2-nonenal; Free radicals
Funding
- Project 973 [2008CB418106]
- Hundred-Talent Project, CAS
- NSF China Outstanding Youth Award [20925724]
- NSFC [21237005, 21207150, 21207139, 21077058, 21321004, 20921063]
- NIH [ES11497, RR01008, ES00210]
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Halogenated quinones are a class of carcinogenic intermediates and newly identified chlorination disinfection by-products in drinking water. 13-Hydroperoxy-9,11-octadecadienoic acid (13-HPODE) is the most extensively studied endogenous lipid hydroperoxide. Although it is well known that the decomposition of 13-HPODE can be catalyzed by transition metal ions, it is not clear whether halogenated quinones could enhance its decomposition independent of metal ions and, if so, what the unique characteristics and similarities are. Here we show that 2,5-dichloro-1,4-benzoquinone (DCBQ) could markedly enhance the decomposition of 13-HPODE and formation of reactive lipid alkyl radicals such as pentyl and 7-carboxyheptyl radicals, and the genotoxic 4-hydroxy-2-nonenal (HNE), through the complementary application of ESR spin trapping, HPLC MS, and GC MS methods. Interestingly, two chloroquinone-lipid alkoxyl conjugates were also detected and identified from the reaction between DCBQ and 13-HPODE. Analogous results were observed with other halogenated quinones. This represents the first report that halogenated quinoid carcinogens can enhance the decomposition of the endogenous lipid hydroperoxide 13-HPODE and formation of reactive lipid alkyl radicals and genotoxic HNE via a novel metal-independent nucleophilic substitution coupled with homolytic decomposition mechanism, which may partly explain their potential genotoxicity and carcinogenicity. (C) 2013 Elsevier Inc. All rights reserved.
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