AI Article Synopsis
- Haloquinones (XQs) are identified as carcinogenic compounds derived from environmental pollutants and disinfection byproducts in drinking water.
- The study reveals that XQs can cause oxidative damage to DNA through mechanisms involving hydroxyl radicals and quinone enoxy/ketoxy radicals, independent of metal ions.
- Research shows that exposure to XQs leads to DNA modifications and breaks, potentially increasing mutagenic effects in living cells and highlighting the genotoxic risks associated with these compounds.
Article Abstract
Haloquinones (XQs) are a group of carcinogenic intermediates of the haloaromatic environmental pollutants and newly identified chlorination disinfection byproducts (DBPs) in drinking water. The highly reactive hydroxyl radicals/alkoxyl radicals and quinone enoxy/ketoxy radicals were found to arise in XQs and HO or organic hydroperoxides system, independent of transition-metal ions. However, it was not clear whether these haloquinoid carcinogens and hydroperoxides can cause oxidative DNA damage and modifications, and if so, what are the underlying molecular mechanisms. We found that 8-oxodeoxyguanosine (8-oxodG), DNA strand breaks, and three methyl oxidation products could arise when DNA was treated with tetrachloro-1,4-benzoquinone and HO via a metal-independent and intercalation-enhanced oxidation mechanism. Similar effects were observed with other XQs, which are generally more efficient than the typical Fenton system. We further extended our studies from isolated DNA to genomic DNA in living cells. We also found that potent oxidation of DNA to the more mutagenic imidazolone dIz could be induced by XQs and organic hydroperoxides such as -butylhydroperoxide or the physiologically relevant hydroperoxide 13S-hydroperoxy-9Z,11E-octadecadienoic acid via an unprecedented quinone-enoxy radical-mediated mechanism. These findings should provide new perspectives to explain the potential genotoxicity, mutagenesis, and carcinogenicity for the ubiquitous haloquinoid carcinogenic intermediates and DBPs.
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| http://dx.doi.org/10.1021/acs.chemrestox.1c00158 | DOI Listing |
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