Potent Oxidation of DNA by Haloquinoid Disinfection Byproducts to the More Mutagenic Imidazolone dlz via an Unprecedented Haloquinone-Enoxy Radical-Mediated Mechanism
文献类型：期刊论文
| 作者 | Shao, Jie; Huang, Chun-Hua; Shao, Bo; Qin, Li; Xu, Dan; Li, Feng ; Qu, Na; Xie, Lin-Na; Kalyanaraman, Balaraman; Zhu, Ben-Zhan
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| 刊名 | ENVIRONMENTAL SCIENCE & TECHNOLOGY
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| 出版日期 | 2020-05-19 |
| 卷号 | 54期号:10页码:6244-6253 |
| ISSN号 | 0013-936X |
| 英文摘要 | Halogenated quinones are a class of carcinogenic intermediates and newly identified chlorination disinfection byproducts in drinking water. We found recently that halogenated quinones could enhance the decomposition of hydroperoxides independent of transition-metal ions and formation of the novel quinone enoxy/ketoxy radicals. Here, we show that the major oxidation product was 2-amino-5-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one (dlz) when the nucleoside 2'-deoxyguanosine (dG) was treated with tetrachloro-1,4-benzoquinone (TCBQ) and t-butyl hydroperoxide (t-BuOOH). The formation of dlz was markedly inhibited by typical radical spin-trapping agents. Interestingly and unexpectedly, we found that the generated quinone enoxy radical played a critical role in dlz formation. Using [N-15(5)]-8-oxodG, dlz was found to be produced either directly from dG or through the transient formation of 8-oxodG. Based on these data, we proposed that the production of dlz might be through an unusual haloquinone-enoxy radical- mediated mechanism. Analogous results were observed in the oxidation of ctDNA by TCBQ/t-BuOOH and when t-BuOOH was substituted by the endogenously generated physiologically relevant hydroperoxide 13S-hydroperoxy-9Z,11E-octadecadienoic acid. This is the first report that halogenated quinoid carcinogens and hydroperoxides can induce potent oxidation of dG to the more mutagenic product dlz via an unprecedented quinone-enoxy radical-mediated mechanism, which may partly explain their potential carcinogenicity. |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/44781]  |
| 专题 | 生态环境研究中心_环境化学与生态毒理学国家重点实验室 |
| 推荐引用方式 GB/T 7714 | Shao, Jie,Huang, Chun-Hua,Shao, Bo,et al. Potent Oxidation of DNA by Haloquinoid Disinfection Byproducts to the More Mutagenic Imidazolone dlz via an Unprecedented Haloquinone-Enoxy Radical-Mediated Mechanism[J]. ENVIRONMENTAL SCIENCE & TECHNOLOGY,2020,54(10):6244-6253. |
| APA | Shao, Jie.,Huang, Chun-Hua.,Shao, Bo.,Qin, Li.,Xu, Dan.,...&Zhu, Ben-Zhan.(2020).Potent Oxidation of DNA by Haloquinoid Disinfection Byproducts to the More Mutagenic Imidazolone dlz via an Unprecedented Haloquinone-Enoxy Radical-Mediated Mechanism.ENVIRONMENTAL SCIENCE & TECHNOLOGY,54(10),6244-6253. |
| MLA | Shao, Jie,et al."Potent Oxidation of DNA by Haloquinoid Disinfection Byproducts to the More Mutagenic Imidazolone dlz via an Unprecedented Haloquinone-Enoxy Radical-Mediated Mechanism".ENVIRONMENTAL SCIENCE & TECHNOLOGY 54.10(2020):6244-6253. |
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来源：生态环境研究中心
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