Emerging Disinfection Byproducts, Halobenzoquinones: Effects of Isomeric Structure and Halogen Substitution on Cytotoxicity, Formation of Reactive Oxygen Species, and Genotoxicity

Environmental Science & Technology
Jinhua LiXing-Fang Li

Abstract

Halobenzoquinones (HBQs) are a structurally diverse class of water disinfection byproducts. Here, we report a systematic study on the effects of isomeric structure and the type and number of halogen substitutions of HBQs on their cytotoxicity, formation of reactive oxygen species (ROS), and genotoxicity. Dynamic responses and IC50 histograms were obtained using real-time cell analysis, clearly ranking the cytotoxicity of the HBQs in Chinese hamster ovary (CHO-K1) cells. Strong isomeric structure effects were shown with 2,5-HBQ isomers inducing greater cytotoxicity than their corresponding 2,6-HBQ isomers (P < 0.05). HBQ-halogen substitution groups also influence cytotoxicity, as cytotoxicity increases across the dihalogenated HBQs: iodo- > bromo- > chloro-HBQs (P < 0.05). Determination of HBQ-induced ROS further supports isomeric structure and halogen substitution effects. HBQ-induced genotoxicity was shown as increased levels of 8-hydroxy-2'-deoxyguanosine and p53 protein. Pearson correlation analysis of the HBQ toxicity measurements with their physicochemical parameters demonstrates that dipole moment and the lowest unoccupied molecular orbital energy are two major structural influences on toxicity (r = -0.721 or -0.766, P < ...Continue Reading

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Citations

Dec 30, 2016·Journal of Chemical Information and Modeling·Florbela PereiraJoao Aires-de-Sousa
May 7, 2019·Journal of Toxicology·Brooke McMinnChristie M Sayes
Jan 31, 2021·The Science of the Total Environment·Huan WuXiao Wei
Jul 13, 2019·Ecotoxicology and Environmental Safety·Yixing FengBing Shao
Aug 21, 2018·Environmental Science & Technology·Chang WangXing-Fang Li
Mar 24, 2020·Chemical Research in Toxicology·Dayong TianXing-Fang Li
Jan 8, 2020·Environmental Science & Technology·Jingyi JiangXiangru Zhang

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