Unexpected transformation of dissolved phenols to toxic dicarbonyls by hydroxyl radicals and UV light

Proceedings of the National Academy of Sciences of the United States of America
Carsten PrasseDavid L Sedlak

Abstract

Water treatment systems frequently use strong oxidants or UV light to degrade chemicals that pose human health risks. Unfortunately, these treatments can result in the unintended transformation of organic contaminants into toxic products. We report an unexpected reaction through which exposure of phenolic compounds to hydroxyl radicals (•OH) or UV light results in the formation of toxic α,β-unsaturated enedials and oxoenals. We show that these transformation products damage proteins by reacting with lysine and cysteine moieties. We demonstrate that phenolic compounds react with •OH produced by the increasingly popular UV/hydrogen peroxide (H2O2) water treatment process or UV light to form toxic enedials and oxoenals. In addition to raising concerns about potential health risks of oxidative water treatment, our findings suggest the potential for formation of these toxic compounds in sunlit surface waters, atmospheric water, and living cells. For the latter, our findings may be particularly relevant to efforts to understand cellular damage caused by in vivo production of reactive oxygen species. In particular, we demonstrate that exposure of the amino acid tyrosine to •OH yields an electrophilic enedial product that undergoes cro...Continue Reading

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Citations

Jun 5, 2020·Chemical Communications : Chem Comm·Guoyang ZhangShujuan Zhang
Oct 10, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Irina I Vlasova
Mar 22, 2019·Environmental Science and Pollution Research International·Jacqueline A Malvestiti, Renato F Dantas
Feb 11, 2021·Environmental Science & Technology·Emily L MarronDavid L Sedlak
Apr 17, 2020·Water Research·Xiujuan KongJingyun Fang
Nov 7, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Magdalena BlachnioMariia Galaburda
May 22, 2020·Journal of Agricultural and Food Chemistry·Zichen ZhaoMarianne N Lund
Nov 11, 2020·Environmental Science & Technology·David Ross HallHui Peng
Jan 7, 2020·Environmental Science & Technology·Carsten PrasseDavid L Sedlak
Jun 28, 2019·Environmental Science & Technology·Qing ZhangGuibin Jiang
Apr 20, 2018·Environmental Science & Technology·Urs von Gunten
Aug 25, 2020·Environmental Science & Technology·Emily L MarronDavid L Sedlak

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Methods Mentioned

BETA
fluorescence imaging

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