Stage Dependent Enantioselective Metabolism of Bifenthrin in Embryos of Zebrafish (Danio rerio) and Japanese Medaka (Oryzias latipes)

文献类型： 外文期刊

第一作者： Ji, Chenyang

作者： Ji, Chenyang;Tanabe, Philip;Shi, Qingyang;Qian, Le;McGruer, Victoria;Magnuson, Jason T.;Wang, Xinru;Gan, Jay;Schlenk, Daniel;Qian, Le;Wang, Xinru;Gadepalli, Rama S.;Rimoldi, John

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关键词： bifenthrin; 4-hydroxybifenthrin; enantioselective metabolism; zebrafish; Japanese medaka

期刊名称：ENVIRONMENTAL SCIENCE & TECHNOLOGY （ 影响因子：9.028； 五年影响因子：9.922 ）

ISSN： 0013-936X

年卷期： 2021 年 55 卷 13 期

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收录情况： SCI

摘要： Bifenthrin (BF) is a widely used pyrethroid that has been frequently detected in surface waters. Previous studies indicated that BF had antiestrogenic activity in zebrafish embryos but estrogenic activity in posthatch fish. To determine whether age-related differences in metabolism contribute to the endocrine effects in developing fish, embryos from zebrafish and Japanese medaka were exposed to BF before and after liver development. Since the commercial mixture of BF is an isomer-enriched product containing two enantiomers (1R-cis-BF and 1S-cis-BF), enantioselective metabolism was also evaluated. The estrogenic metabolite, 4-hydroxybifenthrin (4-OH-BF) was identified in zebrafish embryos, and formation was higher in animals after liver development (> 48 hpf). Treatments with beta-glucuronidase indicated that 4-OH-BF underwent conjugation in embryos. Formation was reduced by cotreatment of the cytochrome P450 (CYP450) inhibitor, ketoconazole. Formation of 4-OH-BF was greater when treated with 1R-cis-BF compared to the S-enantiomer. However, metabolites were not observed in medaka embryos. These data indicate enantioselective oxidation of BF to an estrogenic metabolite occurs in zebrafish embryos and, since it is increased after liver development, may partially explain estrogenic activity observed in older animals. The lack of activity in medaka suggests species-specific effects with BF metabolism and may influence risk assessment strategies in wildlife.

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