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

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...

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Bibliographic Details
Published in:Environmental science & technology 2021-07, Vol.55 (13), p.9087-9096
Main Authors: Ji, Chenyang, Tanabe, Philip, Shi, Qingyang, Qian, Le, McGruer, Victoria, Magnuson, Jason T, Wang, Xinru, Gan, Jay, Gadepalli, Rama S, Rimoldi, John, Schlenk, Daniel
Format: Article
Language:English
Subjects:
Age
Animals
Conjugation
Cytochrome
Cytochrome P450
Cytochromes P450
Danio rerio
Ecotoxicology and Public Health
Embryos
Enantiomers
Estrogenic activity
Insecticides
Ketoconazole
Liver
Metabolism
Metabolites
Oryzias latipes
Oxidation
Pyrethroids
Risk assessment
Surface water
Wildlife
Xenoestrogens
Zebrafish
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Summary: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 β-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.
ISSN:0013-936X
1520-5851
DOI:10.1021/acs.est.1c01663