title: Estrogenicity of pyrethroid insecticide metabolites.
abstract: There is concern that insecticides are able to mimic the action of 17beta-estradiol by interaction with the human estrogen receptor. Pyrethroids are commonly used insecticides and several have been assessed for potential endocrine disrupting activity by various methods. It has been noted that some metabolites of pyrethroids, in particular, permethrin and cypermethrin, have chemical structures that are more likely to interact with the cellular estrogen receptor than the parent pyrethroid. For this study permethrin and cypermethrin metabolites 3-(4-hydroxy-3-phenoxy)benzyl alcohol, 3-(4-hydroxy-3-phenoxy)benzoic acid, and N-3-(phenoxybenzoyl)glycine were synthesised, and together with the commercially available 3-phenoxybenzyl alcohol, 3-phenoxybenzaldehyde, and 3-phenoxybenzoic acid, were studied in a recombinant yeast assay expressing human estrogen receptors (YES). Three metabolites, 3-phenoxybenzyl alcohol, 3-(4-hydroxy-3-phenoxy)benzyl alcohol, and 3-phenoxybenzaldehyde, showed estrogenic activity of approximately 10(5) less than that of 17beta-estradiol. No activity was observed in the yeast assay for 3-phenoxybenzoic acid, 3-(4-hydroxy-3-phenoxy)benzoic acid, and N-3-(phenoxybenzoyl)glycine. The results from this study show that pyrethroid metabolites are capable of interacting with the human estrogen receptor, and so might present a risk to human health and environmental well being. The impact would be expected to be small, but still add to the overall environmental xenoestrogen load.
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.
authors.forename: Anna R
authors.initials: AR
authors.lastname: McCarthy
authors.forename: Barbara M
authors.initials: BM
authors.lastname: Thomson
authors.forename: Ian C
authors.initials: IC
authors.lastname: Shaw
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Abell
mesh_terms: D001681:Biological Assay; D004785:Environmental Pollutants / Q000378:metabolism; D047628:Estrogen Receptor alpha / Q000378:metabolism*; D004968:Estrogens, Non-Steroidal / Q000378:metabolism*; D007306:Insecticides / Q000378:metabolism; D026023:Permethrin / Q000378:metabolism*; D010573:Pesticide Residues / Q000378:metabolism*; D011722:Pyrethrins / Q000378:metabolism*; D012441:Saccharomyces cerevisiae / Q000378:metabolism
chemical_list: D004785:Environmental Pollutants; D047628:Estrogen Receptor alpha; D004968:Estrogens, Non-Steroidal; D007306:Insecticides; D010573:Pesticide Residues; D011722:Pyrethrins; C017160:cypermethrin; D026023:Permethrin