title: Enantioselective induction of estrogen-responsive gene expression by permethrin enantiomers in embryo-larval zebrafish.
abstract: Enantioselectivity in the separation, toxicology, biodegradation and estrogenic activity of chiral pesticides has become a groundbreaking topic recently. In this study, real-time, quantitative polymerase chain reaction was adapted to investigate the induction of estrogen-responsive gene expression in embryo-larval zebrafish after 7 d of exposure to permethrin (PM) enantiomers. The PM enantiomers were completely separated by a chiral HPLC column. The in vivo study found that a 7 d exposure to 250 ng L(-1) PM racemate and its enantiomers was sufficient to stimulate vtg1, esralpha and cyp19b expression, while 1000 ng L(-1) exposure significantly induced gene expression in a pattern similar to that of the control (50 ng L(-1) E2), except for vtg2. Significant differences were detected between the enantiomers in the induction of estrogen-responsive gene expression. At the exposure level of 1000 ng L(-1), the vtg1, esralpha and cyp19b responses to the (-)-trans enantiomer were about 3.2-, 1.8- and 1.5-fold higher, respectively, than those in the group treated with (+)-trans enantiomer (p < 0.05). In the two cis-enantiomer treatment groups, (+)-cis increased the mRNA level of the cyp19b gene about 1.5-fold higher than the (-)-cis-enantiomer did. Of the four enantiomers, the (-)-trans enantiomer showed the greatest estrogenic activity. The results strongly indicate the occurrence of significant enantioselectivity in estrogenic activity of PM enantiomers exposed to embryo-larval zebrafish. These findings add to a growing body of evidence concerning enantioselectivity in the toxicity, endocrine-disrupting activity, and environmental biodegradation of chiral pesticides.
authors.affiliation: College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310032, China.
authors.forename: Yuanxiang
authors.initials: Y
authors.lastname: Jin
authors.forename: Rujia
authors.initials: R
authors.lastname: Chen
authors.forename: Liwei
authors.initials: L
authors.lastname: Sun
authors.forename: Wanyuan
authors.initials: W
authors.lastname: Wang
authors.forename: Lin
authors.initials: L
authors.lastname: Zhou
authors.forename: Weiping
authors.initials: W
authors.lastname: Liu
authors.forename: Zhengwei
authors.initials: Z
authors.lastname: Fu
mesh_terms: D000818:Animals; D001141:Aromatase / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D017931:DNA Primers / Q000235:genetics; D004305:Dose-Response Relationship, Drug; D004967:Estrogens / Q000378:metabolism*; D005786:Gene Expression Regulation / Q000187:drug effects*; D007306:Insecticides / Q000737:chemistry / Q000633:toxicity*; D026023:Permethrin / Q000737:chemistry / Q000633:toxicity*; D020133:Reverse Transcriptase Polymerase Chain Reaction; D013237:Stereoisomerism; D015027:Zebrafish / Q000378:metabolism*; D029961:Zebrafish Proteins / Q000378:metabolism
chemical_list: D017931:DNA Primers; D004967:Estrogens; D007306:Insecticides; D029961:Zebrafish Proteins; D026023:Permethrin; D001141:Aromatase; C440729:Cyp19a1a protein, zebrafish