title: Enantioselectivity in estrogenicity of the organochlorine insecticide acetofenate in human trophoblast and MCF-7 cells.
abstract: Previous studies have showed that some chiral pesticides with estrogenic activity possess enantioselectivity in endocrine disruption. Despite the assessment of enantioselectivity in the estrogenic potential of chiral pesticides, which deserve particular attention, there has been limited research into their molecular mechanisms of human health risk. In this study, the role of enantioselectivity in the endocrine disruption and potential human maternal-fetal health risk of acetofenate (AF), an organochlorine insecticide, were investigated in both MCF-7 and JEG-3 cells. The two in vitro assays showing a clear enantioselectivity in the estrogenic activity with S-(+)-AF showed stronger effects than R-(-)-AF and rac-AF. Moreover, the racemate's estrogenicity was in between that of enantiomers. Our results also demonstrated that S-(+)-AF possesses the strongest potential effects in disruption of hormone secretion, maternal immune tolerance, and steroidogenesis in the trophoblast. The results suggest that assessment of the health risk of chiral contaminants should consider the role of enantioselectivity.
authors: College of Environmental Science and Engineering, Zhejiang Gongshang University, Hangzhou 310018, People's Republic of China.
authors: Fang
authors: F
authors: Chen
authors: Quan
authors: Q
authors: Zhang
authors: Cui
authors: C
authors: Wang
authors: Yingchong
authors: Y
authors: Lu
authors: Meirong
authors: M
authors: Zhao
mesh_terms: D001141:Aromatase / Q000235:genetics / Q000378:metabolism; D001681:Biological Assay; D001943:Breast Neoplasms / Q000235:genetics / Q000473:pathology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D052244:Endocrine Disruptors / Q000737:chemistry / Q000633:toxicity*; D004967:Estrogens / Q000737:chemistry / Q000633:toxicity*; D004980:Ethane / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D005260:Female; D005786:Gene Expression Regulation / Q000187:drug effects; D059951:HLA-G Antigens / Q000235:genetics / Q000378:metabolism; D006801:Humans; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry / Q000633:toxicity*; D007306:Insecticides / Q000737:chemistry / Q000633:toxicity*; D007536:Isomerism; D011375:Progesterone Reductase / Q000235:genetics / Q000378:metabolism; D012333:RNA, Messenger / Q000378:metabolism; D011980:Receptors, Progesterone / Q000187:drug effects / Q000235:genetics / Q000378:metabolism; D018570:Risk Assessment; D013997:Time Factors; D018675:Toxicity Tests; D014327:Trophoblasts / Q000187:drug effects* / Q000473:pathology
chemical_list: C530171:2,2,2,-trichloro-1-(3,4-dichlorophenyl)-ethylacetate; D052244:Endocrine Disruptors; D004967:Estrogens; D059951:HLA-G Antigens; D006843:Hydrocarbons, Chlorinated; D007306:Insecticides; D012333:RNA, Messenger; D011980:Receptors, Progesterone; C533068:3 beta-hydroxysteroid dehydrogenase type II; D011375:Progesterone Reductase; D001141:Aromatase; D004980:Ethane