Enantioselective endocrine-disrupting effects of the phenylpyrazole chiral insecticides in vitro and in silico. (August 2020)

• Record Type: Journal Article
• Authors: Hu, Kunming; Zhou, Liangliang; Gao, Yingying; Lai, Qi; Shi, Haiyan; Wang, Minghua
• Is Part Of: Chemosphere. Volume 252(2020)
• Publication Date: 2020-08
• Subjects: Phenylpyrazole insecticides -- Endocrine-disrupting effects -- Molecular dynamics -- Reporter gene; Pollution -- Periodicals; Pollution -- Physiological effect -- Periodicals; Environmental sciences -- Periodicals; Atmospheric chemistry -- Periodicals; 551.511
• DOI: 10.1016/j.chemosphere.2020.126572
• Languages: English
• ISSNs: 0045-6535

Abstract

Abstract: The phenylpyrazole chiral insecticides, including the widely used fipronil, ethiprole, and flufiprole, have generated a worldwide interest due to their environmental toxicity. However, up to now, only few studies focused on their their potential endocrine-disrupting effects (EDEs). In this study, we investigated the endocrine hormonal disorder caused by the fipronil, ethiprole, and flufiprole enantiomers in vitro and in silico approach. Results of the luciferase reporter assay indicated that the enantiomers of fipronil, ethiprole, or flufiprole have shown stereoselective endocrine-disrupting effects. S- (−)-ethiprole and S- (−)-flufiprole have anti-thyroidal disorder effects whereas R- (−)-fipronil, R- (+)-ethiprole, and R- (+)-flufiprole showed anti-estrogenic disorder effects. The results of the molecular dynamics simulations revealed that the happened EDEs could be partially attributed to the enantioselective specific receptor binding affinities. It also suggested that Vander Waals interactions plays an important role in the binding procedure. This study could provide helpful information for the explanation of enantioselectivity in the EDEs of chiral phenylpyrazole pesticides at the molecular level. Graphical abstract: Image 1 Highlights: The phenylpyrazole insecticides exerted different endocrine-disrupting effects (EDEs). Dual-luciferase reporter gene assays rapidly screened the endocrine disruptors. Molecular dynamics simulations revealed the mechanism of stereoselectivity. Our findings provide constructive guidance for the safe use of chiral pesticides.