Enantioselective endocrine-disrupting effects of the phenylpyrazole chiral insecticides in vitro and in silico.,Chemosphere

当前位置： X-MOL 学术 › Chemosphere › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Enantioselective endocrine-disrupting effects of the phenylpyrazole chiral insecticides in vitro and in silico.
Chemosphere ( IF 8.1 ) Pub Date : 2020-03-20 , DOI: 10.1016/j.chemosphere.2020.126572
Kunming Hu ₁ , Liangliang Zhou ₁ , Yingying Gao ₁ , Qi Lai ₁ , Haiyan Shi ₁ , Minghua Wang ₁

Affiliation

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.

中文翻译：

苯吡唑手性杀虫剂在体外和计算机上的对映选择性内分泌干扰作用。

苯基吡唑手性杀虫剂，包括广泛使用的氟虫腈，乙腈和氟虫腈，由于其环境毒性而引起了全世界的关注。但是，到目前为止，只有很少的研究关注其潜在的内分泌干扰作用（EDE）。在这项研究中，我们研究了由氟虫腈，乙腈和氟虫腈对映异构体在体外和计算机模拟中引起的内分泌激素紊乱。荧光素酶报告基因测定的结果表明，氟虫腈，乙腈或氟虫腈的对映异构体显示出立体选择性内分泌干扰作用。S-（-）-乙腈和S-（-）-氟乙丙啶具有抗甲状腺疾病的作用，而R-（-）-氟苯腈，R-（+）-乙丙啶和R-（+）-氟乙丙啶显示出抗雌激素作用疾病的影响。分子动力学模拟的结果表明，发生的EDE可能部分归因于对映选择性特异性受体结合亲和力。这也表明范德华相互作用在结合过程中起着重要作用。该研究为分子级手性苯基吡唑类农药的EDE中的对映选择性的解释提供了有益的信息。

更新日期：2020-03-20

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南