Disruption of the Hormonal Network and the Enantioselectivity of Bifenthrin in Trophoblast: Maternal–Fetal Health Risk of Chiral Pesticides

Abstract

Endocrine-disrupting chemicals (EDCs) can interfere with normal hormone signaling to increase health risks to the maternal-fetal system, yet few studies have been conducted on the currently used chiral EDCs. This work tested the hypothesis that pyrethroids could enantioselectively interfere with trophoblast cells. Cell viability, hormone secretion, and steroidogenesis gene expression of a widely used pyrethroid, bifenthrin (BF), were evaluated in vitro, and the interactions of BF enantiomers with estrogen receptor (ER) were predicted. At low or noncytotoxic concentrations, both progesterone and human chorionic gonadotropin secretion were induced. The expression levels of progesterone receptor and human leukocyte antigen G genes were significantly stimulated. The key regulators of the hormonal cascade, GnRH type-I and its receptor, were both upregulated. The expression levels of selected steroidogenic genes were also significantly altered. Moreover, a consistent enantioselective interference of hormone signaling was observed, and S-BF had greater effects than R-BF. Using molecular docking, the enantioselective endocrine disruption of BF was predicted to be partially due to enantiospecific ER binding affinity. Thus, BF could act through ER to enantioselectively disturb the hormonal network in trophoblast cells. These converging results suggest that the currently used chiral pesticides are of significant concern with respect to maternal-fetal health.

Stomatal behaviors reflect enantioselective phytotoxicity of chiral herbicide dichlorprop in Arabidopsis thaliana

“…As the different interactions with biological macromolecules like enzymes and nucleic acids, enantiomers of chiral herbicides may show opposite herbicidal activity though sharing the same physical and chemical properties (Diao et al, 2010;He et al, 2015;Liu et al, 2013;Liu et al, 2012;Wen et al, 2011;Zhao et al, 2014). In the present study, the DCPP enantiomers showed obvious enantioselective toxicity, which was consistent with previous studies (Wen et al, 2010;Wu et al, 2011).…”

Effects of metals on enantioselective toxicity and biotransformation of cis‐bifenthrin in zebrafish

“…Reverse transcription of 0.5 mg of total RNA was performed for the synthesis of the first-strand complementary DNA using the ReverTra Ace 1 qPCR RT kit (Toyobo) [39]. The relative levels of mRNA were normalized to the housekeeping gene b-actin and calculated using the 2 -DDCT method [42]. The oligonucleotide primers for each gene were designed using OMIGA Ver 2.0 software (Oxford Molecular) and are presented in the Supplemental Data, Table S1.…”

Alteration of the Enantioselective Toxicity of Diclofop Acid by Nonylphenol: Effect on Ascorbate‐Glutathione Cycle inMicrocystis Aeruginosa

“…Enantiomers of chiral compounds often exhibit different biological effects, i.e., enantioselective biochemical and toxicological effects . Such stereospecific biological effects have drawn much attention from researchers from the environmental field as well as people from the pharmaceutical and pesticide industries .…”

“…Enantiomers of chiral compounds often exhibit different biological effects, i.e., enantioselective biochemical and toxicological effects. [1][2][3][4][5][6][7] Such stereospecific biological effects have drawn much attention from researchers from the environmental field as well as people from the pharmaceutical and pesticide industries. 8,9 Therefore, many studies had investigated the effect of chiral compounds of environmental interest, not only on their ecological and health risk but also on their enantioselectivity including a wide range of persistent contaminants such as organochlorine pesticides (e.g., DDTs) and PCBs as well as emerging contaminants such as pharmaceuticals, phthalates, and particularly new pesticide substitutes.…”