Molecular Dynamics Simulations of the Permeation of Bisphenol A and Pore Formation in a Lipid Membrane.

Liang Chen,Can Xu,Junlang Chen,Guoquan Zhou,Yu Wang,Xiaogang Wang

doi:10.1038/srep33399

Liang Chen, Can Xu + Show 4 more

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https://doi.org/10.1038/srep33399

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Bisphenol A (BPA) is particularly considered as one of the most suspicious endocrine disruptors. Exposure to BPA may bring about possible human toxicities, such as cancerous tumors, birth defects and neoteny. One of the key issues to understand its toxicities is how BPA enters cells. In this paper, we perform molecular dynamics simulations to explore the interactions between BPA and a phospholipid membrane (dipalmitoylphosphatidylcholine, DPPC bilayer). The simulation results show that BPA can easily enter the membrane from the aqueous phase. With the increasing concentrations of BPA in the membrane, BPA tends to aggregate and form into cluster. Meanwhile, several DPPC lipids are pulled out from each leaflet and adsorbed on the cluster surface, leading to pore formation. Detailed observations indicate that the lipid extraction results mainly from the dispersion interactions between BPA cluster and lipid tails, as well as weak electrostatic attractions between lipid headgroups and the two hydroxyl groups on BPA. The lipid extraction and pore formation may cause cell membrane damage and are of great importance to uncover BPA’s cytotoxicity.

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Bisphenol A (BPA), 2, 2-bis (4-hydroxyphenyl) propane, an important chemical material, is widely used to produce epoxy resins and polycarbonates[1,2]
BPA was adsorbed on the surface of bilayer because of the electrostatic interactions between the two hydroxyl groups of BPA and the lipid headgroups
The translocation and aggregation of BPA in a DPPC bilayer have been investigated by molecular dynamics simulations

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Introduction

Bisphenol A (BPA), 2, 2-bis (4-hydroxyphenyl) propane, an important chemical material, is widely used to produce epoxy resins and polycarbonates[1,2]. It is highlighted as one endocrine disrupting chemical[3,4,5], which may cause the function abnormalities of human endocrine system[6,7,8], including mimicking estrogen[9,10], occupying the hormone receptors, and disrupting hormone synthesis, secretion[11]. When aggregated in the membrane, BPA cluster can extract lipids and adsorb them on its surface, resulting in pore formation. Such effect has not been reported previously, and it may offer new insights for the toxicities of BPA

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