title: Molecular Dynamics Simulations of the Permeation of Bisphenol A and Pore Formation in a Lipid Membrane.
abstract: 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.
authors.affiliation: School of Sciences, Zhejiang A &F University, Lin'an 311300, China.|School of Environmental and Chemical Engineering, Shanghai University, 99 Shangda Road, Shanghai 200444, China.
authors.forename: Liang
authors.initials: L
authors.lastname: Chen
authors.affiliation: School of Sciences, Zhejiang A &F University, Lin'an 311300, China.
authors.forename: Junlang
authors.initials: J
authors.lastname: Chen
authors.affiliation: School of Sciences, Zhejiang A &F University, Lin'an 311300, China.
authors.forename: Guoquan
authors.initials: G
authors.lastname: Zhou
authors.affiliation: School of Sciences, Zhejiang A &F University, Lin'an 311300, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Key Lab for Magnetism and Magnetic Materials of MOE, Lanzhou University, Lanzhou 73000, China.
authors.forename: Can
authors.initials: C
authors.lastname: Xu
authors.affiliation: School of Sciences, Zhejiang A &F University, Lin'an 311300, China.
authors.forename: Xiaogang
authors.initials: X
authors.lastname: Wang
mesh_terms: D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry; D001559:Benzhydryl Compounds / Q000378:metabolism*; D002463:Cell Membrane Permeability; D008051:Lipid Bilayers / Q000378:metabolism*; D056004:Molecular Dynamics Simulation; D010636:Phenols / Q000378:metabolism*; D016062:Porosity; D012995:Solubility; D014867:Water / Q000737:chemistry; D000098826:Bisphenol A Compounds
chemical_list: D015060:1,2-Dipalmitoylphosphatidylcholine; D001559:Benzhydryl Compounds; D008051:Lipid Bilayers; D010636:Phenols; D014867:Water; C006780:bisphenol A; D000098826:Bisphenol A Compounds