Spectroscopic and molecular modeling approaches to investigate the interaction of bisphenol A, bisphenol F and their diglycidyl ethers with PPARα. (August 2017)

• Record Type: Journal Article
• Authors: Zhang, Jie; Zhang, Tiehua; Guan, Tianzhu; Ruan, Ping; Ren, Dayong; Dai, Weichang; Yu, Hansong; Li, Tiezhu
• Is Part Of: Chemosphere. Volume 180(2017)
• Page Start: 253
• Page End: 258
• Publication Date: 2017-08
• Subjects: Peroxisome proliferator-activated receptor -- Bisphenols -- Fluorescence polarization -- Molecular docking; Pollution -- Periodicals; Pollution -- Physiological effect -- Periodicals; Environmental sciences -- Periodicals; Atmospheric chemistry -- Periodicals; 551.511
• DOI: 10.1016/j.chemosphere.2017.04.034
• Languages: English
• ISSNs: 0045-6535

Abstract

Abstract: A fluorescence polarization (FP) assay for the simultaneous determination of bisphenol A (BPA), bisphenol F (BPF), bisphenol A diglycidyl ether (BADGE) and bisphenol F diglycidyl ether (BFDGE) was developed. The method was based on the competition between bisphenols (BPs) and fluorescein-labeled dexamethasone derivative (Dex-fl) for mouse peroxisome proliferator-activated receptor α ligand binding domain (mPPARα-LBD). A recombinant soluble protein derivative mPPARα-LBD* was prepared, then in vitro binding of 4 BPs to mPPARα-LBD* was investigated. Fluorescence polarization assay showed that these compounds exhibited different binding potencies with mPPARα-LBD*. Additionally, molecular dynamics simulations were performed to further understand the mechanism of BPs binding affinity for mPPARα-LBD*. Docking results elucidated that the driving forces for the binding of BPs to mPPARα-LBD* were predominantly dependent on hydrophobic and hydrogen-bonding interactions. Comparison of the calculated binding energies vs. experimental binding affinities yielded a good correlation (R 2 = 0.7258). The proposed method has potential for multi-residue detection of BPA, BPF, BADGE, and BFDGE. Graphical abstract: Highlights: Interaction of BPA, BPF, BADGE, and BFDGE with mPPARα-LBD* was investigated. The derivatives exhibited stronger binding potencies than their parent molecules. The mechanism of BPs-mPPARα-LBD* binding was illustrated by molecular docking. The proposed method can be used for preliminary screening of these compounds.