Estrogen receptor-based fluorescence polarization assay for bisphenol analogues and molecular modeling study of their complexation mechanism

Zhang, Jie; Wu, Wenfu; Wang, Yongjun; Xing, XiaoJia; Zhong, Shuning; Guan, Tianzhu; Zhang, Tiehua; Hou, Ligang; Li, Tiezhu

doi:10.1016/j.aca.2018.05.034

Cited by 15 publications

(8 citation statements)

References 44 publications

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“…Among them, the phenolic hydroxyl group of coumestrol forms hydrogen bonds with the residues at the two ends of the binding cavity, and the hydrogen bond interactions are greater than other ligands, which helps to improve the binding stability of coumestrol to ER. According to the references [27][28][29][30] and the comparison of the docking results, it can be seen that the hydrogen bond interactions play an important stabilizing role in the ligand-receptor binding process. hydroxyl group of coumestrol forms hydrogen bonds with the residues at the two ends of the binding cavity, and the hydrogen bond interactions are greater than other ligands, which helps to improve the binding stability of coumestrol to ER.…”

Section: Molecular Dynamics Simulation Analysismentioning

confidence: 99%

Interaction of Coumarin Phytoestrogens with ERα and ERβ: A Molecular Dynamics Simulation Study

Wang

Zhuang

et al. 2020

Molecules

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Coumarin phytoestrogens, as one of the important classes of phytoestrogens, have been proved to play an important role in various fields of human life. In this study, molecular simulation method including molecular docking and molecular dynamics methods were performed to explore the various effects between four classical coumarin phytoestrogens (coumestrol, 4-methoxycoumestrol, psoralen and isopsoralen), and estrogen receptors (ERα, ERβ), respectively. The calculated results not only proved that the four coumarin phytoestrogens have weaker affinity than 17β-estradiol to both ERα, and ERβ, but also pointed out that the selective affinity for ERβ is greater than ERα. In addition, the binding mode indicated that the formation of hydrogen bond and hydrophobic interaction have an important effect on the stability of the complexes. Further, the calculation and decomposition of binding free energy explored the main contribution interactions to the total free energy.

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Section: Molecular Dynamics Simulation Analysismentioning

confidence: 99%

Interaction of Coumarin Phytoestrogens with ERα and ERβ: A Molecular Dynamics Simulation Study

Wang

Zhuang

et al. 2020

Molecules

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“…MD not only helps to elucidate bound conformations and binding energies between LBD and BPA in the ER [ 191 ], but it also gives insight into the influence of that binding on the whole protein, including the DBD. One of the studies [ 185 ] showed that the allosteric effects in the LBD due to BPA binding could cause relaxation of the DBD and, therefore, alter ER’s function. Other researchers reported the influence of bisphenol compounds on the protein’s allosteric modulation, altering the Helix12 stability and reducing the recruitment potency of co-activators [ 187 ].…”

Section: Application Of Molecular Modelling Methods In the Study Omentioning

confidence: 99%

Application of Various Molecular Modelling Methods in the Study of Estrogens and Xenoestrogens

Mazurek

Szeleszczuk

Simonson

et al. 2020

IJMS

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In this review, applications of various molecular modelling methods in the study of estrogens and xenoestrogens are summarized. Selected biomolecules that are the most commonly chosen as molecular modelling objects in this field are presented. In most of the reviewed works, ligand docking using solely force field methods was performed, employing various molecular targets involved in metabolism and action of estrogens. Other molecular modelling methods such as molecular dynamics and combined quantum mechanics with molecular mechanics have also been successfully used to predict the properties of estrogens and xenoestrogens. Among published works, a great number also focused on the application of different types of quantitative structure–activity relationship (QSAR) analyses to examine estrogen’s structures and activities. Although the interactions between estrogens and xenoestrogens with various proteins are the most commonly studied, other aspects such as penetration of estrogens through lipid bilayers or their ability to adsorb on different materials are also explored using theoretical calculations. Apart from molecular mechanics and statistical methods, quantum mechanics calculations are also employed in the studies of estrogens and xenoestrogens. Their applications include computation of spectroscopic properties, both vibrational and Nuclear Magnetic Resonance (NMR), and also in quantum molecular dynamics simulations and crystal structure prediction. The main aim of this review is to present the great potential and versatility of various molecular modelling methods in the studies on estrogens and xenoestrogens.

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“…Therefore, we need to explore a stabilized preparation method of the broad-spectrum receptor, to competitively bind with the tested molecules. To obtain the ER-LBD, the expression of the protein of interest fused with glutathione S-transferase (GST) was produced as already described by [28], and purification of the product by glutathione sepharose (GST) column.…”

Section: Methodsmentioning

confidence: 99%

Multi-Residue Method for the Analysis of Stilbene Estrogens in Milk

Guan

Sun

Wang

et al. 2019

IJMS

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The rapid analysis of stilbene estrogens is crucially important in the environment, food and health sectors, but quantitation of lower detection limit for stilbene estrogens persists as a severe challenge. We herein described a homologous and sensitive fluorescence polarization (FP) assay based on estrogen receptor α ligand binding domain (ER-LBD) to monitor stilbene estrogens in milk. Under optimal conditions, the half maximal inhibitory concentrations (IC50) of the FP assay were 9.27 nM, 12.94 nM, and 22.38 nM for hexestrol, dienestrol and diethylstilbestrol, respectively. And the corresponding limits of detection (LOD) values were 2.94 nM, 2.89 nM, and 3.12 nM. Finally, the assay was applied to determine the stilbenes in milk samples where the mean recoveries ranged from 95.76% to 112.78% and the coefficients of variation (CV) below 12.00%. Furtherly, we have focused our study on high cross-reactivity phenomena by using two in silico approaches, including molecular docking analysis and topology analysis. Overall, docking results show that several residues in the hydrophobic pocket produce hydrophobic interactions with the tested drug molecules, which contribute to the stability of their binding. In this paper, we conclude that the FP method is suitable for the rapid detection of stilbenes in milk samples, requiring no expensive analytical equipment or time-consuming sample preparation. This work offers a practical approach that applies bioscience technology in food safety testing and improves analytical speed and laboratory efficiency.

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Estrogen receptor-based fluorescence polarization assay for bisphenol analogues and molecular modeling study of their complexation mechanism

Cited by 15 publications

References 44 publications

Interaction of Coumarin Phytoestrogens with ERα and ERβ: A Molecular Dynamics Simulation Study

Interaction of Coumarin Phytoestrogens with ERα and ERβ: A Molecular Dynamics Simulation Study

Application of Various Molecular Modelling Methods in the Study of Estrogens and Xenoestrogens

Multi-Residue Method for the Analysis of Stilbene Estrogens in Milk

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