Cited by 410Effects and risks of endocrine disrupting chemicalsEstrogen and related hormone effectsComputational Drug Discovery Methods

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Structural and mechanistic insights into bisphenols action provide guidelines for risk assessment and discovery of bisphenol A substitutes

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Delfosse, Vanessa, Grimaldi, Marina, Pons, Jean-Luc, Boulahtouf, Abdelhay, le Maire, Albane, Cavailles, Vincent, Labesse, Gilles, Bourguet, William, Balaguer, Patrick·2012·Proceedings of the National Academy of Sciences

DOI 10.1073/pnas.1203574109PMC PMC3443136

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Abstract

Bisphenol A (BPA) is an industrial compound and a well known endocrine-disrupting chemical with estrogenic activity. The widespread exposure of individuals to BPA is suspected to affect a variety of physiological functions, including reproduction, development, and metabolism. Here we report that the mechanisms by which BPA and two congeners, bisphenol AF and bisphenol C (BPC), bind to and activate estrogen receptors (ER) α and β differ from that used by 17β-estradiol. We show that bisphenols act as partial agonists of ERs by activating the N-terminal activation function 1 regardless of their effect on the C-terminal activation function 2, which ranges from weak agonism (with BPA) to antagonism (with BPC). Crystallographic analysis of the interaction between bisphenols and ERs reveals two discrete binding modes, reflecting the different activities of compounds on ERs. BPA and 17β-estradiol bind to ERs in a similar fashion, whereas, with a phenol ring pointing toward the activation helix H12, the orientation of BPC accounts for the marked antagonist character of this compound. Based on structural data, we developed a protocol for in silico evaluation of the interaction between bisphenols and ERs or other members of the nuclear hormone receptor family, such as estrogen-related receptor γ and androgen receptor, which are two known main targets of bisphenols. Overall, this study provides a wealth of tools and information that could be used for the development of BPA substitutes devoid of nuclear hormone receptor-mediated activity and more generally for environmental risk assessment.

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BackgroundMethod
Molecular interactions of bisphenols and analogs with glucocorticoid biosynthetic pathway enzymes: an in silico approach
Verma, G., Khan, M. F., Akhtar, W., Alam, M. M., Akhter, M., & Shaquiquzzaman, M. (2017) · Toxicology Mechanisms and Methods · doi:10.1080/15376516.2017.1356415 · Cited by 18
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Background
Structural basis for molecular recognition of G protein-coupled estrogen receptor by selected bisphenols
Liu, X., Xue, Q., Zhang, H., Fu, J., & Zhang, A. (2021) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2021.148558 · Cited by 18
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“There is growing evidence of the propensity for adverse effects based on in vitro cellular studies evaluating the biological activity and toxic effects of BPs (Cao et al. 2017; Delfosse et al. 2012).”
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Background
Computational insights on agonist and antagonist mechanisms of estrogen receptor α induced by bisphenol A analogues
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“Moreover, the mechanism of interaction between these two molecules and ER-α has been described in detail previously, and the analysis of crystal structures demonstrated how BPA acts as a weak agonist, while BPC acts as an antagonist [29].”
Background
Environmental endocrine disruptors and pregnane X receptor action: A review
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Background
Induction of reproductive injury by bisphenol A and the protective effects of cyanidin-3-O-glucoside and protocatechuic acid in rats
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Non-targeted metabolomics revealing the effects of bisphenol analogues on human liver cancer cells
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Human Estrogen Receptor Alpha Antagonists, Part 3: 3-D Pharmacophore and 3-D QSAR Guided Brefeldin A Hit-to-Lead Optimization toward New Breast Cancer Suppressants
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“79 [75] 4MGC ( UT) PA H12: olecules 20 2, 27, x F R P ER RE IE 6 of 39”
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ERα-agonist and ERβ-antagonist bifunctional next-generation bisphenols with no halogens: BPAP, BPB, and BPZ
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Effects of high-dose bisphenol A on the mouse oral mucosa: A possible link with oral cancers
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Bisphenol A
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High Content Screening Using New U2OS Reporter Cell Models Identifies Harmol Hydrochloride as a Selective and Competitive Antagonist of the Androgen Receptor
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“HG5LN MR and HG5LN PXR luciferase reporter cell lines were obtained by stable expression of individual ligand binding domains fused to GAL4 DNA binding domain in HG5LN (HeLa GAL4REx5-luciferase) cells, as previously described [28,33,34].”
Method
Crystal structure of human ERRg LBD in complex with bisphenol-B
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Comparison of the cytotoxicity of bisphenol A and its analogs on human placental BeWo cells
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Chigira, T., Nagatoishi, S., & Tsumoto, K. (2015) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2015.06.002 · Cited by 13
Is BPA only the tip of the iceberg? Occurrence and risk assessment of 32 bisphenol analogues in landfill leachate
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“For estrogen receptors (PDB ID: 3UUD) containing hERa-LBD (Y537S) served as co-crystal structure was obtained from the Protein Databank (https://www.rcsb.org/structure/3UUD) (Delfosse et al. 2012).”
Method
Photoelectrochemical cell with Co3O4/BiVO4 photoanode and CoFe2O4 cathode: An efficient persulfate activation system for organic pollutants degradation
Geng, X., Zhang, R., Zhang, P., Yuan, X., Yang, C., Hou, Y., Zhang, J., & Huang, M. (2025) · Journal of environmental chemical engineering · doi:10.1016/j.jece.2025.116073 · Cited by 12
Tris(4-hydroxyphenyl)ethane (THPE), a trisphenol compound, is antiestrogenic and can retard uterine development in CD-1 mice
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Bisphenol A analogues induce a feed-forward estrogenic response in zebrafish
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A structural signature motif enlightens the origin and diversification of nuclear receptors
Beinsteiner, B., Markov, G. V., Erb, S., Chebaro, Y., McEwen, A. G., Cianférani, S., Laudet, V., Moras, D., & Billas, I. M. L. (2021) · PLoS Genetics · doi:10.1371/journal.pgen.1009492 · Cited by 14
“It is in particular the case for EcR (Billas et al., 2003), ER (Nettles et al., 2007), VDR (Belorusova and Rochel, 2016; Ciesielski et al., 2007), PXR (Delfosse et al., 2012), and many other NRs.”
Background
Endocrine disrupting chemicals (EDCs) and sex steroid receptors
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Peripubertal Bisphenol A Exposure Imparts Detrimental Age-Related Changes in Body Composition, Cognition, and Hydrogen Sulfide Production Capacities
Yang, J., Link, C., Henderson, Y. O., Bithi, N., & Hine, C. (2021) · Antioxidants and Redox Signaling · doi:10.1089/ars.2020.8226 · Cited by 12
“Maximal disruption of endocrine homeostasis by EDCs is believed to be during fetal and early postnatal life (45).”
BackgroundInfluential
Phytoecdysteroids and Anabolic Effect of Atriplex dimorphostegia: UPLC-PDA-MS/MS Profiling, In Silico and In Vivo Models
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Migration of Bisphenol A and Its Derivatives From Epoxy Coatings and Demand for BPA‐NI Products: Scientific Insights and Perspectives Leading to Regulation (EU) 2024/3190
Kajiyama, T., Kanazaki, K., Gopinath, V., Abdul‐Rahman, P. S., & Matsushima, A. (2025) · Chemistry - An Asian Journal · doi:10.1002/asia.202500340 · Cited by 11
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Mazzeo, D. E. C., Dombrowski, A., Oliveira, F. A., Levy, C. E., Oehlmann, J., & de Marchi, M. R. R. (2023) · Journal of Environmental Management · doi:10.1016/j.jenvman.2022.117207 · Cited by 11
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Bonaldo, B., Casile, A., Ostuni, M. T., Bettarelli, M., Nasini, S., Marraudino, M., Panzica, G., & Gotti, S. (2023) · Chemosphere · doi:10.1016/j.chemosphere.2023.140827 · Cited by 11
Interactions of bisphenol diglycidyl ethers with estrogen receptors α: Fluorescence polarization, reporter gene, and molecular modeling investigations
Zhang, J., Lv, C., Li, Z., Guan, T., Wang, Y., Li, T., & Zhang, T. (2020) · Toxicology Letters · doi:10.1016/j.toxlet.2020.06.023 · Cited by 11
A novel chemo-phenotypic method identifies mixtures of salpn, vitamin D3, and pesticides involved in the development of colorectal and pancreatic cancer
Issa, N. T., Wathieu, H., Glasgow, E. F., Peran, I., Parasido, E., Li, T., Simbulan-Rosenthal, C. M., Rosenthal, D. S., Medvedev, A. V., Makarov, S. S., et al. (2022) · Ecotoxicology and Environmental Safety · doi:10.1016/j.ecoenv.2022.113330 · Cited by 11
“CPTM predicted that these ECs bind to estrogen receptor alpha (ESR1), which is confirmed by an available crystal structure (Delfosse et al., 2012).”
Background
Bisphenol S induces Agrp expression through GPER1 activation and alters transcription factor expression in immortalized hypothalamic neurons: A mechanism distinct from BPA-induced upregulation
Xu, K. J., Loganathan, N., & Belsham, D. D. (2022) · Molecular and Cellular Endocrinology · doi:10.1016/j.mce.2022.111630 · Cited by 11
Species Differences in Response to Binding Interactions of Bisphenol A and its Analogs with the Modeled Estrogen Receptor 1 and In Vitro Reporter Gene Assay in Human and Zebrafish
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“Glu353 and His524 interactions have been commonly observed in previous studies (Cao et al., 2017; Cavaliere et al., 2020; Delfosse et al., 2012; Jeong et al., 2019; Li et al., 2015).”
Result
Expanding the structural footprint of xenoestrogens
Baker, M. E. (2014) · Endocrine Disruptors · doi:10.4161/23273739.2014.967138 · Cited by 11
NMR WaterLOGSY Reveals Weak Binding of Bisphenol A with Amyloid Fibers of a Conserved 11 Residue Peptide from Androgen Receptor
Asencio‐Hernández, J., Kieffer, B., & Delsuc, M. (2016) · PLoS ONE · doi:10.1371/journal.pone.0161948 · Cited by 11
“Direct evidence of BPA binding to the LBD of ER and AR has recently been provided [4, 5].”
Background
Induction of fibrosis following exposure to bisphenol A and its analogues in 3D human uterine leiomyoma cultures
Liu, J., Yu, L. C., Castro, L., Yan, Y., Bushel, P. R., Scappini, E., & Dixon, D. (2024) · Journal of Hazardous Materials · doi:10.1016/j.jhazmat.2024.134772 · Cited by 10
Bisphenols: Endocrine Disruptors and Their Impact on Fish: A Review
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Probing the toxic mechanism of bisphenol A with acid phosphatase at the molecular level
Xu, M., Zhang, R., Song, W., Zong, W., & Liu, R. (2018) · Environmental Science and Pollution Research · doi:10.1007/s11356-018-1378-7 · Cited by 10
Reprint of “In silico methods in the discovery of endocrine disrupting chemicals”
Vuorinen, A., Odermatt, A., & Schuster, D. (2015) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2015.08.015 · Cited by 10
Development of a molecular recognition based approach for multi-residue extraction of estrogenic endocrine disruptors from biological fluids coupled to liquid chromatography-tandem mass spectrometry measurement
Bousoumah, R., Antignac, J., Camel, V., Grimaldi, M., Balaguer, P., Courant, F., Bichon, E., Morvan, M., & Bizec, B. L. (2015) · Analytical and Bioanalytical Chemistry · doi:10.1007/s00216-015-9024-4 · Cited by 10
The SARS-CoV-2 spike protein binds and modulates estrogen receptorsPreprint
Solís, Ó., Beccari, A. R., Iaconis, D., Talarico, C., Ruiz-Bedoya, C. A., Nwachukwu, J. C., Cimini, A., Castelli, V., Bertini, R., Montopoli, M., et al. (2022) · bioRxiv (Cold Spring Harbor Laboratory) · doi:10.1101/2022.05.21.492920 · Cited by 10
A detailed theoretical exploration on the THR-β binding affinities and antioxidant activity of some halogenated bisphenols
Gheshlaghi, S. Z., Ebrahimi, A., & Faghih, Z. (2021) · Journal of Biomolecular Structure and Dynamics · doi:10.1080/07391102.2021.1950568 · Cited by 9
“Some halogenated phenolic compounds from algae such as halogenated bisphenols structurally resemble the thyroid hormones (Erin et al., 2018; Vanessa et al., 2012).”
Background
In Vivo and in Silico Assessments of Estrogenic Potencies of Bisphenol a and its Analogs in Zebrafish (Danio Rerio): Validity of in Silico Approaches to Predict in Vivo Effects
Kubota, A., Hirano, M., Yoshinouchi, Y., Chen, X., Nakamura, M., Wakayama, Y., Lee, J., Nakata, H., Iwata, H., & Kawai, Y. K. (2023) · Comparative Biochemistry and Physiology Part C Toxicology & Pharmacology · doi:10.1016/j.cbpc.2023.109619 · Cited by 9
Quantitation of Thyroid Hormone Binding to Anti-Thyroxine Antibody Fab Fragment by Native Mass Spectrometry
Thangaraj, S. K., Arola, H. O., Tullila, A., Nevanen, T. K., Rouvinen, J., & Jänis, J. (2019) · ACS Omega · doi:10.1021/acsomega.9b02659 · Cited by 9
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“Our previous study indicated that Glu356 plays important roles in the interactions of medaka ERα (unpublised data) and human ERα (Delfosse et al., 2012) with bisphenol analogs, including bisphenol A.”
Background
Human Estrogen Receptor α Antagonists. Part 1: 3-D QSAR-Driven Rational Design of Innovative Coumarin-Related Antiestrogens as Breast Cancer Suppressants through Structure-Based and Ligand-Based Studies
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“All these BPA substitutes have a common structure of two hydroxyphenyl functional groups and are collectively termed as bisphenol analogs (BPs) (Delfosse et al. 2012).”
Background
Vegetable oil-based hybrid microparticles as a green and biocompatible system for subcutaneous drug delivery
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“Additionally, more evidence suggests that ERs also exist in mollusks [23–27].”
Profile, Tissue Distribution, and Time Trend of Bisphenol Plastic Additives in Freshwater Wildlife of the Pearl River Ecosystem, China
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“been developed and used as substitutes in various plastic products, epoxy resins, papers, and other commercial and industrial products (Bjornsdotter et al., 2019; Chen et al., 2016; Delfosse et al., 2012; Qadeer et al., 2022; Usma & Ahmad, 2016).”
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“The crystal structure of the ER-LBD (PDB 3UUD) [38] was selected for virtual screening as it carries the Y537S mutation which stabilizes the active state of ER in the absence of ligands and confers resistance to tamoxifen [39].”
Influential
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Background
In vivo and in silico analyses of estrogenic potential of equine estrogens in medaka (Oryzias latipes)
Ishibashi, H., Uchida, M., Hirano, M., Hayashi, T., Yamamoto, R., Kubota, A., Ichikawa, N., Ishibashi, Y., Tominaga, N., & Arizono, K. (2020) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2020.144379 · Cited by 7
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Association between in vitro nuclear receptor-activating profiles of chemical compounds and their in vivo hepatotoxicity in rats
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“Bisphenol A and its analogs widely used as plasticizers, stabilizers and antioxidants for plastics are concerned about endocrine disrupting effects via activating estrogen receptor α/β (Delfosse et al., 2012).”
Understanding glycidylation reaction for the formation of pure mono, diglycidyl and dual monomers as glycidyl methacrylate of vanillyl alcohol
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“…step we detected the location for all cavities (where cavity or pocket is defined as the region of receptor to which a ligand may energetically be hosted) in the Estrogen Receptor alpha structure co-crystallized with either BPA (PDBcode: 3uu7) or with EST (PDBcode: 1a52) (Delfosse et al., 2012).”
Background
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ERα dimerization: a key factor for the weak estrogenic activity of an ERα modulator unable to compete with estradiol in binding assays
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“As described with bisphenol A (51,52), this suspected instability might be ascribed to a lack of key contacts between ESTZ and residues of this pocket (53).”
Background
BPA and risk assessment
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Bisphenol TMC exhibits greater estrogenic activity than Bisphenol A and three other structural analogues exemplified by higher estrogen receptor α-mediated gene expression and breast cancer cell proliferation
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Geffroy, F., Christophe, A., Piccini, B., Hinfray, N., Chadili, E., Maillot‐Maréchal, E., Cousin, X., Blanc, M., Charlier, T. D., Pandard, P., et al. (2026) · Environmental Science & Technology · doi:10.1021/acs.est.5c17875 · Cited by 4
Methylimidazolium ionic liquids - A new class of forever chemicals with endocrine disrupting potential
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Authors: Delfosse, V., Grimaldi, M., Pons, J.-L., Boulahtouf, A., le Maire, A., Cavailles, V., Labesse, G., Bourguet, W., & Balaguer, P.
Affiliations: Centre National de la Recherche Scientifique (FR)
Inserm (FR)
Centre de Biochimie Structurale, Institut National de la Santé et de la Recherche Médicale U1054, Centre National de la Recherche Scientifique, Unité Mixte de Recherche 5048, Universités Montpellier 1 and 2, 34090 Montpellier, France; and
Institut de Recherche en Cancérologie de Montpellier, Institut National de la Santé et de la Recherche Médicale U896, Centre Régional de Lutte contre le Cancer Val d’Aurelle Paul Lamarque, Université Montpellier 1, 34298 Montpellier, France
ORCID: Delfosse, Vanessa
Boulahtouf, Abdelhay
Labesse, Gilles
Bourguet, William
Balaguer, Patrick
Venue: Proceedings of the National Academy of Sciences
Publisher: National Academy of Sciences
Published: 2012-08-27
Volume: 109
Issue: 37
Pages: 14930-14935
ISSN: 0027-8424 (ISSN-L)
1091-6490
DOI: 10.1073/pnas.1203574109
PMC: PMC3443136
OpenAlex: W2140633565
Cited by: 405
References: 45
Citations by year: 2026: 28 · 2025: 33 · 2024: 26 · 2023: 33 · 2022: 34 · 2021: 40 · 2020: 38 · 2019: 35 · 2018: 25 · 2017: 26 · 2016: 19 · 2015: 25 · 2014: 23 · 2013: 20
FWCI: 15.31
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Locations: Proceedings of the National Academy of Sciences (publishedVersion)
Europe PMC (PubMed Central) (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
HAL (submittedVersion, other-oa)
Topics: Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Effects and risks of endocrine disrupting chemicals
Life Sciences › Biochemistry, Genetics and Molecular Biology › Endocrinology › Estrogen and related hormone effects
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Drug Discovery › Computational Drug Discovery Methods
Keywords: bisphenol A, bisphenol AF, bisphenol C, estrogen receptor alpha, estrogen receptor beta, endocrine disruptors, partial agonists, estrogen receptor antagonism, crystal structure, estrogen-related receptor gamma, androgen receptor, nuclear receptors, BPA substitutes, risk assessment, virtual screening
MeSH terms: Bisphenol A Compounds, Animals, Benzhydryl Compounds, Cell Line, Chromatography, Gel, Crystallography, Dose-Response Relationship, Drug, Estradiol, Fluorescence Polarization, Humans, Luciferases, Models, Molecular, Phenols, Oncorhynchus mykiss, Receptors, Cytoplasmic and Nuclear, Reverse Transcriptase Polymerase Chain Reaction, Estrogen Receptor alpha, Estrogen Receptor beta, Endocrine Disruptors

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Structural and mechanistic insights into bisphenols action provide guidelines for risk assessment and discovery of bisphenol A substitutes

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