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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BackgroundInfluential
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BackgroundInfluential
Co-exposure to Phytoestrogens and Bisphenol A mimic estrogenic effects in an additive manner
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“…(BPA), a well-described EDCs massively used by the plastic and resin industries, displays oestrogenic (Kuiper et al., 1998 ; Kitamura et al., 2005; Delfosse et al., 2012), anti-107 androgenic (Wang et al., 2017), and anti-thyroid hormone activities (Moriyama et al., 2002) which could alter the…”
Background
Influence of Exposure to Bisphenols on Cardiac Structure/Function
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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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