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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Background
Bisphenol S instead of bisphenol A: a story of reproductive disruption by regretable substitution - a review
Žalmanová, T., Hošková, K., Nevoral, J., Prokešová, Š., Zámostná, K., Kott, T., & Petr, J. (2016) · Czech Journal of Animal Science · doi:10.17221/81/2015-cjas · Cited by 74
Structural and functional evidences for the interactions between nuclear hormone receptors and endocrine disruptors at low doses
Balaguer, P., Delfosse, V., Grimaldi, M., & Bourguet, W. (2017) · Comptes Rendus Biologies · doi:10.1016/j.crvi.2017.08.002 · Cited by 82
Endocrine disruptors of sex hormone activities
Varticovski, L., Stavreva, D. A., McGowan, A., Raziuddin, R., & Hager, G. L. (2021) · Molecular and Cellular Endocrinology · doi:10.1016/j.mce.2021.111415 · Cited by 75
Developmental exposure to bisphenol A alters expression and DNA methylation of Fkbp5, an important regulator of the stress response
Kitraki, E., Nalvarte, I., Alavian‐Ghavanini, A., & Rüegg, J. (2015) · Molecular and Cellular Endocrinology · doi:10.1016/j.mce.2015.09.028 · Cited by 74
Endocrine Disrupting Chemicals, Hormone Receptors, and Acne Vulgaris: A Connecting Hypothesis
Rao, A., Douglas, S. C., & Hall, J. M. (2021) · Cells · doi:10.3390/cells10061439 · Cited by 74
“Evidence suggests that this is also true for EDCs, as EDCbound ERs were shown to associate with transcriptional coactivators in a manner that differed from estradiol or other ER ligands [59,60].”
Background
Androgen and Progesterone Receptors Are Targets for Bisphenol A (BPA), 4-Methyl-2,4-bis-(P-Hydroxyphenyl)Pent-1-Ene—A Potent Metabolite of BPA, and 4-Tert-Octylphenol: A Computational Insight
Rehan, M., Ahmad, E., SHEIKH, I. A., Abuzenadah, A. M., Damanhouri, G. A., Bajouh, O. S., AlBasri, S. F., Assiri, M. M., & Beg, M. A. (2015) · PLoS ONE · doi:10.1371/journal.pone.0138438 · Cited by 74
Understanding the Molecular Basis for Differences in Responses of Fish Estrogen Receptor Subtypes to Environmental Estrogens
Tohyama, S., Miyagawa, S., Lange, A., Ogino, Y., Mizutani, T., Tatarazako, N., Katsu, Y., Ihara, M., Tanaka, H., Ishibashi, H., et al. (2015) · Environmental Science & Technology · doi:10.1021/acs.est.5b00704 · Cited by 72
Versatility or Promiscuity: The Estrogen Receptors, Control of Ligand Selectivity and an Update on Subtype Selective Ligands
Ng, H. W., Perkins, R., Tong, W., & Hong, H. (2014) · International Journal of Environmental Research and Public Health · doi:10.3390/ijerph110908709 · Cited by 71
“6 [64] 4DMA Dimer 2’-Bromo-6’-(furan-3-yl)-4’-(hydroxymethyl)biphenyl-4-ol 2.”
BackgroundInfluential
Bisphenols emerging in Norwegian and Czech aquatic environments show transthyretin binding potency and other less-studied endocrine-disrupting activities
Šauer, P., Švecová, H., Grabicová, K., Aydın, F. G., Mackuľak, T., Kodeš, V., Blytt, L. D., Henninge, L. B., Grabic, R., & Kroupová, H. K. (2020) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2020.141801 · Cited by 69
The promiscuous estrogen receptor: Evolution of physiological estrogens and response to phytochemicals and endocrine disruptors
Baker, M. E., & Lathe, R. (2018) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2018.07.001 · Cited by 70
Allosteric Controls of Nuclear Receptor Function in the Regulation of Transcription
Billas, I. M. L., & Moras, D. (2013) · Journal of Molecular Biology · doi:10.1016/j.jmb.2013.03.017 · Cited by 71
“As an illustration, we mention here the recent crystallographic analysis of the interaction between the estrogen receptors and bisphenols, which are well-documented endocrine disruptors with estrogenic activity.(46) The crystal structures of ERs in complex with BPA (bisphenol A) and its chemical derivatives reveal two…”
Background
Full antagonism of the estrogen receptor without a prototypical ligand side chain
Srinivasan, S., Nwachukwu, J. C., Bruno, N. E., Dharmarajan, V., Goswami, D., Kastrati, I., Novick, S. J., Nowak, J., Cavett, V. J., Zhou, H., et al. (2016) · Nature Chemical Biology · doi:10.1038/nchembio.2236 · Cited by 66
A Computational Assay of Estrogen Receptor α Antagonists Reveals the Key Common Structural Traits of Drugs Effectively Fighting Refractory Breast Cancers
Pavlin, M., Spinello, A., Pennati, M., Zaffaroni, N., Gobbi, S., Bisi, A., Colombo, G., & Magistrato, A. (2018) · Scientific Reports · doi:10.1038/s41598-017-17364-4 · Cited by 69
Perturbation of Nuclear Hormone Receptors by Endocrine Disrupting Chemicals: Mechanisms and Pathological Consequences of Exposure
Hall, J. M., & Greco, C. W. (2019) · Cells · doi:10.3390/cells9010013 · Cited by 66
“EDCs are known to differentially associate with transcriptional coactivators compared with estradiol or other ER-alpha and ER-beta ligands [34,35], and thus, the degree of agonist/antagonist activity of specific EDCs on a particular receptor may in part reflect the degree of cofactor association.”
Background
Occurrence, spatial distribution, and main source identification of ten bisphenol analogues in the dry season of the Pearl River, South China
Wang, H., Tang, Z., Liu, Z., Zeng, F., Zhang, J., & Dang, Z. (2022) · Environmental Science and Pollution Research · doi:10.1007/s11356-021-17647-4 · Cited by 66
“To fulfill the market demand, bisphenol analogues with chemical structures similar to BPA have been widely used, and some of them are gradually being used as substitutes for BPA (Chen et al. 2016; Delfosse et al. 2012; Liao et al. 2012; Xue et al. 2015; Banderakhshan et al. 2022).”
Background
In Silico Predictions of Endocrine Disruptors Properties
Schneider, M., Pons, J.-L., Labesse, G., & Bourguet, W. (2019) · Endocrinology · doi:10.1210/en.2019-00382 · Cited by 69
Emerging concepts and opportunities for endocrine disruptor screening of the non-EATS modalities
Martyniuk, C. J., Martínez, R., Navarro‐Martín, L., Kamstra, J. H., Schwendt, A., Reynaud, S., & Chalifour, L. E. (2021) · Environmental Research · doi:10.1016/j.envres.2021.111904 · Cited by 65
Selective Human Estrogen Receptor Partial Agonists (ShERPAs) for Tamoxifen-Resistant Breast Cancer
Xiong, R., Patel, H., Gutgesell, L. M., Zhao, J., Delgado-Rivera, L., Pham, T. D., Zhao, H., Carlson, K. E., Martin, T. A., Katzenellenbogen, J. A., et al. (2015) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.5b01276 · Cited by 63
Structures of Endocrine-Disrupting Chemicals Correlate with the Activation of 12 Classic Nuclear Receptors
Tan, H., Chen, Q., Hong, H., Benfenati, E., Gini, G. C., Zhang, X., Yu, H., & Shi, W. F. (2021) · Environmental Science & Technology · doi:10.1021/acs.est.1c04997 · Cited by 59
Experimental and computational insights on the recognition mechanism between the estrogen receptor α with bisphenol compounds
Cao, H., Wang, F., Liang, Y., Wang, H., Zhang, A., & Song, M. (2017) · Archives of Toxicology · doi:10.1007/s00204-017-2011-0 · Cited by 63
“According to the above docking results for the ligand-ERα complex, the NR box2 peptide (KILHRLLQE) coordinates (the chain C of 3UUD) were introduced manually into shallow activation function 2 (AF2) surfaces of ERα, which is representative of short LxxLL motifs of SRC-1 co-activators in breast cancer cells (Delfosse e…”
BackgroundMethodResultInfluential
Bisphenol-A disturbs hormonal levels and testis mitochondrial activity, reducing male fertility
Ryu, D., Pang, W., Adegoke, E. O., Rahman, M. S., Park, Y.-J., & Pang, M. (2023) · Human Reproduction Open · doi:10.1093/hropen/hoad044 · Cited by 60
“It has been well-established that BPA binds with ER a and ER b (Delfosse et al. , 2012; Kuiper et al. , 1998).”
Background
Bisphenol a regulates the estrogen receptor alpha signaling in developing hippocampus of male rats through estrogen receptor
Xu, X., He, Y., Song, C., Ke, X.-F., Fan, S.-J., Peng, W., Tan, R., Kawata, M., Matsuda, K., Pan, B.-X., et al. (2014) · Hippocampus · doi:10.1002/hipo.22336 · Cited by 59
“Mechanisms of how BPA exerts these actions are not well understood but may involve its estrogen-like ability to bind estrogen receptor (ER; Papaconstantinou et al., 2000, 2001; Delfosse et al., 2012), which is postulated to disrupt the normal ER signaling in the target neurons.”
BackgroundInfluential
In silico methods in the discovery of endocrine disrupting chemicals
Vuorinen, A., Odermatt, A., & Schuster, D. (2013) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2013.04.009 · Cited by 58
Neuroendocrine and behavioral effects of maternal exposure to oral bisphenol A in female mice
Naulé, L., Picot, M., Martini, M., Parmentier, C., Hardin‐Pouzet, H., Keller, M., Franceschini, I., & Mhaouty‐Kodja, S. (2014) · Journal of Endocrinology · doi:10.1530/joe-13-0607 · Cited by 63
“Known for its estrogenic activity, BPA binds to estrogen receptors (ERs) with a lower afﬁnity than that of estradiol (E 2 ) (Dodds & Lawson 1936) and acts as a partial agonist (Delfosse et al .”
Background
Occurrence and fate of bisphenol A transformation products, bisphenol A monomethyl ether and bisphenol A dimethyl ether, in wastewater treatment plants and surface water
Ashfaq, M. A., Sun, Q., Zhang, H., Li, Y., Wang, Y., Li, M., Lv, M., Liao, X., & Yu, C. (2018) · Journal of Hazardous Materials · doi:10.1016/j.jhazmat.2018.06.022 · Cited by 58
Bisphenol AP is anti-estrogenic and may cause adverse effects at low doses relevant to human exposure
Xiao, X., Li, J., Yu, T., Zhou, L., Fan, X., Xiao, H., Wang, Y., Yang, L., Lv, J., Jia, X., et al. (2018) · Environmental Pollution · doi:10.1016/j.envpol.2018.07.115 · Cited by 58
Profile and removal of bisphenol analogues in hospital wastewater, landfill leachate, and municipal wastewater in South China
Huang, Z. W., Zhao, J., Zhang, C., Rao, W.-L., Liang, G., Zhang, H., Liu, Y.-H., Guan, Y., Zhang, H., & Ying, G. (2021) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2021.148269 · Cited by 59
Typical organic pollutant-protein interactions studies through spectroscopy, molecular docking and crystallography: A review
Tu, M., Zheng, X., Liu, P., Wang, S., Yan, Z., Sun, Q., & Liu, X. (2020) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2020.142959 · Cited by 57
Structure–activity relationships of bisphenol A analogs at estrogen receptors (ERs): Discovery of an ERα-selective antagonist
Maruyama, K., Nakamura, M., Tomoshige, S., Sugita, K., Makishima, M., Hashimoto, Y., & Ishikawa, M. (2013) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2013.05.067 · Cited by 57
Atomic Insights into Distinct Hormonal Activities of Bisphenol A Analogues toward PPARγ and ERα Receptors
Zhuang, S., Zhang, C., & Liu, W. (2014) · Chemical Research in Toxicology · doi:10.1021/tx500232b · Cited by 55
A Demonstration of the Uncertainty in Predicting the Estrogenic Activity of Individual Chemicals and Mixtures From anIn VitroEstrogen Receptor Transcriptional Activation Assay (T47D-KBluc) to theIn VivoUterotrophic Assay Using Oral Exposure
Conley, J. M., Hannas, B. R., Furr, J., Wilson, V. S., & Gray, L. E. (2016) · Toxicological Sciences · doi:10.1093/toxsci/kfw134 · Cited by 55
“…our current observations, in vitro studies on the ER binding affinity (Blair et al., 2000) and ER transcriptional activation and cell proliferation (Delfosse et al., 2012) activities of BPC have reported this compound to be more potent than other BPA analogues, as well as most other environmental…”
Background
BPA and its analogues (BPS and BPF) modify the expression of genes involved in the endocrine pathway and apoptosis and a multi drug resistance gene of the aquatic midge Chironomus riparius (Diptera)
Morales, M., de la Fuente, M., & Martín-Folgar, R. (2020) · Environmental Pollution · doi:10.1016/j.envpol.2020.114806 · Cited by 54
Combining `dry' co-crystallization andin situdiffraction to facilitate ligand screening by X-ray crystallography
Gelin, M., Delfosse, V., Allemand, F., Hoh, F., Sallaz-Damaz, Y., Pirocchi, M., Bourguet, W., Ferrer, J.-L., Labesse, G., & Guichou, J. (2015) · Acta Crystallographica Section D Biological Crystallography · doi:10.1107/s1399004715010342 · Cited by 54
“This result is of importance as nuclear receptors are the targets of about 20% of currently used drugs and of numerous environmental pollutants (Delfosse et al., 2012), the mode of binding of which still has to be deciphered for the vast majority.”
Background
Dual-iodine-doped BiOIO3: Bulk and surface co–modification for enhanced visible-light photocatalytic removal of bisphenol AF
Zhu, Z., Zhang, Q., Xiao, X., Sun, F., Zuo, X., & Nan, J. (2020) · Chemical Engineering Journal · doi:10.1016/j.cej.2020.126543 · Cited by 54
Role of Bottle Feeding in the Etiology of Hypertrophic Pyloric Stenosis
McAteer, J. P., Ledbetter, D. J., & Goldin, A. B. (2013) · Archives of Pediatrics and Adolescent Medicine · doi:10.1001/jamapediatrics.2013.2857 · Cited by 53
Predictive features of ligand‐specific signaling through the estrogen receptor
Nwachukwu, J. C., Srinivasan, S., Zheng, Y., Wang, S., Min, J., Dong, C., Liao, Z., Nowak, J., Wright, N. A., Houtman, R., et al. (2016) · Molecular Systems Biology · doi:10.15252/msb.20156701 · Cited by 53
“…2016 The Authors Molecular Systems Biology 12: 864 | 2016 ERa-Y537S LBDs, demonstrating again that this surface mutation stabilizes h12 dynamics to facilitate crystallization without changing ligand binding (Appendix Fig S1A and B) (Nettles et al, 2008; Bruning et al, 2010; Delfosse et al, 2012).”
Background
Structure-Based Understanding of Binding Affinity and Mode of Estrogen Receptor α Agonists and Antagonists
Lee, S., & Barron, M. G. (2017) · PLoS ONE · doi:10.1371/journal.pone.0169607 · Cited by 53
Bisphenols and Risk of Breast Cancer: A Narrative Review of the Impact of Diet and Bioactive Food Components
Stillwater, B. J., Bull, A., Romagnolo, D. F., Neumayer, L. A., Donovan, M. G., & Selmin, O. I. (2020) · Frontiers in Nutrition · doi:10.3389/fnut.2020.581388 · Cited by 52
“Excellent reviews of biochemical mechanisms of actions of BPA are available elsewhere (22).”
Background
Coexposure to Phytoestrogens and Bisphenol A Mimics Estrogenic Effects in an Additive Manner
Katchy, A., Pinto, C. L., Jonsson, P., Nguyen-Vu, T., Pandelova, M. E., Riu, A., Schramm, K., Samarov, D. V., Gustafsson, J.-Α., Bondesson, M., et al. (2013) · Toxicological Sciences · doi:10.1093/toxsci/kft271 · Cited by 55
“(Delfosse et al., 2012), reaching a maximal activation of only 70-80% relative to E2 (Figure 1A”
Background
Cyclodextrin self-assembled graphene oxide aerogel microspheres as broad-spectrum adsorbent for removing dyes and organic micropollutants from water
Nie, Z.-J., Guo, Q., Xia, H., Song, M.-M., Qiu, Z., Fan, S.-T., Chen, Z., Zhang, S., Zhang, S., & Li, B. (2020) · Journal of environmental chemical engineering · doi:10.1016/j.jece.2020.104749 · Cited by 52
Selectivity of natural, synthetic and environmental estrogens for zebrafish estrogen receptors
Pinto, C. L., Grimaldi, M., Boulahtouf, A., Pakdel, F., Brion, F., Aı̈t-Aı̈ssa, S., Cavaillès, V., Bourguet, W., Gustafsson, J.-Α., Bondesson, M., et al. (2014) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2014.07.020 · Cited by 51
“Similarly to human ERs (Delfosse et al., 2012), bisphenol A (BPA) acted as a partial agonist towards the 3 zfERs (Fig.”
BackgroundMethodInfluential
Estrogen and Bisphenol A Affect Male Rat Enamel Formation and Promote Ameloblast Proliferation
Jedeon, K., Loiodice, S., Marciano, C., Vinel, A., Lavier, M.-C. C., Berdal, A., & Babajko, S. (2014) · Endocrinology · doi:10.1210/en.2013-2161 · Cited by 51
“and ER with an equilibrium dissociation constant (Kd) of about 100 nM (17, 18, 19).”
Background
Predicting anti-androgenic activity of bisphenols using molecular docking and quantitative structure-activity relationships
Yang, X., Liu, H., Yang, Q., Liu, J., Chen, J., & Shi, L. (2016) · Chemosphere · doi:10.1016/j.chemosphere.2016.08.062 · Cited by 54
Binding of Androgen- and Estrogen-Like Flavonoids to Their Cognate (Non)Nuclear Receptors: A Comparison by Computational Prediction
D’Arrigo, G., Gianquinto, E., Rossetti, G., Cruciani, G., Lorenzetti, S., & Spyrakis, F. (2021) · Molecules · doi:10.3390/molecules26061613 · Cited by 58
“Crystallographic pose of E2 (a), and docking poses of NRG (b) and RESV (c) in ERα (PDB ID 3uud [72]).”
Influential
The Asymmetric Binding of PGC-1α to the ERRα and ERRγ Nuclear Receptor Homodimers Involves a Similar Recognition Mechanism
Takács, M., Petoukhov, M. V., Atkinson, R. A., Roblin, P., Ogi, F.-X., Demeler, B., Potier, N., Chebaro, Y., Dejaegere, A. P., Svergun, D. I., et al. (2013) · PLoS ONE · doi:10.1371/journal.pone.0067810 · Cited by 49
“The existence of allosteric control in the binding of ligands and/or coregulators to homodimeric receptors is much more intriguing, and has already been suggested for homodimeric RAR and ER [37,39], whereby the binding of a ligand and/or a coregulator to one of the receptor subunit can impact on the binding of the lig…”
Background
Allosteric small molecule modulators of nuclear receptors
Meijer, F. A., de Gevel, I. A. L.-V., de Vries, R. M. J. M., & Brunsveld, L. (2019) · Molecular and Cellular Endocrinology · doi:10.1016/j.mce.2019.01.022 · Cited by 50
“For both RARβ and the estrogen receptor α (ERα) it was observed that in the homodimer complex, this asymmetry was altering the binding mode of the ligand, as revealed for example via two different poses of the same ligand in each the two monomers.(33,34) Furthermore, it has been reported that also in the absence of a…”

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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