ArticlePloS one2012
3D models of MBP, a biologically active metabolite of bisphenol A, in human estrogen receptor α and estrogen receptor β.
Article in PloS one, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
15 citing papers in PubMed, 55 citations in OpenAlex.
- Review
- 4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (MBP) exposure induces hepatotoxicity and nephrotoxicity - role of oxidative stress, mitochondrial dysfunction and pathways of cytotoxicity.Toxicology research · 2024Article
- The Conflict between Regulatory Agencies over the 20,000-Fold Lowering of the Tolerable Daily Intake (TDI) for Bisphenol A (BPA) by the European Food Safety Authority (EFSA).Environmental health perspectives · 2024Article
- Endocrine-Disrupting Chemicals and Their Adverse Effects on the Endoplasmic Reticulum.International journal of molecular sciences · 2022Review
- Update on the Health Effects of Bisphenol A: Overwhelming Evidence of Harm.Endocrinology · 2021Review
- Complete Genome Sequence of Bisphenol A-Degrading BacteriumMicrobiology resource announcements · 2021Article
- Genome-Wide Analysis of Low Dose Bisphenol-A (BPA) Exposure in Human Prostate Cells.Current genomics · 2019Article
- hCG and Its Disruption by Environmental Contaminants during Human Pregnancy.International journal of molecular sciences · 2018Review
- Oxyresveratrol Is a Phytoestrogen Exerting Anti-inflammatory Effects Through NF-κB and Estrogen Receptor Signaling.Inflammation · 2017Article
- Effects of Bisphenol A Metabolite 4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene on Lung Function and Type 2 Pulmonary Alveolar Epithelial Cell Growth.Scientific reports · 2016Article
- Article
- Transcriptional analysis of endocrine disruption using zebrafish and massively parallel sequencing.Journal of molecular endocrinology · 2014Review
- Bisphenol A alters β-hCG and MIF release by human placenta: an in vitro study to understand the role of endometrial cells.Mediators of inflammation · 2014Article
- Article
- Biological Tools to Study the Effects of Environmental Contaminants at the Feto-Maternal Interface.Dose-response : a publication of International Hormesis SocietyReview
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Bisphenol A [BPA] is a widely dispersed environmental chemical that is of much concern because the BPA monomer is a weak transcriptional activator of human estrogen receptor α [ERα] and ERβ in cell culture. A BPA metabolite, 4-methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene [MBP], has transcriptional activity at nM concentrations, which is 1000-fold lower than the concentration for estrogenic activity of BPA, suggesting that MBP may be an environmental estrogen. To investigate the structural basis for the activity of MBP at nM concentrations and the lower activity of BPA for human ERα and ERβ, we constructed 3D models of human ERα and ERβ with MBP and BPA for comparison with estradiol in these ERs. These 3D models suggest that MBP, but not BPA, has key contacts with amino acids in human ERα and ERβ that are important in binding of estradiol by these receptors. Metabolism of BPA to MBP increases the spacing between two phenolic rings, resulting in contacts between MBP and ERα and ERβ that mimic those of estradiol with these ERs. Mutagenesis of residues on these ERs that contact the phenolic hydroxyls will provide a test for our 3D models. Other environmental chemicals containing two appropriately spaced phenolic rings and an aliphatic spacer instead of an estrogenic B and C ring also may bind to ERα or ERβ and interfere with normal estrogen physiology. This analysis also may be useful in designing novel chemicals for regulating the actions of human ERα and ERβ.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.