The DOI matches its Crossref record; 22 of the 22 references it cites were found in a registry or an index.
The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups.
Open accessAbstract
The chemical structure of hydroxylated diphenylalkanes or bisphenols consists of two phenolic rings joined together through a bridging carbon. This class of endocrine disruptors that mimic estrogens is widely used in industry, particularly in plastics. Bisphenol F, bisphenol A, fluorine-containing bisphenol A (bisphenol AF), and other diphenylalkanes were found to be estrogenic in a bioassay with MCF7 human breast cancer cells in culture (E-SCREEN assay). Bisphenols promoted cell proliferation and increased the synthesis and secretion of cell type-specific proteins. When ranked by proliferative potency, the longer the alkyl substituent at the bridging carbon, the lower the concentration needed for maximal cell yield; the most active compound contained two propyl chains at the bridging carbon. Bisphenols with two hydroxyl groups in the para position and an angular configuration are suitable for appropriate hydrogen bonding to the acceptor site of the estrogen receptor. Our data suggest that estrogenicity is influenced not only by the length of the substituents at the bridging carbon but also by their nature. Because diphenylalkane derivatives are widespread and their production and use are increasing, potential exposure of humans to estrogenic bisphenols is becoming a significant issue. The hazardous effects of inadvertent exposure to bisphenol-releasing chemicals in professional workers and the general populations therefore deserve investigation.
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Cites
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Cited by
Rochester, J. R., & Bolden, A. L. (2015) · Environmental Health Perspectives · doi:10.1289/ehp.1408989 · Cited by 1,524
Blair, R. M. (2000) · Toxicological Sciences · doi:10.1093/toxsci/54.1.138 · Cited by 806
Meerts, I. A., Letcher, R. J., Hoving, S., Marsh, G., Bergman, A., Lemmen, J. G., van der Burg, B., & Brouwer, A. (2001) · Environmental Health Perspectives · doi:10.1289/ehp.01109399 · Cited by 732
Acute toxicity, mutagenicity, and estrogenicity of bisphenol‐A and other bisphenols
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Metadata
- Authors
- Perez, P., Pulgar, R., Olea-Serrano, F., Villalobos, M., Rivas, A., Metzler, M., Pedraza, V, & Olea, N.
- Venue
- Environmental Health Perspectives
- Publisher
- American Chemical Society (ACS)
- Published
- 1998-03
- Volume
- 106
- Issue
- 3
- Pages
- 167-174
- ISSN
- 0091-6765 (ISSN-L)
- 1552-9924
- OpenAlex
- W2087919607
- Cited by
- 254
- References
- 22
- FWCI
- 13.70
- Type
- journal article
- Language
- en
- Open access
- gold
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- Perez, P., Pulgar, R., Olea-Serrano, F., Villalobos, M., Rivas, A., Metzler, M., Pedraza, V, & Olea, N. (1998). The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups. Environmental Health Perspectives. https://doi.org/10.1289/ehp.98106167
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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