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Please use this identifier to cite or link to this item: http://hdl.handle.net/10481/32450

Title: The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups
Authors: Pérez, Pilar
Pulgar Encinas, Rosa María
Olea Serrano, Fátima
Villalobos Torres, Mercedes
Rivas, A.
Metzler, Manfred
Pedraza Muriel, Vicente
Olea, Nicolás
Issue Date: 1998
Abstract: 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.
Sponsorship: This research was supported by grants from the Spanish Ministry of Health (FIS, 95/1959) and the Andalusian Regional Government Department of Health (Consejerla de Salud, 96/159).
Publisher: National Institute of Environmental Health
Description: This work was reported in part at the meeting Estrogens in the Environment IV: Linking Fundamental Knowledge, Risk Assessment, and Public Policy held in Washington, DC, 19-21 July 1997.
Keywords: Bisphenol-A
Bisphenol-F
Endocrine disrupting chemical
Hydroxylated diphenylalkanes
MCF7 breast cancer cells
Xenoestrogens
URI: http://hdl.handle.net/10481/32450
ISSN: 0091-6765
Rights : Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License
Citation: Pérez, P.; et al. The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups. Environmental Health Perspectives, 106(3): 167-174 (1998). [http://hdl.handle.net/10481/32450]
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