The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups

Environmental Health Perspectives
P PerezN Olea

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 human...Continue Reading

References

May 1, 1991·Environmental Health Perspectives·A M SotoC Sonnenschein
Sep 1, 1990·Contact Dermatitis·R JolankiM L Henriks-Eckerman
Jul 4, 1990·Journal of the National Cancer Institute·P SkehanM R Boyd
May 1, 1987·Fundamental and Applied Toxicology : Official Journal of the Society of Toxicology·R E MorrisseyC A Kimmel
Jul 1, 1985·Journal of Steroid Biochemistry·A M Soto, C Sonnenschein
Sep 1, 1995·Environmental Health Perspectives·M VillalobosV Pedraza
Jun 1, 1995·Environmental Health Perspectives·J A BrotonsN Olea
Jan 1, 1995·Toxicology and Applied Pharmacology·A M Cummings, J L Metcalf
Oct 1, 1993·Environmental Health Perspectives·T ColbornA M Soto
Oct 1, 1995·Environmental Health Perspectives·A M SotoF O Serrano
Mar 1, 1996·Environmental Health Perspectives·N OleaC Sonnenschein
Feb 7, 1997·The Journal of Biological Chemistry·E J Routledge, J P Sumpter
May 1, 1997·Endocrinology·D Feldman
Jan 1, 1997·The Journal of Steroid Biochemistry and Molecular Biology·J B Colerangle, D Roy
Apr 1, 1959·British Journal of Industrial Medicine·L B BOURNEK B ALBERMAN

❮ Previous
Next ❯

Citations

Mar 20, 2013·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·J Hernandez-ElizondoM Mariscal-Arcas
May 15, 2010·Journal of Atherosclerosis and Thrombosis·Teruki KidaniHiroshi Masuno
May 7, 1999·Environmental Health Perspectives·H R AndersenA M Soto
Nov 9, 2004·Environmental Health Perspectives·Josephine G LemmenBart van der Burg
Nov 7, 2002·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·H NakazawaT Makino
Apr 28, 2004·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·T StrohekerM C Chagnon
Apr 28, 2004·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·K SatohF Nagai
Jun 8, 2006·Archives of Pharmacal Research·Seung Min OhKyu Hyuck Chung
Mar 21, 2007·Archives of Pharmacal Research·Seung Min OhKyu Hyuck Chung
Jan 6, 2006·Archives of Pharmacal Research·Soo Yeun LeeKyu Hyuck Chung
Jun 30, 2001·APMIS : Acta Pathologica, Microbiologica, Et Immunologica Scandinavica·A RivasN Olea
May 18, 2005·Food Additives and Contaminants·B M Thomson, P R Grounds
Dec 14, 2006·Food Additives and Contaminants·M-J Lopez-EspinosaN Olea
Aug 1, 2002·Environmental Toxicology and Pharmacology·Ryoko Kuruto-NiwaRyushi Nozawa
Jan 12, 2008·Journal of Toxicology and Environmental Health. Part B, Critical Reviews·Calvin C WillhiteClifton J McLellan
Oct 25, 2002·Toxicology in Vitro : an International Journal Published in Association with BIBRA·M ShimizuS Ozawa
Nov 20, 2012·Journal of Hazardous Materials·Kunlun ZhangGang Yu
Jun 15, 2011·Dental Materials : Official Publication of the Academy of Dental Materials·K L Van LanduytB Van Meerbeek
Aug 6, 2009·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Seung Min OhKyu Hyuck Chung
Jan 6, 2009·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·M Mariscal-ArcasF Olea-Serrano
Aug 2, 2008·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Nicolas CabatonElisabeth Perdu
Sep 5, 2007·Journal of Environmental Management·Isil Gültekin, Nilsun H Ince
Aug 11, 2007·Reproductive Toxicology·M F FernandezN Olea
Sep 17, 2016·Toxicological Sciences : an Official Journal of the Society of Toxicology·Shenxuan LiangXiaozhong Yu
Jul 1, 2015·Neurotoxicology·Vicente MustielesMariana F Fernández

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

© 2021 Meta ULC. All rights reserved