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Environ Toxicol Chem ; 27(2): 442-51, 2008 Feb.
Article in English | MEDLINE | ID: mdl-18348622

ABSTRACT

Compounds with stilbene structures are widely used as pharmaceuticals and personal care products (PPCPs) and are present in plants. A suite of stilbene-related compounds, including PPCPs and plant-derived compounds were tested in vitro for interactions with the human and rainbow trout estrogen receptors and in vivo with rainbow trout using vitellogenin levels as a biomarker. Among the compounds with antagonistic activity, the common structural similarity was (in addition to the stilbene backbone) the presence of 4-hydroxy substitution. Stilbene-related compounds found to act as inhibitors at the estrogen receptor included the plant-derived compound resveratrol and two formulations of fluorescent whitening agents used in detergents, 4,4'-bis(2-sulfostyryl)biphenyl and diaminostilbene-1. In the yeast estrogenicity screening assay, the concentrations which caused a 50% inhibition in estrogenic response (IC50s) with the human estrogen receptor ranged from 2.56 x 10(-6) to 2.56 x 10(-6) M. In the rainbow trout estrogen receptor assay, the IC50s ranged from 7.75 x 10(-8) to 1.11 x 10(-5) M. However, in the in vivo rainbow trout vitellogenin assay, tamoxifen was the only stilbene of the compounds tested to have a significant effect as an inhibitor of estrogenicity.


Subject(s)
Oncorhynchus mykiss/metabolism , Receptors, Estrogen/agonists , Receptors, Estrogen/antagonists & inhibitors , Stilbenes/pharmacology , Animals , Dose-Response Relationship, Drug , Environmental Pollutants/chemistry , Environmental Pollutants/pharmacology , Estradiol/pharmacology , Estrogen Receptor Modulators/chemistry , Estrogen Receptor Modulators/pharmacology , Female , Gene Expression Regulation , Humans , Molecular Structure , Stilbenes/chemistry , Vitellogenins/metabolism
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