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Estrogenicity of selected biphenyls evaluated using a recombinant yeast assay
Author(s) -
Schultz T. Wayne,
Kraut Daniel H.,
Sayler Gary S.,
Layton Alice C.
Publication year - 1998
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620170912
Subject(s) - biphenyl , yeast , ring (chemistry) , chemistry , saccharomyces cerevisiae , stereochemistry , recombinant dna , ligand (biochemistry) , potency , ligand binding assay , biochemistry , receptor , organic chemistry , in vitro , gene
The estrogenic activity of biphenyl and 4‐hydroxylatedderivatives with varied levels of chloro‐ and/or hydroxyl substitution was measured in a Saccharomyces cerevisiae ‐based lac‐Z (β‐galactosidase) reporter assay. β‐Galactosidase activity was compared with competitive binding to soluble mouse uterine estrogen receptor protein. The comparison of relative potency for biphenyls hydroxylated on one ring and chlorinated on the other ring ( n = 5) revealed excellent correlation between the two systems ( r 2 = 0.995). However, estrogenicities of biphenyls hydroxylated and chlorinated on the same ring were not in agreement. Although weak ligand binding was demonstrated for these compounds, β‐galactosidase activity was not observed. Rather, these compounds were shown to be cytotoxic to yeast. The results of this study further support the hypothesis that both an unhindered phenolic ring and molecular symmetry are structural features associated with estrogenicity.