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Estrogenic Activity of Styrene Oligomers after Metabolic Activation by Rat Liver Microsomes
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Estrogenic Activity of Styrene Oligomers after Metabolic Activation by Rat Liver Microsomes
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Journal Article
Estrogenic Activity of Styrene Oligomers after Metabolic Activation by Rat Liver Microsomes
2003
Overview
In this study we examined estrogenic activity of styrene oligomers after metabolic activation by rat liver microsomes. trans-1,2-Diphenylcyclobutane (TCB), cis-1,2-diphenylcyclobutane (CCB), 1,3-diphenylpropane, 2,4-diphenyl-1-butene, 2,4,6-triphenyl-1-hexene, and 1α-phenyl-4β-(1′-phenylethyl)tetralin were negative in the yeast estrogen screening assay and estrogen reporter assay using estrogen-responsive human breast cancer cell line MCF-7. However, TCB exhibited estrogenic activity after incubation with liver microsomes of phenobarbital-treated rats in the presence of reduced nicotinamide adenine dinucleotide phosphate (NADPH). Minor activity was observed when liver microsomes of untreated or 3-methylcholanthrene-treated rats were used instead of those from phenobarbital-treated rats. CCB, 1,3-diphenylpropane, and 2,4-diphenyl-1-butene also exhibited estrogenic activity after metabolic activation by liver microsomes, but the activity was lower than that of TCB. 2,4,6-Triphenyl-1-hexene and 1α-phenyl-4β-(1′-phenylethyl)tetralin did not show estrogenic activity after such incubation. When TCB was incubated with liver microsomes of phenobarbital-treated rats in the presence of NADPH, three metabolites were detected by high-performance liquid chromatography (HPLC). One metabolite isolated by HPLC exhibited a significant estrogenic activity. The active metabolite was identified as trans-1-(4-hydroxyphenyl)-2-phenylcyclobutane by mass and nuclear magnetic resonance spectral analysis. These results suggest that the estrogenic activity of TCB was caused by the formation of the 4-hydroxylated metabolite.
Publisher
National Institute of Environmental Health Sciences. National Institutes of Health. Department of Health, Education and Welfare,National Institute of Environmental Health Sciences
