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SELECTIVE IN VITRO HORMONE ACTIVITY OF O,P'-DDT AND O,P'-METHOXYCHLOR OPTICAL ISOMERS
Citation:
Wiese, T. E., A W. Garrison, S. Nehls, AND T. C. Bishop. SELECTIVE IN VITRO HORMONE ACTIVITY OF O,P'-DDT AND O,P'-METHOXYCHLOR OPTICAL ISOMERS. Presented at 218th American Chemical Society National Meeting, New Orleans, LA, August 22-26, 1999.
Description:
Components and metabolites of the pesticides DDT and Methoxychlor have been described as endocrine disrupting chemicals with estrogen and/or antiandrogen activity. We account the estrogen and antiandrogen activity of the individual enantiomers of o,p'-DDT and o,p'-Methoxychlor. Optically pure samples (separated enantiomers) as well as racemic mixtures were evaluated for steroid receptor binding as well as hormone dependant proliferation and reporter gene activity in mammalian cells. The R(-) enantiomer of o,p'-DDT displayed enhanced estrogen receptor binding activity and was found be significantly more potent in estrogen dependant reporter and proliferation assays than the S(+). While both optical isomers of o,p'-Methoxychlor induced only minimal estrogen activity, an enantiomer selective antiandrogen capacity was observed. This study highlights the importance of resolving the enantiomers of chiral compounds for both endocrine disruptor characterization studies as well as environmental monitoring. Furthermore, we propose that the enantioselectivity of chiral compounds may be utilized to develop optically pure industrial chemicals with minimal endocrine activity.