Advisor Information
Dr. Douglas Stack
Location
Dr. C.C. and Mabel L. Criss Library
Presentation Type
Poster
Start Date
2-3-2018 9:00 AM
End Date
2-3-2018 10:15 AM
Abstract
Bisphenol-A (BPA) is a known endocrine-disrupting chemical and displays estrogenic properties. Both in vitro and in vivo studies have demonstrated BPA can display genotoxic properties. BPA is metabolized to catechols which are further oxidized to electrophilic o-quinones capable of binding to cellular nucleophiles. One hypothesis of BPA toxicity is reaction of these electrophilic metabolites with cellular nucleophiles. We have developed an efficient, high-yield synthesis of both mono- and di-o-quinones of BPA, in addition to mono- and dicatechols of BPA. We have investigated the products form when bisphenol A-3,4-quinone (BPA-3,4-Q) reacts with the sulfur nucleophiles N-acetylcysteine (NAS) and glutathione (GSH). The major and minor isomers are both the result of 1,6-conjugate addition and are produced almost instantly in high yield. Products were fully characterized by 1D- and 2-D NMR to distinguish 1,6- versus 1,4-addition isomers. We plan to use this model system to further explore the mechanism of adduct formation between sulfur nucleophiles and o-quinones and the resulting chemical properties of both NAC and GSH adducts.
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Conjugate addition of sulfur nucleophiles to bisphenol A-3,4-quinone
Dr. C.C. and Mabel L. Criss Library
Bisphenol-A (BPA) is a known endocrine-disrupting chemical and displays estrogenic properties. Both in vitro and in vivo studies have demonstrated BPA can display genotoxic properties. BPA is metabolized to catechols which are further oxidized to electrophilic o-quinones capable of binding to cellular nucleophiles. One hypothesis of BPA toxicity is reaction of these electrophilic metabolites with cellular nucleophiles. We have developed an efficient, high-yield synthesis of both mono- and di-o-quinones of BPA, in addition to mono- and dicatechols of BPA. We have investigated the products form when bisphenol A-3,4-quinone (BPA-3,4-Q) reacts with the sulfur nucleophiles N-acetylcysteine (NAS) and glutathione (GSH). The major and minor isomers are both the result of 1,6-conjugate addition and are produced almost instantly in high yield. Products were fully characterized by 1D- and 2-D NMR to distinguish 1,6- versus 1,4-addition isomers. We plan to use this model system to further explore the mechanism of adduct formation between sulfur nucleophiles and o-quinones and the resulting chemical properties of both NAC and GSH adducts.