title: Reactivity of bisphenol A-3,4-quinone with DNA. A quantum chemical study.
abstract: Bisphenol A is a primary component of polycarbonate plastics found in many different products - from reusable drink bottles to cell phones. It is also an important component of epoxy resins, which serve as a protective layer inside food and drink cans. Chronic exposure to bisphenol A from food, drink and other sources is the reason that this chemical shows up at low levels in the urine of nearly everyone. Bisphenol A is a known endocrine disruptor with a variety of other effects, including genotoxicity. These facts have created a lot of concern about how toxic it is. To investigate the possible genotoxic mechanisms of bisphenol A we calculated the chemical reactivity of the bisphenol A metabolite bisphenol A-3,4-quinone with deoxyguanosine by using density functional theory in conjunction with Langevin dipoles solvation model. The calculated activation free energy of 23.1kcal/mol shows that bisphenol A-3,4-quinone could form an adduct with deoxyguanosine and could be a mutagen. The subsequent depurination reaction was also studied with the same methodology. The calculated activation energy was 22.5kcal/mol, providing evidence that the rate-limiting step essential to causing genotoxicity is nucleophilic addition of the N7-deoxyguanosine to bisphenol A-3,4-quinone rather than depurination.
authors: Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000 Ljubljana, Slovenia.
authors: Katra
authors: K
authors: Kolšek
authors: Janez
authors: J
authors: Mavri
authors: Marija
authors: M
authors: Sollner Dolenc
mesh_terms: D001559:Benzhydryl Compounds; D016227:Benzoquinones / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D018736:DNA Adducts; D008956:Models, Chemical; D009153:Mutagens / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D016227:Benzoquinones; D004247:DNA; D018736:DNA Adducts; D009153:Mutagens; D010636:Phenols; C487806:bisphenol A 3,4-quinone; D000098826:Bisphenol A Compounds