Reactivity of bisphenol A-3,4-quinone with DNA. A quantum chemical study

Kolšek, Katra (author), Mavri, Janez (author), Sollner Dolenc, Marija (author)

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 23.1 kcal/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 22.5 kcal/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

• Language: English
• Keywords: bisfenol A-3, 4-quinone, genotoksičnost, kemija, študije
• Work type: Not categorized (r6)
• Tipology: 1.01 - Original Scientific Article
• Organization: FFA - Faculty of Pharmacy
• Year: 2012
• Number of pages: str. 102-106
• Numbering: Vol. 26, no. 1
• UDC: 543.9+615.9
• ISSN on article: 0887-2333
• DOI: 10.1016/j.tiv.2011.11.003
• COBISS.SI-ID: 3160945
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Record is a part of a journal

• Title: Toxicology in vitro
• Shortened title: Toxicol. in vitro
• Publisher: Pergamon
• ISSN: 0887-2333
• COBISS.SI-ID: 25596165