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Reactivity of bisphenol A-3,4-quinone with DNA. A quantum chemical studyKolšek, Katra, farmacevtka ; Mavri, Janez ; Sollner Dolenc, MarijaBisphenol 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 depurinationSource: Toxicology in vitro. - ISSN 0887-2333 (Vol. 26, no. 1, 2012, str. 102-106)Type of material - article, component partPublish date - 2012Language - englishCOBISS.SI-ID - 3160945
Author
Kolšek, Katra, farmacevtka |
Mavri, Janez |
Sollner Dolenc, Marija
Topics
bisfenol A-3,4-quinone |
genotoksičnost |
kemija |
študije
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Database name | Field | Year |
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Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
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Kolšek, Katra, farmacevtka | 32321 |
Mavri, Janez | 08611 |
Sollner Dolenc, Marija | 08519 |
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