In vitro conversion of environmental estrogenic chemical bisphenol A to DNA binding metabolite(s) Article

Atkinson, A, Roy, D. (1995). In vitro conversion of environmental estrogenic chemical bisphenol A to DNA binding metabolite(s) . BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 210(2), 424-433. 10.1006/bbrc.1995.1678

cited authors

  • Atkinson, A; Roy, D

authors

abstract

  • In the present study we have investigated the ability of bisphenol A to be converted to reactive metabolite(s) and its potential to bind to DNA. In this in vitro study we show that bisphenol A is oxidized by 70% to bisphenol o-quinone. The evidence for the formation of bisphenol o-quinone was shown by UV, IR and GC-MS. The new product, bisphenol o-quinone, had a maximum UV absorption at 386 nM, the appearance of an IR characteristic of unsaturated carbonyl (1690 cm-1) and a mass of 242. The chemical reaction of deoxyguanosine monophosphate (dGMP) or DNA with bisphenol o-quinone produced 6-8 adducts. The in vitro incubation of DNA with bisphenol A in the presence of peroxidase activation system also produced one major and seven minor adducts. The chromatographic mobilities of major DNA adducts four and six formed by bisphenol A in the presence of peroxidase activation system closely matched those of spots four and six obtained by chemical reaction between DNA or dGMP with bisphenol o-quinone. Based on these data it appears that bisphenol A is converted to DNA binding metabolites in vitro. Whether irreversibile binding of bisphenol A to DNA through metabolic activation may be responsible for some of the toxic effects produced by bisphenol A is not clear. © 1995 by Academic Press, Inc.

publication date

  • January 1, 1995

published in

Digital Object Identifier (DOI)

start page

  • 424

end page

  • 433

volume

  • 210

issue

  • 2