title: Chemical change of chlorinated bisphenol A by ultraviolet irradiation and cytotoxicity of their products on Jurkat cells.
abstract: Chlorinated derivatives of bisphenol A (ClBPAs) have been detected in wastewater from waste paper recycling plants. BPA and ClBPAs are always exposed to ultraviolet (UV) radiation in the environment and consequently various photoproducts might be produced. Acute cytotoxicity of photoproducts of BPA and ClBPAs are not known. In this study, we investigated the cytotoxicity and chemical structure of photoproducts of BPA and ClBPAs (3-chlorobisphenol A (3-ClBPA), 3,3'-dichlorobisphenol A (3,3'-diClBPA) and 3,3',5-trichlorobisphenol A (3,3',5-triClBPA)) after UV irradiation (UVA, UVB and UVC). The toxicities of photoproducts on Jurkat cells were determined by Alamar Blue assay, and the chemical structures of the photoproducts were identified using GC/MS. The cytotoxicities of 3-ClBPA and 3,3'-diClBPA were higher than that of BPA and 3,3',5-triClBPA. In addition, the toxicities of ClBPAs were increased by the irradiation of UVB and UVC at 100J/cm(2) and decreased at 1000J/cm(2) in comparison with those at 100J/cm(2), indicating that their structures had changed. 3-Hydroxybisphenol A (3-OHBPA) was detected in the photoproducts of 3-ClBPA irradiated with UVB and UVC at 100J/cm(2), and 3-OHBPA and 3-chloro-3'-hydroxybisphenol A (3-Cl-3'-OHBPA) were detected in those of 3,3'-diClBPA. However, these hydroxylated BPAs were not detected in the photoproducts exposed to 1000J/cm(2). The cytotoxicity of 3-OHBPA was the almost same as ClBPAs after UVB and UVC irradiation. These results indicate that the formation of hydroxylated BPAs might contribute to the increase in toxicity caused by UV irradiation.
authors.affiliation: Laboratory of Radiation Biology, Graduate School of Nutritional and Environmental Sciences, University of Shizuoka, 52-1 Yada, Shizuoka-shi 422-8526, Japan.
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Mutou
authors.forename: Yuko
authors.initials: Y
authors.lastname: Ibuki
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Terao
authors.forename: Shuji
authors.initials: S
authors.lastname: Kojima
authors.forename: Rensuke
authors.initials: R
authors.lastname: Goto