title: Change of estrogenic activity and release of chloride ion in chlorinated bisphenol a after exposure to ultraviolet B.
abstract: Bisphenol A (BPA) and chlorinated bisphenol A (ClBPAs) were detected in wastewater from waste paper recycling plants. In previous study, we showed the acute cytotoxicity of oxidized products of BPA and ClBPAs generated by ultraviolet (UV) irradiation. However, estrogenic activities of these photoproducts have not been studied. Therefore, we investigated change of estrogenic activities 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 UVB irradiation using yeast two-hybrid assay. The agonist activities of ClBPAs were higher than that of BPA in the absence of S9. ClBPAs irradiated with UVB lost agonist activities. The addition of S9 also completely erased the activity. The antagonist activities of BPA and ClBPAs with or without UVB irradiation were not detected both in the absence or presence of S9. UVB irradiation (0-100 J/cm2) decreased the agonist activity of 3,3'-diClBPA in proportion to increase of released chloride ion. The agonist activity was completely lost at 50 J/cm2 of UVB, of which dose could dissociated almost all chlorine. These findings suggested that UVB irradiation could decrease the estrogenic activity of chlorinated compounds, which was due to the selective release of chloride ion.
authors.affiliation: Laboratory of Radiation Biology, Graduate School of Nutritional and Environmental Sciences, University of Shizuoka, Shizuoka, Japan.
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Mutou
authors.forename: Yuko
authors.initials: Y
authors.lastname: Ibuki
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Terao
authors.forename: Shuji
authors.initials: S
authors.lastname: Kojima
authors.forename: Rensuke
authors.initials: R
authors.lastname: Goto
mesh_terms: D001559:Benzhydryl Compounds; D002712:Chlorides / Q000737:chemistry; D017606:Chlorine Compounds / Q000494:pharmacology / Q000528:radiation effects; D004307:Dose-Response Relationship, Radiation; D004965:Estrogen Antagonists / Q000494:pharmacology; D004968:Estrogens, Non-Steroidal / Q000494:pharmacology*; D010636:Phenols / Q000494:pharmacology* / Q000528:radiation effects*; D010782:Photolysis; D020798:Two-Hybrid System Techniques; D014466:Ultraviolet Rays; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D002712:Chlorides; D017606:Chlorine Compounds; D004965:Estrogen Antagonists; D004968:Estrogens, Non-Steroidal; D010636:Phenols; C006780:bisphenol A; D000098826:Bisphenol A Compounds