Laboratory of Radiation Biology, Graduate School of Nutritional and Environmental Sciences, University of Shizuoka, 52-1 Yada, Shizuoka-shi 422-8526, Japan.
Environ Toxicol Pharmacol. 2006 May;21(3):283-9. doi: 10.1016/j.etap.2005.09.005. Epub 2005 Nov 14.
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.
双酚 A 的氯化衍生物（ClBPAs）已在废纸回收厂的废水中被检出。BPA 和 ClBPAs 总是在环境中暴露于紫外（UV）辐射下，因此可能会产生各种光产物。BPA 和 ClBPAs 光产物的急性细胞毒性尚不清楚。在这项研究中，我们研究了 BPA 和 ClBPAs（3-氯双酚 A（3-ClBPA）、3,3'-二氯双酚 A（3,3'-diClBPA）和 3,3',5-三氯双酚 A（3,3',5-triClBPA））经紫外线（UVA、UVB 和 UVC）辐照后的细胞毒性和化学结构。通过 Alamar Blue 测定法测定光产物对 Jurkat 细胞的毒性，并用 GC/MS 鉴定光产物的化学结构。3-ClBPA 和 3,3'-diClBPA 的细胞毒性高于 BPA 和 3,3',5-triClBPA。此外，与 100J/cm(2)相比，ClBPAs 在 100J/cm(2)和 1000J/cm(2)下经 UVB 和 UVC 辐照后毒性增加，而在 1000J/cm(2)下毒性降低，表明其结构发生了变化。在 3-ClBPA 经 UVB 和 UVC 辐照于 100J/cm(2)后的光产物中检测到 3-羟基双酚 A（3-OHBPA），在 3,3'-diClBPA 的光产物中检测到 3-OHBPA 和 3-氯-3'-羟基双酚 A（3-Cl-3'-OHBPA）。然而，这些羟基化的 BPA 并未在暴露于 1000J/cm(2)的光产物中检出。3-OHBPA 在经 UVB 和 UVC 辐照后的细胞毒性与 ClBPAs 几乎相同。这些结果表明，羟基化 BPA 的形成可能导致 UV 照射引起的毒性增加。
