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(T/FF223) Estrogenicity of bisphenol-A chloroderivatives produced in chlorinated drinking water. Olea, N.1, Zafra, A.2, González-Casado, A.2, del Olmo, M.2, Fernández, J.3, Fernández, M.F.1, Vílchez, J.L.2, 1 2 3 ABSTRACT- Bisphenol A (BPA) is an estrogenic monomer widely used in the manufacture of epoxy and phenolic resins, polycarbonates, polyacrylates and corrosion-resistant unsaturated polyester-styrene resins. It may be found in a diverse range of products including the interior coatings of food cans and filters, water containers and dental composites and sealants. We present a method to identify BPA chlorinated derviatives in tap water using a micro liquid-liquid extraction. The different chlorinated BPA derivatives (2-5) were synthesized, isolated and identified. The structure of these compounds were unequivocally established by GC-MS, 1H-NMR, and 13C-NMR spectroscopy (Figure). The influence of different experimental parameters (pH, reaction time, chlorine concentration and presence of cationic and anionic species) was also established. The present study also investigated the estrogenicity of these chlorinated bisphenols in the E-Screen bioassay. The proliferative effect (PE) of chlorinated bisphenols was significantly greater than 1 for all the compounds tested. Chlorinated BPA with the lowest degree of chlorination showed the highest estrogenic potency. In comparison with the PE of estradiol, all the positive compounds showed a full to partial agonistic response that produced cell yields ranging from 85% of estradiol-induced yield for bisphenol-A to 30% for tetrachlorine bisphenol-A derivative (5). (1) R1 = R2 = R3 = R4 = H; (2) R1 = Cl, R2 = R3 = R4 = H; (3) R1 = R3 = Cl, R2 = R4 = H; (4) R1 = R2 = R3 = Cl, R4 = H; (5) R1 = R2 = R3 = R4 = Cl Chlorine bisphenols and lipophilic organochlorine pesticides bioaccumulate in human fatty tissue. Further research is required to assess the repercussions of these findings for human health. Key words: bisphenols, chlorine bisphenol-A, estrogens |
