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Biocompatibility of Hydroxylated Metabolites of BISGMA and BFDGE

¹ Schools of Pharmacy and Dentistry, University of Missouri, 2411 Holmes Street, Kansas City, MO 64108-2792; and
² Dept. of Veterinary Biomedical Sciences, University of Missouri, Columbia, MO, USA;

View larger version (26K): [in a new window]   Figure 1. Structures of BISGMA, BFDGE, metabolites, and respective ammoniated mass from LC/MS analyses. Finnigan TSQ-700 mass spectrometer, Digital Unix work station, Finnigan software ICIS ver. 8.3, HP 1100 binary pump, Perkin Elmer autosampler, and Eppendorf TC-50 column heater. Chromatographic separation was achieved on a Metachem pre-column filter, a 2 x 4 mm C18 guard column, and a 2 x 30 mm C18 3µ Luna analytical column by Phenomenex at 40°C. The MS ionization mode was positive electrospray. The manifold pressure was 2 x 10-6 torr. The ESI spray voltage was 4.5 kV, and the current was 10 µA. The capillary temperature was 200°C. The electron multiplier was set at 1600 V. The CID argon gas pressure was 1.7 mTorr, and the CID offset was -18.0 volts. The injection volume was 20 µL, and the split ratio was 1:3.

View larger version (18K): [in a new window]   Figure 2. Dose-response curves illustrate that the monomers BISGMA and BFDGE are more cytotoxic than their respective metabolites, BADPE-4OH and BFDPE-4OH. Cell survival was determined after L929 cell exposure to the test compounds for 20 hrs. Cell survival was indicated by metabolic conversion of the MTT reagent to formazan.

View larger version (18K): [in a new window]   Figure 3. Mutagenicity of bisphenol A diglycidyl ether (BFDGE) with and without liver S9 metabolism in strain TA100 of Salmonella typhimurium reverse-mutation assay. The tetrahydroxylated metabolite, BFDPE-4OH, was non-mutagenic.

View larger version (16K): [in a new window]   Figure 4. The monomer BFDGE, its metabolite BFDPE-4OH, and the hydroxylated metabolite BADPE-4OH did not stimulate MCF-7 cell proliferation. Estrogen-dependent cell proliferation was evaluated as total DNA per well. The half-maximal stimulation of cell proliferation by bisphenol A (BPA) was 150 nM. Values are expressed as percent of response between solvent control (approximately 0.55 µg DNA per well) and maximal response by estradiol (E2) at 0.1 nM (approximately 1.67 µg DNA per well).