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| - Epimerization and Stability of Two New cis-Benzo[a]pyrene Tetrolsby the Use of Liquid Chromatography−Fluorescence and MassSpectrometry
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| - Quantitative determination of the hydrolysis products from proteins and DNA gives valuable informationregarding the reactive metabolite that forms the protein and DNA adduct. Quantification of protein−benzo[a]pyrene (BP) adducts represents a more sensitive method than quantification of BP−DNA adducts.The aim of the present study was to identify two hydrolysis products from BP-derived protein adductsfound in vitro and in vivo in a previous study. Male Wistar rats were injected i.p. with BP, and serumalbumin was isolated and subjected to acid hydrolysis at 70 °C for 3 h. The hydrolysate was subjectedto LC separation, and fractions of the two unknown compounds were collected. The molecular massesof the two unknown compounds were in accordance with being tetrols as judged by LC electrospraymass spectrometry. The fragmentation patterns were characteristic of tetrols with formation of the molecularion and the loss of water molecules. In addition, the compounds were subjected to acid hydrolysis at 70°C with 0.1 M HCl for 3 h. We observed that two of the known tetrols epimerized to the two unknowntetrols and vice versa. This is probably a characteristic epimerization involving not only position C10−OH but also another site like position C7−OH. The in vivo findings of the two unknown adducts areprobably the result of the formation of BPDE III in the metabolism of BP. These two tetrols must thenhave the C7−OH and C8−OH groups in a cis position.
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