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Epimerization and stability of two new cis-benzo(a)pyrene tetrols by the use of liquid chromatography-fluorescence and mass spectrometry

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  • 2006

Quantitative determination of the hydrolysis products from proteins and DNA gives valuable information regarding 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 adducts found in vitro and in vivo in a previous study. Male Wistar rats were injected i.p. with BP, and serum albumin was isolated and subjected to acid hydrolysis at 70 °C for 3 h. The hydrolysate was subjected to LC separation, and fractions of the two unknown compounds were collected. The molecular masses of the two unknown compounds were in accordance with being tetrols as judged by LC electrospray mass spectrometry. The fragmentation patterns were characteristic of tetrols with formation of the molecular ion 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 unknown tetrols and vice versa. This is probably a characteristic epimerization involving not only position C10−OH but also another site like position C7−OH. The...

Sagredo, Carlos Alberto Escobar; Olsen, Raymond; Greibrokk, Tyge; Molander, Pål; Øvrebø, Steinar
Chemical Research in Toxicology ACS Publications, Chemical Research in Toxicology 19: 392–398
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