Synthesis and identification of major metabolites of environmental pollutant dibenzo(c,mno)chrysene
- Penn State University, Hershey, PA (United States)
Dibenzo(c,mno)chrysene commonly known as naphtho(1,2-alpha}pyrene (N(1,2-alpha)P) is an environmental pollutant, recently identified in coal tar extract, in air-borne particulate matter, in marine sediment, and in cigarette-smoke condensate. We recently reported an efficient synthesis of N(1,2-alpha)P and examined its in vitro metabolism by male Sprague Dawley rat liver S9 fraction, which resulted in a number of dihydrodiol and phenolic metabolites. The synthesis of 10-hydroxy-N(1,2-alpha)P and fjord region N(1,2-alpha)P trans-9,10-dihydrodiol, which were identified among the various metabolites, was assigned earlier by comparing with the synthetic standards. The other major metabolites were separated by HPLC and, based on the {sup -1}H NMR analysis, were tentatively suggested to be the two K-region dibydrodiols, that is, N(1,2-alpha)P trans-4,5dihydrodiol and N(1,2-alpha)P trans-7,8-dihydrodiol, and the hydroxy derivatives of N(1,2-alpha)P. To unequivocally assign the structure to each of the peaks and to have them in larger amounts for toxicological studies, we have now synthesized the two K-region dihydrodiols and the 1-/3-hydroxy-N(1,2-alpha)P, short-listed based on the proton NMR of the collected peaks. As expected, all the synthesized dihydrodiol and phenolic derivatives of N(1,2-a)P identified with those obtained from in vitro metabolism enabling the assignment of all the major metabolites.
- OSTI ID:
- 20674599
- Journal Information:
- Chemical Research in Toxicology, Vol. 18, Issue 9; ISSN 0893-228X
- Country of Publication:
- United States
- Language:
- English
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