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Microsomal metabolism of picene
K L Platt1, P Petrovic, A Seidel
1Institute of Toxicology, University of Mainz, F.R.G.
Chemico-Biological Interactions
|January 1, 1988
Summary
Picene, a polycyclic aromatic hydrocarbon, is not carcinogenic in animal studies. Its metabolism produces fewer reactive dihydrodiol epoxides compared to carcinogenic PAHs, explaining its lack of carcinogenicity.
Area of Science:
- Environmental Chemistry
- Toxicology
- Metabolism Studies
Background:
- Picene (a polycyclic aromatic hydrocarbon) is predicted carcinogenic by calculations, but not by animal studies.
- Investigating picene's metabolism may explain its lack of observed carcinogenicity.
Purpose of the Study:
- To identify picene's metabolites using rat liver microsomes.
- To compare picene's metabolic profile with carcinogenic polycyclic aromatic hydrocarbons.
Main Methods:
- Incubation of picene with Aroclor 1254-pretreated rat hepatic microsomal fraction.
- Separation of metabolites using reversed-phase high-performance liquid chromatography.
- Identification of metabolites via chromatographic and spectral properties (UV, mass spectrometry).
Main Results:
- Sixteen picene metabolites were identified, including trans-1,2-, -3,4-, -5,6-dihydrodiols and 2-, 4-phenols.
- 4-picenol (32.2%) and 1,2-dihydrodiol (16.7%) were major metabolites.
- Picene formed significantly fewer polar metabolites than benzo[a]pyrene and dibenz[a,h]anthracene.
Conclusions:
- Picene metabolism yields lower amounts of potentially carcinogenic dihydrodiol epoxides.
- Enzymatic inability to form sufficient dihydrodiol bay-region epoxides likely explains picene's lack of carcinogenicity.