Benzo pyrene, metabolism

Daniel FB, Schut HAJ, Sandwisch DW, et al Interspecies comparisons of benzo[ ]pyrene metabolism and DNA-adduct formation in cultmed human and animal bladder and tracheobronchial tissues. Cancer Res MAI 2M 4729, 1983... 

Little PJ, MO James, JB Pritchard, JR Bend (1984) Benzo(a)pyrene metabolism in hepatic microsomes from feral and 3-methylcholanthrene-treated southern flounder, Paralichthys lethostigma. J Environ Pathol Toxicol Oncol 5 309-320. 

Livingstone DR, SV Farrar (1984) Tissue and subcellular distribution of enzyme activities of mixed-function oxygenase and benzo[a]pyrene metabolism in the common mussel Mytilis edulis L. Sci Tot Environ 39 209-235. 

Schoor, W.P. 1984. Benzo(a)pyrene metabolism in marine fish and some analytical aspects of its metabolites. Pages 391-396 in K.L. Hoover (ed.). Use of Small Fish in Carcinogenicity Testing. Natl. Cancer Inst. Mono. 65. Bethesda, MD. 

Schoor, W.P. and M. Srivastava, 1984. Position-specific induction of benzo[a]pyrene metabolism by 3-meth-ylcholanthrene and phenobarbital in mullet (Mugil cephalus), a marine fish. Comp. Biochem. Physiol. 73C 391-396. 

Smith, I.R., G.M. Kirby, H.W. Ferguson, and M.A. Hayes. 1993. Benzo[a]pyrene metabolism and excretion in white suckers with chronic liver diseases. Environ. Toxicol. Chem. 12 897-901. 

Miller, A.G., Israel, D. and Whitlock, J.P., Jr (1983) Biochemical and genetic analysis of variant mouse hepatoma cells defective in the induction of benzo(a) pyrene-metabolizing enzyme activity. 

Crouch LS, Ebel RE. 1987a. Benzo[a]pyrene metabolism in the Mongolian gerbil Influence of chlordecone and mirex induction. Xenobiotica 17(7) 859-67. 

Crouch LS, Ebel RE. 1987b. Influence of chlordecone and mirex exposure on benzo[a]pyrene metabolism of rat-liver microsomes. Xenobiotica 17 25-34. 

Fig. 10.13. Metabolism of benzo[ ]pyrene (10.34). Shown are stereoselective formation of three isomeric epoxides, EH-catalyzed, stereoselective hydration to the dihydrodiols 10.35, 10.36, and 10.37, and, finally, 9,10-epoxidation of 10.36 to the bay-region diol epoxide 10.38. The latter exists as...

Monteith DK, Novoting A, Michalopoulos G, Stron SC Metabolism of benzo[ ]pyrene in primary cultures of human hepatocytes Dose-response over a four-log range. Carcinogenesis 8 983-988, 1987... 

It is clear from these comments that the biochemical and toxicological effects seen after various inducers may be markedly different. This is illustrated by the effects of different inducers on the metabolism of various substrates examined in vitro and shown in Table 5.22. It can be seen that in some cases the inducers cause no change in the metabolism, whereas in other cases, metabolism is increased or even decreased. Thus studies in vitro showed that pretreatment with phenobarbital markedly increased benzphetamine metabolism but had no effect on benzo(a)pyrene metabolism. Conversely, 3-methylcholanthrene pretreatment increased benzo (a) pyrene metabolism but markedly decreased benzphetamine metabolism. 

Furman, G.M., Silverman, D.M. Schatz, R.A. (1991) The effect of toluene on rat lung benzo [a] pyrene metabolism and microsomal membrane lipids. Toxicology, 68, 75-87... 

Figure 12.12 Benzo[a]pyrene metabolism to the ultimate carcinogenic species. Heavy arrows indicate major metabolic pathways, represents ultimate carcinogenic species. (Adapted from A. H. Conney, Cancer Res. 42 4875, 1982.)...

Miller AG, Whitlock JP Jr. 1981. Novel variant in benzo [a] pyrene metabolism. J Biol Chem 256 2433-2437. 

Wheeler, E.L., Schwass, D.E., and Berry, D.L. Modulation of Benzo-a-pyrene Metabolism by Dietary Sulfur Amino Acids. 

Okano, P., J.P. Whitlock, Jr. (1980) Aryl Hydrocarbon Hydroxylase and Benzo-a-pyrene Metabolism in Rodent Liver and Human Cells. In Differentiation and Carcinogenesis in Liver Cell Cultures. C. Borek and G.M. Williams, eds. 

Modulation of Benzo[a]pyrene Metabolism by Dietary Sulfur Amino Acids... 

Wiebel, F.J., and Waters, H.L. Effect of Butylated Hydroxytoluene and Hydroxyanisole on Benzo(a)pyrene Metabolism and Binding. In J.R. Fouts and I. Gut (eds.). Industrial and Environmental Xenobiotics, pp. 258-260. Amsterdam Excerpta Medica, 1978. 

Dock, L., Cha, Y-N., Jernstrom, B., and Moldeus, P. Effect of 2(3)-tert-butyl-4-hydroxyanisole on benzo(a)pyrene Metabolism and NDA-binding of Benzo(a)pyrene Metabolites in Isolated Mouse Hepatocytes. Chem. Biol. Interact., 41 ... 

Gelboin. Differences in benzo(a)pyrene metabolism between rodent liver microsomes and embryonic cells. Cancer Res. 36 4476-4479, 1976. 

Shum, S., N.M. Jensen, and D.W. Nebert. The Murine Ah locus In utero toxicity and teratogenesis associated with genetic differences in benzo(a)pyrene metabolism. Teratology 20 365-376, 1979. 

Gelboin, H. (1980) Benzo[a]pyrene metabolism, activation, and carcinogenesis Role and regulation of mixed functional oxidases and related enzymes. Physiol. Rev. 60, 1107-1166. 

Capotorti, G., Digianvincenzo, P., Cesti, P., Bernard , A. GugUelmetti, G. (2004). Pyrene and benzo[a]pyrene metabolism by an Aspergillus terreiit strain isolated from a polycyclic aromatic hydrocarbons polluted soil. Biodegradation, 15, 79-85. 

Rats were treated with vehicle (control), phenobarbital (PB), or 3-methylcholanthrene (3-MC). Cytochrome P450, lipid, and reductase fractions were prepared and reconstituted. The reductase and lipid fractions were prepared from PB-treated rats. No hydroxylation activity was detected when hemoprotein was omitted from the reaction mixture. In Experiment 1, benzo[a]pyrene metabolism was measured by formation of fluorescent phenolic metabolites, and benzphetamine metabolism was measured by the rate of benzphetamine-dependent NADPH oxidation. In Experiment 2, the metabolism of pentobarbital, benzo[a]pyrene, and chlorcyclizine was measured by product formation. Experiment 1 was taken from Ref. (53) and Experiment 2 was taken from Ref. (55). 

An approach for determining the presence of multiple monooxygenases in rat liver microsomes was the use of chemicals that selectively affected certain monooxygenase activities but not others. For example, 7,8-benzoflavone (a-naphthoflavonc) markedly inhibited the hydroxylationofbenzo[a]pyrene by liver microsomes from 3-methylcholanthrene treated rats or by a cytochrome P448-dependent reconstituted enzyme system (68,69), but there was no effect or only a small stimulatory effect of 7,8-benzoflavone on benzo[a]pyrene metabolism in livers from untreated rats (68). 

Huang DY, Ohnishi T, Jiang H, Furukawa A, Ichikawa Y. 1999. Inhibition by retinoids of benzo(A)pyrene metabolism catalyzed by 3-methylcholanthrene-induced rat cytochrome P-450 1A1. Metabolism 48 689-92... 

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