Benzylic hydroxylation of 1-methylpyrene and 1-ethylpyrene by human and rat cytochromes P450 individually expressed in V79 Chinese hamster cells

Carcinogenesis

Volumn 20, Issue 9, 1999, Pages 1777-1785

  Engst, Wolfram ^b   Landsiedel, Robert ^b   Hermersdörfer, Heino ^b   Doehmer, Johannes ^a   Glatt, Hansruedi ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b GERMAN INSTITUTE OF HUMAN NUTRITION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL; CARBOXYLIC ACID DERIVATIVE; CARCINOGEN; CYTOCHROME P450; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE DERIVATIVE;

ANIMAL CELL; ARTICLE; BIOTRANSFORMATION; CELL STRAIN V 79; CONTROLLED STUDY; HYDROXYLATION; LIVER METABOLISM; LIVER MICROSOME; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; BIOTRANSFORMATION; CARCINOGENS, ENVIRONMENTAL; CELL LINE; CRICETINAE; CRICETULUS; CYTOCHROME P-450 ENZYME SYSTEM; ETHANOL; HUMANS; HYDROXYLATION; ISOENZYMES; LUNG; MICROSOMES, LIVER; PYRENES; RATS; RECOMBINANT FUSION PROTEINS; SPECIES SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032846314     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/20.9.1777     Document Type: Article

References (54)

1. IARC (1983) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Polynuclear Aromatic Compounds. Part 1. Chemicals, Environmental, and Experimental Data. Vol. 32. IARC Scientific Publications, IARC, Lyon.
2. IARC (1984) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Polynuclear Aromatic Compounds. Part 2. Carbon Blacks: Mineral Oils and some Nitroarenes. Vol. 33. IARC Scientific Publications, IARC, Lyon.
3. IARC (1984) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Polynuclear Aromatic Compounds. Part 3. Industrial Exposures in Aluminium Production, Coal Gasification, Coke Production, and Iron and Steel Founding. Vol. 34. IARC Scientific Publications, IARC, Lyon.
4. IARC (1985) IARC Monographs on the Evaluation on the Carcinogenic Risk of Chemicals to Humans. Polynuclear Aromatic Compounds. Part 4. Bitumens: Coal-Tars and Derived Products, Shale-Oils and Soots. Vol. 35. IARC Scientific Publications, IARC, Lyon.
5. IARC (1986) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Tobacco Smoking. Vol. 38. IARC Scientific Publications, IARC, Lyon.
6. Radke, M. (1987) Organic geochemistry of aromatic hydrocarbons. In Brooks, J. and Welte, D.H. (eds) Advances in Petroleum Geochemistry. Academic Press, London, UK, vol. 2, pp. 141-207.
7. Radke, M., Garrigues, P. and Willsch, H. (1990) Methylated dicyclic and tricyclic aromatic hydrocarbons in crude oils from the Handil field, Indonesia. Org. Geochem., 15, 17-34.
8. Schenck, P.A. and de Leeuw, J.W. (1982) Molecular organic geochemistry. In Hutzinger, O. (ed.) Handbook of Environmental Chemistry. Springer-Verlag, Berlin, vol. B/1B, pp. 111-129.
9. Rogge, W.R., Hildemann, L.M., Mazurek, M.A., Cass, G.R. and Simoneit, B.R.T. (1993) Sources of fine organic aerosol: 2. Noncatalyst and catalyst-equipped automobiles and heavy-duty diesel trucks. Environ. Sci. Technol., 27, 636-651.
10. Flesher, J.W., Myers, S.R. and Stansbury, K.H. (1990) The site of substitution of the methyl group in the bioalkylation of benzo[a]pyrene. Carcinogenesis, 11, 493-496.
11. Flesher, J.W., Myers, S.R. and Blake, J.W. (1986) Bioalkylation of polynuclear aromatic hydrocarbons: a predictor of carcinogenic activity. In Cooke, M. and Dennis, A.J. (eds) Polynuclear Aromatic Hydrocarbons: Chemistry, Characterization and Carcinogenesis. Battelle Press, Columbus, OH, pp. 271-284.
12. Jacob, J., Grimmer, G., Mohr, U., Emura, M., Riebe-Imre, M., Raab, G. and Knebel, J. (1993) Metabolic activation of chrysene and benzo[a]pyrene in hamster, rat and human in vitro lung cell cultures. Polycyclic Aromatic Comp., 3 (suppl.), 1175-1182.
13. Stansbury, K.H., Flesher, J.W. and Gupta, R.C. (1994) Mechanism of aralkyl-DNA adduct formation from benzo[a]pyrene in vivo. Chem. Res. Toxicol., 7, 254-259.
14. Glatt, H.R. and Oesch, F. (1986) Structural and metabolic parameters governing the mutagenicity of polycyclic aromatic hydrocarbons. In de Serres, F.J. (ed.) Chemical Mutagens: Principles and Methods for Their Detection. Plenum Press, New York, NY, vol. 10, pp. 73-127.
15. Thakker, D.R., Yagi, H., Levin, W., Wood, A.W., Conney, A.H. and Jerina, D.M. (1985) Polycyclic aromatic hydrocarbons: metabolic activation to ultimate carcinogens. In Anders, M.W. (ed.) Bioactivation of Foreign Compounds. Academic Press, Inc., pp. 177-242.
16. Watabe, T., Ishizuka, T., Isobe, M. and Ozawa, N. (1982) A 7-hydroxymethyl sulfate ester as an active metabolite of 7,12-dimethylbenz[a]anthracene. Science, 215, 403-405.
17. Miller, J.A. and Surh, Y.-J. (1994) Sulfonation in chemical carcinogenesis. In Kauffman, F.C. (ed.) Handbook of Pharmacology, Vol. 112, Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity. Springer-Verlag, Berlin, pp. 429-458.
18. Cavalieri, E., Roth, R. and Rogan, E. (1979) Hydroxylation and conjugation at the benzylic carbon atom: a possible mechanism of carcinogenic activation for some methyl-substituted aromatic hydrocarbons. In Jones, P.W. and Leber, P. (eds) Polynuclear Aromatic Hydrocarbons. Ann Arbor Science Publishers, Ann Arbor, MI, pp. 517-529.
19. Landsiedel, R., Engst, W., Seidel, A. and Glatt, H.R. (1996) Physico-chemical properties and mutagenicity of benzylic compounds. Exp. Toxicol. Pathol., 48 (Suppl. 2), 215-222.
20. Landsiedel, R., Engst, W., Scholtyssek, M., Seidel, A. and Glatt, H.R. (1996) Benzylic sulphuric acid esters react with diverse functional groups and often form secondary reactive species. Polycyclic Aromat. Comp., 11, 341-348.
21. Rice, J.E., Rivenson, A., Braley, J. and LaVoie, E.J. (1987) Methylated derivatives of pyrene and fluorene: evaluation of genotoxicity in the hepatocyte/DNA repair test and tumorigenic activity in newborn mice. J. Toxicol. Environ. Health, 21, 525-532.
22. 1 mice. Biochem. Biophys. Res. Commun., 172, 85-91.
23. Surh, Y.-J., Blomquist, J.C. and Miller, J.A. (1990) Activation of 1-hydroxymethylpyrene to an electrophilic and mutagenic metabolite by rat hepatic sulfotransferase activity. In Witmer, C.M., Snyder, R.R., Jollow, D.J., Kalf, G.F., Kocsis, J.J. and Sipes, I.G. (eds) Biological Reactive Intermediates IV: Molecular and Cellular Effects and Their Impact on Human Health. Plenum Press, New York, NY, pp. 383-391.
24. Glatt, H.R., Werle-Schneider, G., Enders, N., Monnerjann, S., Pudil, J., Czich, A., Seidel, A. and Schwarz, M. (1994) 1-Hydroxymethylpyrene and its sulfuric acid ester: toxicological effects in vitro and in vivo, and metabolic aspects. Chem. Biol. Interact., 92, 305-319.
25. Flesher, J.W., Horn, J. and Lehner, A.F. (1997) 6-Sulfooxymethylbenzo[a]pyrene is an ultimate electrophilic and carcinogenic form of the intermediary metabolite 6-hydroxymethylbenzo[a]pyrene. Biochem. Biophys. Res. Commun., 234, 554-558.
26. Flesher, J.W. and Sydnor, K.L. (1973) Possible role of 6-hydroxymethylbenzo[a]pyrene as a proximate carcinogen of benzo[a]pyrene and 6-methylbenzo[a]pyrene. Int. J. Cancer, 11, 433-437.
27. Conney, A.H., Chang, R.L., Jerina, D.M. and Wei, S.J.C. (1994) Studies on the metabolism of benzo[a]pyrene and dose-dependent differences in the mutagenic profile of its ultimate carcinogenic metabolite. Drug Metab. Rev., 26, 125-163.
28. Grimmer, G. (1988) Polycyclische aromatische Kohlenwasserstoffe. In Eisenbrand, G., Frank, H.K., Grimmer, G., Hapke, H.-J., Thier, H.-P. and Weigert, G. (eds) Derzeitige Belastung und Trends bei der Belastung der Lebensmittel durch Fremdstoffe. Verlag W. Kohlhammer GmbH, Karlsruhe, pp. 151-187.
29. Okamoto, H. and Yoshida, D. (1981) The isolation identification of mutation enhancing principles from cellulose pyrolysate. Agric. Biol. Chem., 45, 1291-1294.
30. Pancirov, R.J. and Brown, R.A. (1977) Polynuclear aromatic hydrocarbons in marine tissues. Environ. Sci. Technol., 11, 989-992.
31. Glatt, H.R., Pauly, K., Czich, A., Falany, J.L. and Falany, C.N. (1995) Activation of benzylic alcohols to mutagens by rat and human sulfotransferases expressed in Escherichia coli. Eur. J. Pharmacol., 293, 173-181.
32. Glatt, H.R. (1997) Bioactivation of mutagens via sulfation. FASEB J., 11, 314-321.
33. Glatt, H.R., Bartsch. I., Christoph, S., Coughtrie, M.W.H., Falany, C.N., Hagen, M., Landsiedel, R., Pabel, U., Phillips, D.H., Seidel, A. and Yamazoe, Y. (1998) Sulfotransferase-mediated activation of mutagens studied using heterologous expression systems. Chem. Biol. Interact., 109, 195-219.
34. Hagen, M., Pabel, U., Landsiedel, R., Bartsch, I. and Glatt, H.R. (1998) Expression of human estrogen sulfotransferase in Salmonella typhimurium: differences between hHST and hEST in the enantioselective activation of 1-hydroxyethylpyrene to a mutagen. Chem. Biol. Interact., 109, 249-253.
35. Rice, J.E., Geddie, N.G., DeFloria, M.C. and LaVoie, E.J. (1988) Structural requirements favoring mutagenic activity among methylated pyrenes in S. typhimurium. In Cooke, M. and Dennis, A. (eds) Polynuclear Aromatic Hydrocarbons: A Decade of Progress. Battelle Press, Columbus, OH, pp. 773-785.
36. 1. Proc. Natl Acad. Sci. USA, 85, 5769-5773.
37. Dogra, S., Doehmer, J., Glatt, H.R., Mölders, R., Siegert, P., Friedberg, T., Seidel, A. and Oesch, F. (1990) Stable expression of rat cytochrome P450IAl cDNA in V79 Chinese hamster cells and their use in mutagenicity testing. Mol. Pharmacol., 37, 608-613.
38. Glatt, H.R., Gemperlein, I., Setiabudi, F, Platt, K.-L. and Oesch, F. (1990) Expression of xenobiotic-metabolising enzymes in propagatable cell cultures and induction of micronuclei by 13 compounds. Mutagenesis, 5, 241-249.
39. Glatt, H.R., Hornhardt, S., Pauly, K., Piée-Staffa, A., Seidel, A. and Czich, A. (1994) Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures. Toxicol. Lett., 72, 13-21.
40. Autorenkollektiv (1988) Organikum. VEB Deutscher Verlag der Wissenschaften, Berlin.
41. Enders, N., Seidel, A., Monnerjahn, S. and Glatt, H.R. (1993) Synthesis of 11 benzylic sulfate esters, their bacterial mutagenicity and its modulation by chloride, bromide and acetate anions. Polycyclic Aromatic Comp., 3 (suppl.), 887-894.
42. Schneider, A., Schmalix, W.A., Siruguri, V., de Groene, E.M., Horbach, G.J., Kleingeist, B., Lang, D., Bocker, R., Belloc, C., Beaune, P., Greim, H. and Doehmer, J. (1996) Stable expression of human cytochrome P450 3A4 in conjunction with human NADPH-cytochrome P450 oxidoreductase in V79 Chinese hamster cells. Arch. Biochem. Biophys., 332, 295-304.
43. Schmalix, W.A., Barrenscheen, M., Landsiedel, R., Janzowski, C., Eisenbrand, G., Gonzalez, F., Eliasson, E., Ingelman-Sundberg, M., Perchermeier, M., Greim, H. and Doehmer, J. (1995) Stable expression of human cytochrome P450 2E1 in V79 Chinese hamster cells. Eur. J. Pharmacol., 293, 123-131.
44. Schmalix, W.A., Maser, H., Kiefer, F, Reen, R., Wiebel, F.J., Gonzalez, F., Seidel, A., Glatt, H.R., Greim, H. and Doehmer, J. (1993) Stable expression of human cytochrome P450 IA1 cDNA in V79 Chinese hamster cells and metabolic activation of benzo[a]pyrene. Eur. J. Pharmacol., 248, 251-261.
45. Wölfel, C., Heinrich-Hirsch, B., Schulz-Schalge, T., Seidel, A., Frank, H., Ramp, U., Wächter, F., Wiebel, F.J., Gonzalez, F., Greim, H. and Doehmer, J. (1992) Genetically engineered V79 Chinese hamster cells for stable expression of human cytochrome P450IA2. Eur. J. Pharmacol., 228, 95-102.
46. Luch, A., Coffing, S.L., Tang, Y.M., Schneider, A., Soballa, V., Greim, H., Jefcoate, C.R., Seidel, A., Greenlee, W.F, Baird, W.M. and Doehmer, J. (1998) Stable expression of human cytochrome P450 1B1 in V79 Chinese hamster cells and metabolically catalyzed DNA adduct formation of dibenzo[a,l]pyrene. Chem. Res. Toxicol., 11, 686-695.
47. Wölfel, C., Platt, K.-L., Dogra, S., Glatt, H.R., Wächter, F. and Doehmer, J. (1991) Stable expression of rat cytochrome P4501A2 cDNA and hydroxylation of 17b-estradiol and 2-aminofluorene in V79 Chinese hamster cells. Mol. Carcinog., 4, 489-498.
48. Schmalix, W.A., Lang, D., Schneider, A., Böcker, R., Greim, H., and Doehmer, J. (1996) Stable expression and co-expression of human cytochrome P450 oxidoreductase and CYP1A2 in V79 Chinese hamster cells: sensitivity to quinones and biotransformation of 7-alkoxyresorufin and triazines. Drug Metab. Dispos., 24, 1314-1319.
49. Bücker, M., Golan, M., Schmassmann, H.U., Glatt, H.R., Stasiecki, P. and Oesch, F. (1979) The epoxide hydratase inducer trans-stilbene oxide shifts the metabolic epoxidation of benzo[a]pyrene from the bay- to the K-region and reduces its mutagenicity. Mol. Pharmacol., 16, 656-666.
50. Koehl, W., Amin, S., Staretz, M.E., Ueng, Y.F., Yamazaki, H., Tateishi, T., Guengerich, F.P. and Hecht, S.S. (1996) Metabolism of 5-methylchrysene and 6-methylchrysene by human hepatic and pulmonary cytochrome P450 enzymes. Cancer Res., 56, 316-324.
51. Safa, B., Lee, C. and Riddick, D.S. (1997) Role of the aromatic hydrocarbon receptor in the suppression of cytochrome P450 2C11 by polycyclic aromatic hydrocarbons. Toxicol. Lett., 90, 163-175.
52. McMahon, R.E. and Sullivan, H.R. (1966) Microsomal hydroxylation of ethyl benzene: stereo-specifity and the effect of phenobarbital induction. Life Sci., 5, 921-926.
53. McKay, S., Farmer, P.B., Cary, P.D. and Grover, P.L. (1987) The metabolism of 7-ethylbenz[a]anthracene by rat liver microsomal preparations. Drug Metab. Dispos., 15, 682-694.
54. Glatt, H.R., Seidel, A., Harvey, R.G. and Coughtrie, M.W.H. (1994) Activation of benzylic alcohols to mutagens by human hepatic sulphotransferases. Mutagenesis, 9, 553-557.