Role of cytochrome P4501A1 in biotransformation of a tissue specific sarcomagen N-methyldibenzo[c,g]carbazole

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 469, Issue 2, 2000, Pages 259-269

  Gábelová, Alena ^a   Bačová, Gabriela ^a   Ružeková, L'ubica ^a   Farkašová, Timea ^a  

^a CANCER RESEARCH INSTITUTE   (Slovakia)

Author keywords

7H dibenzo c,g carbazole; DNA damage profile; DNA repair endonucleases; Hep G2 cells; N methyldibenzo c,g carbazole; Single cell gel electrophoresis; V79MZh1A1 cells

Indexed keywords

7H DIBENZOLE(C,G)CARBAZOLE; CYTOCHROME P450; ENDONUCLEASE; N METHYLDIBENZO[C,G] CARBAZOLE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOTRANSFORMATION; CARCINOGENESIS; CELL STRAIN V 79; CHO CELL; COMET ASSAY; CONTROLLED STUDY; DNA DAMAGE; DNA REPAIR; ENZYME ACTIVITY; METHODOLOGY; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; BIOTRANSFORMATION; CARBAZOLES; CARCINOGENS; CELL LINE; COLONY-FORMING UNITS ASSAY; CRICETINAE; CYTOCHROME P-450 CYP1A1; DNA DAMAGE; HUMANS; SARCOMA, EXPERIMENTAL;

CELL FUSING AGENT VIRUS;

EID: 0034692610     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5718(00)00087-5     Document Type: Article

References (50)

1. Dorbon M., Schmitter J.M., Arpino P., Guiochon G. Carbazoles et lactames du pétrole: méthode d'extraction et caractérisation. J. Chromatogr. 246:1982;255.
2. Van Duuren B.L., Bilbao J.A., Joseph C.A. The carcinogenic nitrogen heterocyclics in cigarette smoke condensate. J. Natl. Cancer Inst. 25:1960;53.
3. Van Duuren B.L. Separation and identification of aliphatic and aromatic carcinogens from environmental sources. Natl. Cancer Inst. Monogr. 9:1962;135.
4. Yu M.L., Hites R.A. Identification of organic compounds in diesel engine soot. Anal. Chem. 53:1981;951.
5. Tomatis L. The IARC program on the evaluation of the carcinogenic risk of chemicals to man. Ann. N.Y. Acad. Sci. 271:1976;396-409.
6. Ho C.-H., Clark B.R., Guerin M.R., Barkenbus B.D., Rao T.K., Epler J.L. Analytical and biological analysis of test materials from the synthetic fuel technologies. IV. Studies of the chemical structure-mutagenic activity relationships of aromatic nitrogen compounds relevant to synfuels. Mutat. Res. 85:1981;335-345.
7. W.R. West, P.A. Smith, P.W. Stoker, G.M. Booth, T. Smith-Oliver, B.E. Butterworth, M.L. Lee, Analysis and genotoxicity of a PAC-polluted river sediment, in: M. Cooke, A.J. Dennis (Eds.), Polynuclear Aromatic Hydrocarbons: Mechanism, Methods and Metabolism, Eighth International Symposium, Columbus, OH, Battelle Press, 1984, pp. 1395-1411.
8. Boyland E., Bruec A.M. The carcinogenic action of dibenzocarbazoles. Proc. R. Soc. London B. 122:1937;429.
9. Kirby A.H.M., Peacock P.R. The influence of methylation on carcinogenic activity. I. N-methyl-3:4:5:6-dibenzocarbazole. Br. J. Exp. Pathol. 27:1946;179-189.
10. Sellakumar A., Stenback F., Rowland J., Shubik P. Tumor induction by 7H-dibenzo[c,g]carbazole in the respiratory tract of Syrian hamsters. J. Toxicol. Environ. Health. 3:1977;935-939.
11. Bonser G.M., Crabbe J.G.S., Jull J.W. Induction of epithelial neoplasms in the urinary bladder of the dog by intravesical injection of a chemical carcinogen. J. Pathol. Bacteriol. 68:1954;561.
12. IARC, Monographs on the Evaluetion of the Carcinogenic Risks of Chemicals to Man: Certain Polycyclic Aromatic Hydrocarbons and Heterocyclic Compounds, Vol. 3, International Agency for Research on Cancer, Lyon, France, 1972.
13. IARC, Monographs on the Evaluation of the carcinogenic Risk of Chemicals to Man: Polynuclear Aromatic Compounds. Pt. 1. Chemical, Environmental and Experimental Data, Vol. 32, International Agency for Research on Cancer, Lyon. France, 1983.
14. Boffeta P., Jourenkova N., Gustavsson P. Cancer risk from occupational and environmental exposure to polycyclic aromatic hydrocarbons. Cancer Causes and Control. 8:1997;444-472.
15. Périn F., Dufour M., Mispelter J., Ekert B., Künnecke C., Oesch F., Zajdela F. Heterocyclic aromatic hydrocarbon carcinogenesis: 7H-dibenzo[c,g] carbazole metabolism by microsomal enzymes from mouse and rat liver. Chem. Biol. Interact. 35:1981;267-284.
16. Périn F., Valéro D., Mispelter J., Zajdela F. In vitro metabolism of N-methyldibenzo[c,g] carbazole a potent sarcomagen devoid of hepatotoxic and hepatocarcinogenic properties. Chem. Biol. Interact. 48:1984;281-295.
17. Valéro D., Périn F., Plessis M.-J., Zajdela F. Sexual differences in the expression of gamma-glutamyltranspeptidase during 5,9-dimethyl dibenzo[c,g] carbazole-induced hepatocarcinogenesis in mice. Cancer Lett. 27:1985;181-197.
18. Warshawsky D., Meyers B.L. The metabolism of 7H-dibenzo[c,g] carbazole, a N-heterocyclic aromatic in the isolated perfused lung. Cancer Lett. 12:1981;153-159.
19. Schurdak M.E., Stong D.B., Warshawsky D., Randerath K. N-methylation reduces the DNA-binding activity of 7H-dibenzo[c,g]carbazole ∼300-fold in mouse liver but only ∼2-fold in skin: possible correlation with carcinogenic activity. Carcinogenesis. 8:1987;1405-1410.
20. J.L. Hartwell, Survey of compounds which have been tested for carcinogenic activity, USPHS Publication, Vol. 149, 1951, pp. 478-479.
21. Stong D.B., Christian R.T., Jayasimhulu K., Wilson R.M., Warshawsky D. The chemistry and biology of 7H-dibenzo[c,g] carbazole: synthesis and characterization of selected derivatives, metabolism in rat liver preparation and mutagenesis mediated by cultured rat hepatocytes. Carcinogenesis. 10:1989;419-427.
22. Wan L.P., Xue W.L., Schneider J., Reilman R., Radike M., Warshawsky D. Comparative metabolism of 7H-dibenzo[c,g]carbazole and dibenzo[a,j] acridine by mouse and rat liver microsomes. Chem. Biol. Interact. 81:1992;131-147.
23. Chen L., Devanesan P.D., Byun J., Gooden J.K., Gross M.L., Rogan E.G., Cavalieri E.L. Synthesis of depurinating DNA adducts formed by one-electron oxidation of 7H-dibenzo[c,g]carbazole and identification of these adducts after activation with rat liver microsomes. Chem. Res. Toxicol. 10:1997;225-233.
24. Schurdak M.E., Randerath K. Tissue-specific DNA adduct formation in mice treated with the environmental carcinogen, 7H-dibenzo[c,g]carbazole. Carcinogenesis. 6:1985;1271-1274.
25. 32P Postlabeling analysis of DNA adduction in mice by synthetic metabolites of the environmental carcinogen, 7H-dibenzo[c,g]carbazole: chromatographic evidence for 3-hydroxy-7H-dibenzo[c,g]carbazole being a proximate genotoxicant in liver but not skin Carcinogenesis. 8:1987;591-597.
26. Parks W., Schurdak M.E., Randerath K., Maher V., McCormick J.J. Human cell-mediated cytotoxicity, mutagenicity, and DNA adduct formation of 7H-dibenzo[c,g]carbazole and its N-methyl derivative in diploid human fibroblasts. Cancer Res. 46:1986;4706-4711.
27. Gábelová A., Périn-Roussel O., Jounaidi Y., Périn F. DNA adduct formation in primary mouse embryo cells induced by 7H-dibenzo[c,g]carbazole and its organ-specific carcinogenic derivatives. Environ. Mol. Mutagen. 30:1997;56-64.
28. Renault D., Tombolan F., Brault D., Périn F., Thybaud V. Comparative mutagenicity of 7H-dibenzo[c,g]carbazole and two derivatives in Muta™ Mouse liver and skin. Mutat. Res. 417:1998;129-140.
29. Taras-Valéro D., Périn-Roussel O., Plessis M.-J., Périn F. Inhibition of 5,9,-dimethyldibenzo[c,g]carbazole-DNA adduct formation in mouse liver by pretreatment with cytochrome P4501A inducers in vivo. Environ. Mol. Mutagen. 32:1998;314-324.
30. Singh N.P., McCoy M.T., Tice R.R., Schneider E.L. A simple technique for quantification of low levels of DNA damage in individual cells. Exp. Cell Res. 175:1988;184-191.
31. Collins A.R., Duthie S.J., Dobson V.L. Direct enzymatic detection of endogenous base damage in human lymphocyte DNA. Carcinogenesis. 14:1993;1733-1735.
32. Slameňová D., Gábelová A., Ružeková L'., Chalupa I., Horváthová E., Farkašová T., Bozsakyová E., Štětina R. Detection of MNNG-induced DNA lesions in mammalian cells validation of comet assay against DNA unwinding technique, alkaline elution of DNA and chromosomal aberrations. Mutat. Res. 383:1997;243-252.
33. G. Ahnström, K. Erixon, Measurement of strand breaks by alkaline denaturation and hydroxyapatite chromatography, in: E.C. Friedberg, P.C. Hanawalt (Eds.), DNA Repair. A Laboratory Manual of Research Procedures, Marcel Dekker, New York, pp. 403-418.
34. Slameňová D., Budayová E., Gábelová A., Morávková A., Pániková L. Results of genetoxicity testing of mazindol (degonan), lithium carbonicum (contemnol) and dropropizine (ditustat) in Chinese hamster V79 and human EUE cells. Mutat. Res. 169:1986;171-177.
35. Szafarz D., Périn F., Valéro D., Zajdela F. Structure and carcinogenicity of dibenzo[c,g]carbazole derivatives. Biosci. Reports. 8:1988;633-643.
36. Périn-Roussel O., Périn F., Barat N., Plessis M.-J., Zajdela F. Interaction of 7H-dibenzo[c,g]carbazole and its organspecific derivatives with hepatic mitochondrial and nuclear DNA in the mouse. Environ. Mol. Mutagen. 25:1995;202-210.
37. Wilson N.M., Christou M., Turner C.R., Wrighton S.A., Jefcoate C.R. Binding and metabolism of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene by seven purified forms of cytochrome P-450. Carcinogenesis. 5:1984;1475.
38. Shimada T., Yun C.H., Yamazaki H., Gautier J.C., Beaune P.H., Guengerich F.P. Characterization of human lung microsomal cytochrome P-450 1A1 and its role in the oxidation of chemical carcinogens. Mol. Pharmacol. 41:1992;856.
39. Jacob J., Raab G., Soballa V., Schmalix W.A., Grimmer G., Greim H., Doehmer J., Seidel A. Cytochrome P450-mediated activation of phenanthrene in genetically engineered V79 Chinese hamster cells. Environ. Toxicol. Pharmacol. 1:1996;1-11.
40. Fuhr U., Doehmer J., Battula N., Wolfel C., Flick I., Kudla C., Keita Y., Staib A.H. Biotransformation of methylxanthines in mammalian cell lines genetically engineered for expression of single cytochrome P450 isoforms- allocation of metabolic pathways to isoforms and inhibitory effects of quinolones. Toxicology. 82:1993;169.
41. Jensen K.G., Onfelt A., Poulsen H.E., Doehmer J., Loft S. Effect of benzo[a]pyrene and (±)-trans-7,8-dihydro-7,8- dihydro-benzo[a]pyrene on mitosis in Chinese hamster V79 cells with stable expression of rat cytochrome P4501A1 or 1A2. Carcinogenesis. 14:1993;2115.
42. Gábelová A., Bačová G., Slameňová D., Périn F. Use of repair endonucleases for chracterization of DNA damage induced by N-heterocyclic aromatic hydrocarbons. Acta Biochim. Polonica. 45:1998;203-208.
43. Devanesan P., Higginbotham S., Ariese F., Jankowiak R., Suh M., Small G.J., Cavalieri E.L., Rogan E.G. Depurinating and stable benzo[a]pyrene-DNA adducts formed in isolated rat liver nuclei. Chem. Res. Toxicol. 9:1996;1113-1116.
44. O'Connor P., Fremont S., Schneider J., Dowty H., Jaeger M., Talaska G., Warshawsky D. Combination of high-performance liquid chromatography and thin-layer chromatography separation of five adducted nucleotides isolated from liver resulting from intraperitoneal administrarion with 7H-dibenzo[c,g]carbazole to mice. J. Chromatogr. B. 700:1997;49-57.
45. Epe B., Pflaum M., Häring M., Hegler J., Rüdiger H. Use of repair endonucleases to characterize DNA damage induced by reactive oxygen species in cellular and cell-free systems. Toxicol. Lett. 67:1993;57-72.
46. Hang B., Chenna A., Fraenkel-Conrat H., Singer B. An anusual mechanism for the major human apurinic/apyrimidinic (AP) endonuclease involving 5′ cleavage of DNA containing a benzene-derived exocyclic adduct in the absence of an AP sites. Proc. Natl. Acad. Sci. U. S. A. 93:1996;13737-13741.
47. Talaska G., Reilman R., Schamer M., Roh J.H., Xue W., Fremont S.L., Warshawsky D. Tissue distribution of DNA adducts of 7H-dibenzo[c,g]carbazole and its derivatives in mice following topical application. Chem. Res. Toxicol. 7:1994;374-379.
48. Meier J.R., Warshawsky D. Comparison of blood protein and target organ DNA and protein binding following topical application of benzo[a]pyrene and 7H-dibenzo[c,g]carbazole to mice. Carcinogenesis. 15:1994;2233-2240.
49. Schweikl H., Taylor J.A., Kitareewan S., Linko P., Nagornez D., Goldstein J.A. Expression of CYP1A1 and CYP1A2 genes in human liver. Pharmacogenetics. 3:1993;239-249.
50. Schmalix W.A., Mäser H., Kiefer F., Reen R., Wiebel F.J., Gonzalez F., Seidel A., Glatt H., Greim H., Doehmer J. Stable expression of human cytochrome P450 1A1 cDNA in V79 Chinese hamster cells and metabolic activation of benzo[a]pyrene. Eur. J. Pharmacol. Environ. Toxicol. Pharmacol. 248:1993;251-261.