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

Chemical Research in Toxicology

Volumn 10, Issue 2, 1997, Pages 225-233

  Chen, Liang ^a   Devanesan, Prabu D ^a   Byun, Jaeman ^b   Gooden, Jonathan K ^b   Gross, Michael L ^b   Rogan, Eleanor G ^a   Cavalieri, Ercole L ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; DNA;

ARTICLE; DNA ADDUCT; DNA BINDING; DNA DETERMINATION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MASS SPECTROMETRY; NONHUMAN; RAT;

ANIMALS; CARBAZOLES; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; ELECTRONS; IODINE; MAGNETIC RESONANCE SPECTROSCOPY; MICROSOMES, LIVER; OXIDATION-REDUCTION; RATS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

ARMORACIA RUSTICANA;

EID: 0031054836     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960149h     Document Type: Article

References (40)

1. Cavalieri, E. L., and Rogan, E. G. (1992) The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation. Pharmacol. Ther. 55, 183-199.
2. Cavalieri, E. L., and Rogan, E. G. (1995) Central role of radical cations in metabolic activation of polycyclic aromatic hydrocarbons. Xenobiotica 25, 677-688.
3. Sims, P., and Grover, P. L. (1981) Involvement of dihydrodiols and diol epoxides in the metabolic activation of polycyclic hydrocarbons other than benzo[a]pyrene. In Polycyclic Hydrocarbons and Cancer (Gelboin, H. V., and Ts'o, P. O. P., Eds.) pp 177-181, Academic Press, New York.
4. Conney, A. H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. Cancer Res. 42, 4875-4917.
5. Devanesan, P. D., RamaKrishna, N. V. S., Todorovic, R., Rogan, E. G., Cavalieri, E. L., Jeong, H., Jankowiak, R., and Small, G. J. (1992) Identification and quantitation of benzo[a]pyrene-DNA adducts formed by rat liver microsomes in vitro. Chem. Res. Toxicol. 5, 302-309.
6. Rogan, E. G., Devanesan, P. D., RamaKrishna, N. V. S., Higginbotham, S., Padmavathi, N. S., Chapman, K., Cavalieri, E. L., Jeong, H., Jankowiak, R., and Small, G. J. (1993) Identification and quantitation of benzo[a]pyrene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6, 356-363.
7. Chen, L., Devanesan, P. D., Higginbotham, S., Ariese, F., Jankowiak, R., Small, G. J., Rogan, E. G., and Cavalieri, E. L. (1996) Expanded analysis of benzo[a]pyrene-DNA adducts formed in vitro and in mouse skin: Their significance in tumor initiation. Chem. Res. Toxicol. 9, 897-903.
8. RamaKrishna, N. V. S., Devanesan, P. D., Rogan, E. G., Cavalieri, E. L., Jeong, H., Jankowiak, R., and Small, G. J. (1992) Mechanism of metabolic activation of the potent carcinogen 7,12-dimethylbenz[a]anthracene. Chem. Res. Toxicol. 5, 220-226.
9. Devanesan, P. D., RamaKrishna, N. V. S., Padmavathi, N. S., Higginbotham, S., Rogan, E. G., Cavalieri, E. L., Marsch, G. A., Jankowiak, R., and Small, G. J. (1993) Identification and quantitation of 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6, 364-371.
10. Li, K.-M., Todorovic, R., Rogan, E. G., Cavalieri, E. L., Ariese, F., Suh, M., Jankowiak, R., and Small, G. J. (1995) Identification and quantitation of dibenzo[a,l]pyrene-DNA adducts formed by rat liver microsomes in vitro: Preponderance of depurinating adducts. Biochemistry, 34, 8043-8049.
11. Chakravarti, D., Pelling, J. C., Cavalieri, E. L., and Rogan, E. G. (1995) Relating aromatic hydrocarbon-induced DNA adducts and c-Harvey-ras mutations in mouse skin papillomas: The role of apurinic sites. Proc. Natl. Acad. Sci. U.S.A. 92, 10422-10426.
12. Cremonesi, P., Rogan, E., and Cavalieri, E. (1992) Correlation studies of anodic peak potentials and ionization potentials for polycylic aromatic hydrocarbons. Chem. Res. Toxicol. 5, 346-355.
13. Van Duuren, B. L., Bilbao, J. A., and Joseph, C. A. (1960) The carcinogenic nitrogen heterocycles in cigarette smoke condensates. J. Natl. Cancer Inst. 25, 53-61.
14. Warshawsky, D., Talaska, G., Xue, W., and Schneider, J. (1996) Comparative carcinogenicity, metabolism, mutagenicity and DNA binding of 7H-dibenzo[c,g]carbazole and dibenz[a,j]acridine. Crit. Rev. Toxicol. 26, 213-249.
15. Warshawsky, D., Barkley, W., Miller, M. L., LaDow, K., and Andringa, A. (1994) Carcinogenicity of 7H-dibenzo[c,g]carbazole, dibenz[a,j]acridine and benzo[a]pyrene in mouse skin and liver following topical application. Toxicology 93, 135-149.
16. Warshawsky, D., Barkley, W., Miller, M. L., LaDow, K., and Andringa, A. (1992) Comparative tumor-initiating ability of 7H-dibenzo[c,g]carbazole and dibenz[a,j]acridine in mouse skin. Toxicology 71, 233-243.
17. NIH Guidelines for the Laboratory Use of Chemical Carcinogens (1981) NIH Publication No. 81-2385, U.S. Government Printing Office, Washington, DC.
18. Gross, M. L. (1990) Tandem mass spectrometry: Multisector magnetic instruments. In Methods in Enzymology, Vol. 193, Mass Spectrometry (McCloskey, J. A., Ed.) pp 131-153, Academic Press, San Diego.
19. Gross, M. L., Lyon, P. A., Chess, E. K., Crow, F. W., Evans, S., and Tudge, H. (1982) Triple analyzer mass spectrometry for high resolution MS/MS studies. Int. J. Mass Spectrom. Ion Phys. 42, 243-254.
20. Kaufmann, R., Kirsch, D., and Spengler, B. (1992) Fundamental aspects of post source decay in matrix-assisted laser desorption mass spectrometry. 1. Residual gas effects. J. Phys. Chem. 96, 9678-9684.
21. George, M., Wellemans, J. M. Y., Cerny, R. L., Gross, M. L., Li, K.-M., and Cavalieri, E. L. (1994) Matrix design for MALDI: Sensitive determination of PAH-DNA adducts. J. Am. Soc. Mass Spectrom. 5, 1021-1025.
22. Buu-Hoi, N. P., Hoan, N., and Khoi, N. H. (1949) Carcinogenic derivatives of carbazole. I. The synthesis of 1,2,7,8-, 1,2,5,6,-and 3,4,5,6-dibenzocarbazole and some of their derivatives. J. Org. Chem. 14, 492-497.
23. 32P-postlabeling analysis of benzo[a]pyrene-DNA adducts formed in vitro and vivo. Chem. Res. Toxicol. 2, 312-315.
24. RamaKrishna, N. V. S., Gao, F., Padmavathi, N. S., Cavalieri, E. L., Rogan, E. G, Cerny, R. L., and Gross M. L. (1992) Model adducts of benzo[a]pyrene and nucleosides formed from its radical cation and diol epoxide. Chem. Res. Toxicol. 5, 293-302.
25. RamaKrishna, N. V. S., Cavalieri, E. L., Rogan, E. G., Dolnikowski, G. G., Cerny, R. L., Gross, M. L., Jeong, H., Jankowiak, R., and Small, G. J. (1992) Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[a]-anthracene and deoxyribonucleosides formed by electrochemical oxidation: Models for metabolic activation by one-electron oxidation. J. Am. Chem. Soc. 114, 1863-1874.
26. RamaKrishna, N. V. S., Padmavathi, N. S., Cavalieri, E. L., Rogan, E. G., Cerny, R. L., and Gross, M. L. (1993) Synthesis and structure determination of the adducts formed by electrochemical oxidation of the potent carcinogen dibenzo[a,l]pyrene in the presence of nucleosides. Chem. Res. Toxicol. 6, 554-560.
27. Rochlitz, J. (1967) Neue Reaktionen der Carcinogen Kohlenwasserstoffe-II. Tetrahedron 23, 3043-3048.
28. Wilk, M., and Girke, W. (1972) Reactions between benz[a]pyrene and nucleobases by one-electron oxidation. J. Natl. Cancer Inst. 49, 1585-1597.
29. Cavalieri, E., and Auerbach, R. (1974) Reactions between activated benzo[a]pyrene and nucleophilic compounds with possible implications on the mechanism of tumor initiation. J. Natl. Cancer Inst. 53, 393-397.
30. Cavalieri, E., and Roth, R. (1976) Reaction of methylbenzanthracenes and pyridine by one-electron oxidation. A model for metabolic activation and binding of carcinogenic aromatic hydrocarbons. J. Org. Chem. 41, 2679-2684.
31. Cavalieri, E., and Rogan, E. (1985) Role of radical cations in aromatic hydrocarbon carcinogenesis. Environ. Health Perspect. 64, 69-84.
32. Rogan, E., Cavalieri, E., Tibbels, S., Cremonesi, P., Warner, C., Nagel, D., Tomer, K., Cerny, R., and Gross, M. (1988) Synthesis and identification of benzo[a]pyrene-guanine nucleoside adducts formed by electrochemical oxidation and horseradish peroxidase-catalyzed reaction of benzo[a]pyrene with DNA. J. Am. Chem. Soc. 110, 4023-4029.
33. Cerny, R., Wellemans, J. M. Y., George, M., and Gross, M. L. (1994) The use of tandem mass spectrometry for the structure determinatin of adducts formed between DNA and dibenzo[a,l]-pyrene. Polycycl. Aromat. Compd. 6, 215-222.
34. Gooden, J. K., Gross, M. L., Stack, D., Mulder, P., Li, K., and Cavalieri, E. L. (1995) MALDI-TOF analysis of steroid/PAH-modified DNA adducts at the femtomole level. Proceedings of the 43rd ASMS Conference on Mass Spectrometry and Allied Topics, Atlanta, GA, May 21-26, 1995.
35. Schurdak, M. E., and Randerath, K. (1985) Tissue specific DNA adduct formation in mice treated with the environmental carcinogen 7H-dibenzo[c,g]carbazole. Carcinogenesis 6, 1271-1274.
36. Schurdak, M. E., and Randerath, K. (1989) Effects of route of administration on tissue distribution of DNA adducts in mice: Comparison of 7H-dibenzo[c,g]carbazole, benzo[a]pyrene, and 2-acetylaminofluorene. Cancer Res. 49, 2633-2638.
37. Wan, L., Xue, W., Schneider, J., Reilman, R., Radike, M., and Warshawsky, D. (1992) Comparative metabolism of 7H-dibenzo[c,g]carbazole and dibenz[a,j]acridine by mouse and rat liver microsomes. Chem.-Biol. Interact. 81, 131-147.
38. Gill, J. H., Duke, C. C., Rosario, C. A., Ryan, A. J., and Holder, G. M. (1986) Dibenz[a,j]acridine metabolism: Identification of in vitro products formed by liver microsomes from 3-methylcholanthrene pretreated rats. Carcinogenesis 7, 1371-1378.
39. Schneider, J., Xue, W., and Warshawsky, D. (1994) Fluorescence spectroscopic studies on the identification and quantitation of metabolites of 7H-dibenzo[c,g]carbazole and dibenz[a,j]acridine. Chem.-Biol. Interact. 93, 139-153.
40. Gill, J. H., Duke, C. C., Ryan, A. J., and Holder, G. M. (1987) Dibenz[a,j]acridine: Distributions of metabolites formed by liver and lung microsomes from control and pretreated rats. Carcinogenesis 8, 425-431.