18-Aminoguanine: A Base Modification Produced in Rat Liver Nucleic Acids by the Hepatocarcinogen 2-Nitropropane

Chemical Research in Toxicology

Volumn 6, Issue 3, 1993, Pages 269-276

  Sodum, Rama S ^a   Nie, Guo ^a   Fiala, Emerich S ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROPROPANE; GUANINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BASE MISPAIRING; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER CARCINOGENESIS; LIVER METABOLISM; MALE; NONHUMAN; RAT;

ANIMALIA;

EID: 0027299698     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx00033a004     Document Type: Article

References (36)

1. International Agency for Research on Cancer (1982) IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man, Some Industrial Chemicals and Dyestuffs, Vol. 29, pp 331–343, WHO, Lyon, France.
2. Hoffmann, D. H., and Rathkamp, G. (1968) Chemical studies on tobacco smoke. III. Primary and secondary nitroalkanes in cigarette smoke. Beitr. Tabakforsch, 4, 124–134.
3. Lewis, T. R., Ulrich, C. E., and Busey, W. M. (1979) Subchronic inhalation toxicity of nitromethane and 2-nitropropane. J. Environ. Pathol. Toxicol. 2, 233–249.
4. Fiala, E. S., Czerniak, R., Castonguay, A., Conaway, C. C., and Rivenson, A. (1987) Assay of 1-nitropropane, 2-nitropropane, 1-azoxypropane, and 2-azoxypropane for carcinogenicity by gavage in Sprague-Dawley rats. Carcinogenesis 8, 1947–1949.
5. Fiala, E. S., Conaway, C. C., Mathis, J. E. (1989) Oxidative DNA and RNA damage in the livers of Sprague-Dawley rats treated with the hepatocarcinogen 2-nitropropane. Cancer Res. 49, 5518–5522.
6. Hussain, N. S., Conaway, C. C., Guo, N., Wagdy, A., and Fiala, E. S. (1990) Oxidative DNA and RNA damage in rat liver due to acetoxime: similarity to effects of 2-nitropropane. Carcinogenesis 11, 1013–1016.
7. Guo, N., Conaway, C. C., Hussain, N. S., and Fiala, E. S. (1990) Sex and organ differences in oxidative DNA and RNA damage due to treatment of Sprague-Dawley rats with acetoxime or 2-nitropropane. Carcinogenesis 11, 1659–1662.
8. Conaway, C. C., Guo, N., Hussain, N. S., and Fiala, E. S. (1991) Comparison of oxidative damage to rat liver DNA and RNA by primary nitroalkanes, secondary nitroalkanes, cyclopentanone oxime, and related compounds. Cancer Res. 51, 3143–3147.
9. National Research Council (1981) Selected Aliphatic Amines and Related Compounds: An Assessment of the Biological and Environmental Effects, pp 143–168, National Academy Press, Washington, DC.
10. Mirvish, S. S., Salmasi, S., and Runge, R. G. (1982) Carcinogenicity test of acetoxime in MRC-Wistar rats. J. Natl. Cancer Inst. 69, 961–962.
11. Conaway, C. C., Hussain, N. S., Way, B. M., and Fiala, E. S. (1991) Evaluation of secondary nitroalkanes, their nitronates, primary nitroalkanes, nitrocarbinols, and other aliphatic nitrocompounds in the Ames Salmonella assay. Mutat. Res. 261, 197–207.
12. Andrae, U., Homfeldt, H., Vogl, L., Lichtmannegger, J., and Summer, K. H. (1988) 2-Nitropropane induces DNA repair synthesis in rat hepatocytes in vitro and in vivo. Carcinogenesis 9, 811–815.
13. 7 position. Proc. Natl. Acad. Sci. U.S.A. 89, 8278–8282.
14. Long, R. A., Robins, R. K., and Townsend, L. B. (1967) Purine nucleosides. XV. The synthesis of 8-amino- and 8-substituted aminopurine nucleosides. J. Org. Chem. 32, 2751–2756.
15. 15N nuclear magnetic resonance studies on the tautomerism of 8-hydroxy-2′-deoxyguanosine, 8-hydroxyguanosine, and other C8-substituted guanine nucleosides. Chem. Res. Toxicol. 3, 445–452.
16. Kasai, H., and Nishimura, S. (1984) Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 12, 2137–2145.
17. Marmur, J. (1961) A procedure for the isolation of deoxyribonucleic acid from microorganisms. J. Mol. Biol. 3, 208–218.
18. Chomczynski, P., and Sacchi, N. (1987) Single-step method of RNA isolation by guanidinium thiocyanate–phenol–chloroform extraction. Anal. Biochem. 162, 156–159.
19. Kawazoe, Y., and Huang, G.-F. (1972) Direct C-amination of guanosine with hydroxylamine-O-sulfonic acid. Simplest model reaction possibly involved in DNA damage leading to carcinogenesis by N-arylhydroxylamines. Chem. Pharm. Bull. 20, 2073–2074.
20. Broom, A. D., and Robins, R. K. (1969) Purine nucleosides. XXIII. Direct amination of purine nucleosides. J. Org. Chem. 34, 1025–1029.
21. Sakurai, H., Hermann, G., Ruff, H. H., and Ullrich, V. (1980) The interaction of aliphatic nitro compounds with the liver microsomal monooxygenase system. Biochem. Pharmacol. 29, 341–345.
22. Ullrich, V., Hermann, G., and Weber, P. (1978) Nitrite formation from 2-nitropropane by microsomal monoxygenases. Biochem. Pharmacol. 27, 2301–2304.
23. Marker, E. K., and Kulkarni, A. P. (1985) Enzymatic denitrification of 2-nitropropane in uninduced mouse liver microsomes. Toxicol. Lett. 26, 181–185.
24. Russell, G. A. (1954) The autoxidation of 2-nitropropane in basic solution. J. Am. Chem. Soc. 76, 1595–1601.
25. Kido, T., and Soda, K. (1984) Oxidation of anionic nitroalkanes by flavoenzymes, and participation of superoxide anion in the catalysis. Arch. Biochem. Biophys. 234, 468–475.
26. DeRycker, J., and Halliwell, B. (1978) Oxidation of 2-nitropropane by horseradish peroxidase. Biochem. J. 175, 601–606.
27. Porter, D. J., and Bright, H. J. (1983) The mechanism of oxidation of nitroalkanes by horseradish peroxidase. J. Biol. Chem. 258, 9913–9924.
28. Kohda, K., Tada, M., Kasai, H., Nishimura, S., and Kawazoe, Y. (1986) Formation of 8-hydroxyguanine residues in cellular DNA exposed to the carcinogen 4-nitroquinoline-l-oxide. Biochem. Biophys. Res. Commun. 139, 626–632.
29. Floyd, R. A., West, M. S., Eneff, K. L., and Schneider, J. E. (1990) Mediation of 8-hydroxy-guanine formation in DNA by thiazin dyes plus light. Free Radical Biol. Med. 8, 327–330.
30. Kohda, K., Baba, K., and Kawazoe, Y. (1986) Synthesis of 7-Aminoguanosine and its conversion to 8-substituted derivatives. Chem. Pharm. Bull. 34, 2298–2301.
31. Gassmann, P. G., and Cryberg, R. L. (1969) The discrete existence of singlet and triplet nitrenium ions. J. Am. Chem. Soc. 91, 5176–5177.
32. Lee, S. T., and Morokuma, K. (1971) Ab initio molecular orbital studies on the structure of the nitrenium ion and its implications. J. Am. Chem. Soc. 93, 6863–6866.
33. Gassman, P. G. (1970) Nitrenium ions. Acc. Chem. Res. 3, 26–33.
34. Kohl, C., Schiller, C. D., Gescher, A., Farmer, P. B., and Bailey, E. (1992) Acetoxime is metabolized by human and rodent hepatic cytochrome P450 enzymes to the genotoxicant and carcinogen propane 2-nitronate. Carcinogenesis 13, 1091–1094.
35. Haas-Jobelius, M., Ziegler-Skylakakis, K., and Andrae, U. (1991) Nitroreduction is not involved in the genotoxicity of 2-nitropropane in cultured mammalian cells. Mutagenesis 6, 87–91.
36. Floyd, R. A., Watson, J. J., Wong, P. K., Altmiller, D. H., and Rickard, R. C. (1986) Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanism of formation. Free Radical Res. Commun. 1, 163–172.