Amination of tyrosine in liver cytosol protein of male F344 rats treated with 2-nitropropane, 2-nitrobutane, 3-nitropentane, or acetoxime

Chemical Research in Toxicology

Volumn 10, Issue 12, 1997, Pages 1420-1426

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

^a AMERICAN HEALTH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROPROPANE; 8 AMINOGUANOSINE; BUTANE; CARCINOGEN; CELL PROTEIN; NITROALKANE; OXIME; PENTANE; TYROSINE;

AMINATION; ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; LIVER CARCINOGENESIS; LIVER CYTOSOL; MALE; NONHUMAN; PROTEIN MODIFICATION; RAT;

ALKANES; AMINATION; ANIMALS; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOSOL; LIVER; MALE; NITROPARAFFINS; OXIMES; PROPANE; RATS; RATS, SPRAGUE-DAWLEY; TYROSINE;

ANIMALIA;

EID: 0031459260     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970137b     Document Type: Article

References (45)

1. 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.
2. WHO. (1992) Environmental Health Criteria 138: 2-Nitropropane, World Health Organization, Geneva, Switzerland.
3. Løfroth, G., Nilsson, L., and Anderson, J. R. (1986) Structure-activity relationship of nitroalkane-induced mutagenicity in the Ames Salmonella assay. Genetic Toxicology of Environmental Chemicals. Part B: Genetic Effects and Applied Mutagenesis, pp 149-155, Alan Liss, Inc., New York.
4. 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 nitro compounds in the Ames Salmonella assay. Mutat. Res. 261, 197-207.
5. 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.
6. Davies, J. E., Mynett, K., Gescher, A., and Chipman, J. K. (1993) DNA modifications and repair by 2-nitropropane is extensive in hepatocytes of rats compared to those of human and mice. Mutat. Res. 287, 157-164.
7. Fiala, E. S., Sodum, R. S., Hussain, N. S., Rivenson, A., and Dolan, L. (1995) Secondary nitroalkanes: Induction of DNA repair in rat hepatocytes, activation by aryl sulfotransferase and hepatocarcinogenecity of 2-nitrobutane and 3-nitropentane in male F344 rats. Toxicology 99, 89-97.
8. 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.
9. 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.
10. Fiala, E. S., Conaway, C. C., and 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.
11. Sodum, R. S., Nie, G., and Fiala, E. S. (1993) 8-Arninoguanine: A base modification produced in rat liver nucleic acids by the hepatocarcinogen 2-nitropropane. Chem. Res. Toxicol. 6, 269-276.
12. Sodum, R. S., Sohn, O. S., Nie, G., and Fiala, E. S. (1994) Activation of the liver carcinogen 2-nitropropane by aryl sulfotransferase. Chem. Res. Toxicol. 7, 344-351.
13. 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 carcinogen- esis by Af-arylhydroxylamines. Chem. Pharm, Bull. 20, 2073-2074.
14. Nielsen, A. T. (1981) Nitronic acids and esters. In The Chemistry of the Nitro and Nitroso Groups, Part I (Feuer, H., Ed.) pp 349-386, Robert E. Krieger Publishing Co., Huntington, NY.
15. 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,
16. Hussain, N. B., Conaway, C. C., Guo, N., Asaad, W., 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.
17. Kohl, C., Schiller, C. D., Gescher, A., Farmer, P., 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.
18. Holmes, R. E., and Robins, R. K. (1965) Purine nucleosides. IX. The synthesis of 9-β-D-ribofuranosyl uric acid and other related 8-substitued purine ribonucleosides. J. Am. Chem. Soc, 87, 1772-1776.
19. Broom, A. D., and Robins, R. K. (1969) Purine nucleosides. XXIII. Direct amination of purine nucleosides. J. Org. Chem. 34, 1025-1029.
20. Smith, P. A. (1948) Ketoxime-O-sulfonic acids. J. Am. Chem. Soc. 70, 323-326.
21. Ohshima, H., Friesen, M., Brouet, I., and Bartsch, H. (1990) Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food Chem. Toxicol. 647-652.
22. Kooy, N. W., Royall, J. A., Ye, Y. Z., Kelly, D. R., and Beckman, J. S. (1995) Evidence for in vivo peroxynitrite production in human acute lung injury. Am. J. Respir. Crit. Care Med. 151, 1250-1254.
23. Beckmann, J. S., Ye, Y. Z., Anderson, P. G., Chen, J., Accavitti, M. A., Tarpey, M. M., and White, C. R. (1994) Extensive nitration of protein tyrosine in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler 375, 81-88.
24. Sanford, J. K., Blair, F. T., Arroya, J., and Sherk, K. W. (1945) The reaction of hydroxylamine-O-sulfonic acid with ketones. J. Am. Chem. Soc. 67, 1941-1943.
25. Prubek, D., Rundtrenm, M., Larsson, R., Albano, E., Ross, D., Nelson, S. D., and Moldeus, P. (1986) Quinone imines as biological reactive intermediates. In Biological Reactive Intermediates III. Mechanisms of Action in Animal Models and Human Diseases (Kocsis, J., Jollow, D. J., Witmer, C. M., Nelson, J. O., and Snyder, R., Eds.) pp 638-640, Plenum Press, New York.
26. Eckert, K-G., and Eyer, P. (1983) Differences in the reactions of isomeric ortho- and para-aminophenols with hemoglobin. Biochem. Pharmacol. 32, 1019-1027.
27. Berger, J. M., gamblin, S. J., Harrison, S. C., and Wang, J. C. (1996) Structure and mechanism of DNA topoisomerase II. Nature 379, 225-232.
28. Bollinger, J. M., Jr., Edmondson, D. E., Huynh, B. H., Filley, J., Norton, J. R., and Stubbe, J. (1991) Mechanism of assembly of the tyrosyl radical-dinuclear iron cluster cofactor of ribonucleotide reductase. Science 253, 292-298.
29. Chern, J.-W., Lee, H.-Y., and Chen, C.-S. (1993) Nucleosides, 5. Synthesis of guanine and formycin B derivatives as potential inhibitors of purine nucleoside phosphorylase. J. Med. Chem. 36, 1024-1031.
30. Ealick, S. E., Rule, S. A., Carter, D. C., Greenhough, T. J., Babu, Y. S., Cook, W. J., Habash, J., Helliwell, J. R., Stoeckler, J. D., Parks, R. E., Jr., Chen, S.-F., and Bugg, C. E. (1990) Three-dimensional structure of human erythrocytic purine nucleoside phosphorylase at 3.2 Å resolution. J. Biol. Chem. 265, 1812-1820.
31. Bottaro, D. P., Rubin, J. S., Faletto, D. L., Chan, A. M., Kimecik, T. E., Vande Woude, G. F., and Aaronson, S. (1991) Identification of the hepatocyte growth factor receptor as the c-met protooncogene product. Science 251, 802-804.
32. Martin, B. L., Wu, D., Jakes, S., and Graves, D. J. (1990) Chemical influences on the specificity of tyrosine phosphorylation. J. Biol. Chem. 265, 7108-7111.
33. Gow, A. J., Duran, D., Malcolm, S., and Ischiropoulos, H. (1996) Effects of peroxynitrite-induced protein modifications on tyrosine phosphorylation and degradation. FEBS Lett. 385, 63-66.
34. Sokolovsky, M., Riordan, J. F., and Vallee, B. L. (1967) Conversion of 3-nitrotyrosine to 3-aminotyrosine in peptides and proteins. Biochem. Biophys. Res. Commun. 27, 20-25.
35. Seagle, R. L., and Cowgill, R. W. (1976) Fluorescence and the structure of proteins. XXII. Fluorescence of aminotyrosyl residues formed in ribonuclease A. Biochim. Biophys. Acta 439, 470-478.
36. Kochhar, S., and Dua, R. D. (1985) Chemical modification of liquifying a-amylase: Role of tyrosine residues at its active center. Arch. Biochem. Biophys. 240, 757-767.
37. Cymes, G. D., and Wolfenstein-Todel, C. (1996) Identification of a tyrosine residue in ovine placental lactogen as essential for its binding to receptors. Biochim. Biophys. Acta 1294, 31-36.
38. Hecht, S. S., Carmella, S. G., and Murphy, S. E. (1994) Tobaccospecific nitrosamine-hemoglobin adducts. Methods Enzymol. 231, 657-667.
39. Newmann, H. G., Birner, G., Kowallik, P., Schultze, D., and Zwirner-Baier, I. (1993) Hemoglobin adducts of N-substituted aryl compounds in exposure control and risk assesment. Environ. Health Persp. 99, 65-69.
40. Skipper, P. L., and Stillwell, W. G. (1994) Aromatic aminehemoglobin adducts. Methods Enzymol. 231, 643-649.
41. Day, B. W., and Singh, K. (1994) Analysis of hemoglobin adducts by fluorescence spectroscopy. Methods Enzymol. 231, 674-684.
42. Tornqvist, M. (1994) Epoxide adducts to N-terminal valine of hemoglobin. Methods Enzymol. 231, 650-656.
43. Bergmark, E. (1997) Hemoglobin adducts of acrylamide and acrylonitrile in laboratory workers, smokers, and nonsmokers. Chem. Res. Toxicol. 10, 78-84.
44. Taghizadeh, K., and Skipper, P. L. (1994) Benzo[a]pyrene diol epoxide and related polynuclear aromatic hydrocarbon adducts of hemoglobin. Methods Enzymol. 231, 668-673.
45. Debaun, J. R., Miller, E. C., and Miller, J. A. (1970) N-Hydroxy-2-acetylaminofluorene sulfotransferase: Its probable role in carcinogenesis and in protein-(methion-S-yl) binding in rat liver. Cancer Res. 30, 577-595.