Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 27, 1997 - Issue 8
27
Views
5
CrossRef citations to date
0
Altmetric
Research Article

Denitrification of the genotoxicant 2-nitropropane : relationship to its mechanism of toxicity

&
Pages 843-852 | Published online: 22 Sep 2008

References

  • 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. Carcinogen esis, 9, 811–815.
  • BOILS, W., MICHEL, C., DALKE, C., STETTMAIER, K., SARAN, M. and ANDRAE, U., 1993, Radical intermediates during the oxidation of nitropropanes. The formation of NO2 from 2-nitropropane, its reactivity with nucleosides, and implications for the genotoxicity of 2-nitropropane. Chemical Research in Toxicology, 6, 302–309.
  • CAIN, K. and SKILLETER, D. N., 1987, Preparation and use of mitochondria in toxicological research. In Biochemical Toxicology edited by K. Snell and B. Mullock (Oxford: IRL), pp. 217–252.
  • CHIPMAN, J. K., DAVIES, J. E. and PATERSON, P., 1987, Mechanisms of butylated hydroxy-toluene-mediated modulation of 2-acetylaminofluorene mutagenicity in rat and human hepatocyte/ Salmonella assays. Mutation Research, 187, 105–112.
  • CONAWAY, C. C., HUSSAIN, N. S., WAY, B. M. and FIALA, E. S., 1991, Evaluation of secondary nitroalkanes, nitrocarbinols, and other aliphatic nitro compounds in the Ames Salmonella assay. Mutation Research, 261, 197–207.
  • DALKE, C. and ANDRAE, U., 1992, Propane 2-nitronate is more rapidly denitrified and is more genotoxic than 2-nitropropane in cultured rat hepatoma cells. Toxicology Letters, 61, 149–157.
  • DAVIES, J. E., MYNETT, K., GESCHER, A. and CHIPMAN, J. K., 1993, DNA modification and repair by 2-nitropropane is extensive in hepatocytes of rats compared to those of humans and mice. Mutation Research, 287, 157-1 64 .
  • DAYAL, R., GESCHER, A., HARPUR, E. S., PRATT, I. and CHIPMAN, J. K., 1987, Comparison of the hepatotoxicity in mice and the mutagenicity of three nitroalkanes. Fundamentals in Applied Toxicology, 13, 341–348.
  • DAYAL, R., GOODWIN, B., LINHART, I., MYNETT, K. and GESCHER, A., 1991, Oxidative denitrification of 2-nitropropane and propane 2-nitronate by mouse liver microsomes : lack of correlation with hepatocytotoxic potential. Chemico-Biological Interactions, 79, 103–114.
  • DENK, B., BAUMANN, M. and FILSER, J. G., 1989, Pharmacokinetics and hepatotoxicity of 2-nitropropane in rats. Archives in Toxicology, Suppl. 13, 330–332.
  • DEQUIDT, J., VASSEUR, P. and POTENCIER, J., 1972, Etude toxicologique experimentale de quelques Nitroparaffines. 1°-Etude du 2-nitropropane. Bulletin Societe' Pharmaceutique de Lille, 2, 83–89.
  • DE RYCKER, J. and HALLIWELL, B., 1978, Oxidation of 2-nitropropane by horseradish peroxidase. Involvement of hydrogen peroxide and of superoxide in the reaction mechanism. Biochemical Journal, 175, 601–606.
  • FEELISCH, M. and NOACK, E. A., 1987, Correlation between nitric oxide formation during degradation of organic nitrates and activation of guanylate cyclase. European Journal of Pharmacology, 139, 19–30.
  • FIALA, E. S., CONAWAY, C. C., BILES, W. T. and JOHNSON, B. T., 1987a, Enhanced mutagenicity of 2-nitropropane nitronate with respect to 2-nitropropane—possible involvement of free radical species. Mutation Research, 179, 15–22.
  • FIALA, E. S., CZERNIAK, R., CASTONGUAY, A., CONAWAY, C. C. and RIVENSON, A., 1987b, Assay of 1-nitropropane, 2-nitropropane, 1-azoxypropane and 2-azoxypropane for carcinogenicity by gavage in Sprague—Dawley rats. Carcinogenesis, 8, 1947–1949.
  • HABIG, W. H., PABST, M. J. and JACOBY, W. B., 1974, Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. Journal of Biological Chemistry, 249, 7130–7139.
  • HITE, M. and SICEGGS, H., 1979, Mutagenic evaluation of nitroparaffins in Salmonella typhimurium/mammalian microsome test and micronucleus test. Environmental Mutagenisis, 1, 383–389.
  • HOFFMANN, D. and RATHKAMP, G., 1968, Chemical studies on tobacco smoke. III. Primary and secondary nitroalkanes. Beiträge zur Tabakforschung, 4, 124–134.
  • KOHL, C. and GESCHER, A., 1996, Catalysis of nitro-aci tautomerism of the genotoxicant 2-nitropropane by cytosol from rodent and human liver. Chemko-Biological Interactions, 99, 219–226.
  • KOHL, C., MORGAN, P. and GESCHER, A., 1995, Metabolism of the genotoxicant 2-nitropropane to a nitric oxide species. Chemico-Biological Interactions, 97, 175–184.
  • KOHL, C., MYNETT, K., DAVIES, J. E., GESCHER, A. and CHIPMAN, J. K., 1994, Propane 2-nitronate is the major genotoxic form of 2-nitropropane. Mutation Research, 321, 65–72.
  • KoNros, H. A. and WEI, E. P., 1993, Hydroxyl radical-dependent inactivation of guanylate cyclase in cerebral arterioles by methylene blue and by LY83583. Stroke, 24, 427–434.
  • KRESGE, A. J., 1974, The nitroalkane anomaly. Canadian Journal of Chemistry, 52, 1897–1903.
  • Kuo, C. F. and FRIDOVICH, I., 1986, Free-radical chain reaction of 2-nitropropane initiated and propagated by superoxide. Biochemical Journal, 237, 505–510.
  • LAKE, G. B., 1987, Preparation and characterisation of microsomal fractions for studies on xenobiotic metabolism. In Biochemical Toxicology, edited by K. Snell and B. Mullock (Oxford: IRL), pp. 183–215.
  • LEATITWOOD, P. D. and PLUMMER, D. T., 1969, Enzymes in rat urine. 1. A metabolism cage for the complete separation of urine and faeces Enzymologia, 37, 240–250.
  • LEE, Y. S. and WURSTER, R. D., 1995, Methylene blue induces cytotoxicity in human brain tumor cells. Cancer Letters, 88, 141–145.
  • LEWIS, T. R., ULRICH, C. E. and BUSHY, W. M., 1979, Subchronic inhalation toxicity of nitromethane and 2-nitropropane. Journal of Environmental Pathology and Toxicology, 2, 233–249.
  • LINHART, I., GESCHER, A. and GOODWIN, B., 1991, Investigation of the chemical basis of nitroalkane toxicity: tautomerism and decomposition of propane 1-nitronate and propane 2-nitronate under physiological conditions. Chemko-Biological Interactions, 80, 187–201.
  • LOFROTH, G., NILSSON, L. and ANDERSEN J. R., 1986, Structure—activity relationship of nitroalkane-induced mutagenicity in the Ames Salmonella assay. Progress in Clinical Biological Research, 209B, 149–155.
  • LOWRY, 0. H., ROSEBOROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the folin-phenol reagent. Journal Biological Chemistry, 193, 265–275.
  • MARCZIN, N., RYAN, U. S. and CATRAVAS, J. D., 1992, Methylene blue inhibits nitrovasodilator- and endothelium-derived relaxing factor-induced cyclic GMP accumulation in cultured pulmonary arterial smooth muscle cells via generation of superoxide anion. Journal of Pharmacology and Experimental Therapeutics, 263, 170–179.
  • MARKER, E. K. and KULKARNI, A. P., 1986, Cytochrome P-450-mediated denitrification of 2-nitropropane in mouse liver microsomes. Journal of Biochemistry and Toxicology, 1, 71-83. MOLDEUS, P., HOGBERG J. and ORRENIUS S., 1978, Isolation and use of liver cells. Methods in Enzymology, 52, 60–71.
  • PETRELLI, G., SIEPI, G., MILIGI, L. and VINEIS, P., 1993, Solvents in pesticides. Scandinavian Journal of Work and Environmental Health, 19, 63–65.
  • PORTER, D. J. T. and BRIGHT, H. J., 1983, The mechanism of oxidation of nitroalkanes by horseradish oxidase. Journal of Biological Chemistry, 258, 9913–9924.
  • RICKWOO D., 1987, Centrifugation, 2nd edn (Oxford: IRL), p. 314.
  • SCHROR, K., FORSTER, S. and WODITSCH, I., 1991, On-line measurement of nitric oxide release from organic nitrates in the intact coronary circulation. Naunyn-Schmiedeberg's Archives of Pharma-cology, 344, 240–246.
  • SEGLEN, P. 0., 1976, Preparation of isolated rat liver cells. Methods in Cell Biology, 13, 29–83.
  • SHAW, A. J., GESCHER, A. and MRAZ, J., 1988, Cytotoxicity and metabolism of the hepatotoxin N-methylformamide and related formamides in mouse hepatocytes. Toxicology and Applied Pharmacology, 95, 162–170.
  • SPECK, W. T., MEYER, L. W., ZEIGER, E. and ROSENKRANZ, H. S., 1982, Mutagenicity and DNA-modifying activity of 2-nitropropane. Mutation Research, 104, 49–54.
  • TREON J. F. and DUTRA, F. R., 1952, Physiological response of experimental animals to the vapor of 2-nitropropane. Archives of Industrial Hygiene and Occupational Medicine, 5, 52–61.
  • ULLRICH V., HERMANN, G. and WEBER, P., 1978, Nitrite formation from 2-nitropropane by microsomal monoxygenases. Biochemical Pharmacology, 27, 2301–2304.
  • VINCE, R. and WADD, W. B., 1969, Glyoxalase inhibitors as potential anticancer drugs. Biochemical and Biophysical Research Communications, 35, 593–598.
  • WHO, 1992, Environmental Health Criteria 138: 2-Nitropropane (Geneva: World Health Organization).
  • WOLIN, M. S., CHERRY, P. D., RODENBURG, J. M., MESSINA, E. J. and RALEY, G., 1990, Methylene blue inhibits vasodilation of skeletal muscle arterioles to acetylcholine and nitric oxide via the extracellular generation of superoxide anion. Journal of Pharmacology and Experimental Thera-peutics, 254, 872–875.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.