DNA damage by nitric oxide

Chemical Research in Toxicology

Volumn 9, Issue 5, 1996, Pages 821-827

  Tamir, Snait ^a   Burney, Samar ^a   Tannenbaum, Steven R ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITRIC OXIDE;

ANIMAL CELL; ARTICLE; AUTOOXIDATION; CHO CELL; CONTROLLED STUDY; DNA DAMAGE; DNA REPAIR; GENOTOXICITY; HUMAN; HUMAN CELL; INFECTION; MUTAGENICITY; NONHUMAN; OXIDATIVE STRESS; PHAGOCYTOSIS; TARGET CELL; TISSUE INJURY;

BACTERIA; CELLS, CULTURED; DNA DAMAGE; DNA REPAIR; HUMANS; NITRIC OXIDE; SACCHAROMYCES CEREVISIAE;

EID: 0029682435     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9600311     Document Type: Article

References (61)

1. Tannenbaum S. R., Tamir, S., and Walker, T. (1994) DNA damage and cytotoxicity by nitric oxide. In Nitrosamines and related N-nitroso compounds chemistry and biochemistry (Loeppky, R. N., and Michejda, C. J., Eds.) ACS Symposium Series 553, pp 120-135, American Chemical Society, Washington, DC.
2. Ischiropoulos, H., Zhu, L., and Beckman, J. S. (1992) Peroxynitrite formation from macrophage-derived nitric oxide. Arch. Biochem. Biophys. 298, 446-451.
3. Koppenol, W. H., Pryor, W. A., Moreno, J. J., Ischiropoulos, H., and Beckman, J. S. (1992) Peroxynitrite, a cloaked oxidant formed by nitric oxide and Superoxide. Chem. Res. Toxicol. 6, 834-842.
4. Pryor, W. A., and Squadrito, G. L. (1995) The chemistry of peroxynitrite: a product from the reaction of nitric oxide with Superoxide. Am. J. Physiol. 268 (Lung Cell. Mol. Physiol. 12), L699-L722.
5. Lepoivre, M., Flaman, J.-M., Bobe, P., Lemaire, G., and Henry, Y. (1994) Quenching of the tyrosyl free radical of ribonucleotide reductase by nitric oxide. J. Biol. Chem. 269, 21891-21897.
6. Weiss, G., Goossen, B., Doppier, W., Fuchs, D., Pantopoulos, K., Werner-Femayer, G., Wachter, H., and Hentze, M. W. (1993) Translational regulation via iron-responsive elements by the nitric oxide/NO-synthase pathway. EMBO J. 12, 3651-3657.
7. Hartman, P. E., Ames, B. N., Roth, J. R., Barnes, W. M., Levin, D. E. (1986) Target sequences for mutagenesis in Salmonella histidine-requiring mutants. Environ. Mulagen. 8, 631-641.
8. Weber, C. A., Saazar, P. A., Stewart, S. A., and Thompson, L. H. (1987) Molecular cloning and biological characterization of a human gene, ERCC2, that corrects the nucleotide excision repair defect in CHO UV5 cells. Mol. Cell. Biol. 8, 1137-1146.
9. Thompson, L. H., Brookman, K. W., Jones, N. J., Allen, S. A., and Carrano, A. V. (1990) Molecular cloning of human XRCC1 gene, which corrects defective DNA strand break repair and sister chomatid exchange. Mol. Cell. Biol. 10, 6160-6171.
10. Thompson, L. H., Busch, D. B., Brookman, K., Mooney, C. L., and Glaser, D. A. (1981) Genetic diversity of UV-sensitive DNA repair mutants of Chinese hamster ovary cells. Proc. Natl. Acad. Sci. U.S.A. 78, 3734-3737.
11. deRojas-Walker, T., Tamir, S., Ji, H., Wishnok, J. S., Tannenbaum, S. R. (1995) Nitric oxide induces oxidative damage in addition to deamination in macrophage DNA. Chem. Res. Toxicol. 8, 473-477.
12. Strathdee, C. A., Gavish, H., Shannon, W. R., and Buchwald, M. (1992) Cloning of cDNA for Fanconi's anaemia by functional complementation. Nature 356, 763-765.
13. Nicotera, T. M. (1991) Molecular and biochemical aspects of Bloom's syndrome. Cancer Genet. Cytogenet. 53, 1-13.
14. Tamir, S., Lewis, R. S., Walker, T., Deen, W. M., Wishnok, J. S., and Tannenbaum, S. R. (1993) The influence of delivery rate on the chemistry and biological effects of nitric oxide. Chem. Res. Toxicol. 6, 895-899.
15. 15N]-nitrate in biological fluids. Anal. Biochem. 126, 131-138.
16. Tamir, S., Wishnok, J. S., and Tannenbaum S. R. (1996) DNA damage and genotoxicity by nitric oxide. In Nitric Oxide (Packer, L., Ed.) Methods in Enzymology Series, Vol. 269, pp 230-243, Academic Press, New York.
17. Maron, D. M., and Ames, B. N. (1983) Revised methods for the salmonella mutagenicity test. Mutat. Res. 113, 173-215.
18. Impellizzeri, K. J., Anderson, B., and Burgers, P. M. (1991) The spectrum of spontaneous mutations in a Saccharomyces cereuisiae uracil-DNA-glycosylase mutant limits the function of this enzyme to cytosine deamination repair. J. Bacteriol. 173, 6807-6810.
19. King, P. A., Anderson, V. E., Edwards, J. O., Gustafson, G., Plumb, R. C., and Suggs, J. W. (1992) A stable solid that generates hydroxyl radical upon dissolution in aqueous solutions: reaction with proteins and nucleic acid. J. Am. Chem. Soc. 114, 5430-5432.
20. Nguyen, T., Brunson, D., Crespi, C. L., Penman, B. W., Wishnok, J. S., and Tannenbaum, S. R. (1992) DNA damage and mutation in human cells exposed to nitric oxide in vitro. Proc. Natl. Acad. Sci. U.S.A. 89, 3030-3034.
21. Eustice, D. C., Feldman, P. A., Coldberg-Poley, A. M., Buckery, R. M., and Neubauer, R. H. (1991) A sensitive method for the detection of β-galactosidase in transfected mammalian cells. Biotechniques 11, 739-742.
22. Salgo, M. G., Stone, K., Squadrito, G. L., Battista, J. R., and Pryor, W. A. (1995) Peroxynitrite causes DNA nicks in plasmid pBR322. Biochem. Biophys. Res. Commun. 210, 1025-1030.
23. Routledge, M. N., Wink, D. A., Keefer, L. K., and Dipple, A. (1994) DNA sequence changes induced by two nitric oxide donor drugs in the supF assay. Chem. Res. Toxicol. 7, 628-632.
24. Schmutte, C., Rideout, W. M., III, Shen, J.-C., and Jones, P. A. (1994) Mutagenicity of nitric oxide is not caused by deamination of cytosine or 5-methylcytosine in double-stranded DNA. Carcinogenesis 15, 2899-2903.
25. Saparbaev, M., and Laval, J. (1994) Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat, and human alkylpurine DNA glycosylases. Proc. Natl. Acad. Sci. U.S.A. 91, 5873-5877.
26. Shapiro, R., Dubelman, S., Feinberg, A. M., Crain, P. F., and McCloskey, J. A. (1977) Isolation and identification of cross linked nucleosides from nitrous acid treated deoxyribonucleic acid. J. Am. Chem. Soc. 99, 302-303.
27. Drysdale, B. E., Agarwal, S., and Shin, H. S. (1988) Macrophage-mediated tumoricidal activity: mechanisms of activation and cytotoxicity. Prog. Allergy 40, 111-161.
28. Nathan, C. (1992) Nitric oxide as a secretory product of mammalian cells. FASEB J. 6, 3051-3064.
29. Wink, D. A., Kasprzak, K. S., Maragos, C. M., Elespru, R. K., Misra, M., Dunams, T. M., Cebula, T. A., Koch, W. H., Andrews, A. W., Aleen, J. S., and Keefer, L. K. (1991) DNA deaminating ability and genotoxicity of nitric oxide and its progenitors. Science 254, 1001-1003.
30. Greenblatt, M. S., Bennett, W. P., Hollstein, M., and Harris, C. C. (1994) Mutations in the p53 tumor suppressor gene: clues to cancer etiology and molecular pathogenesis. Cancer Res. 54, 4855-4878.
31. Hill-Perkins, M., Jones, M. D., and Karran, P. (1986) Site-specific mutagenesis in vivo by single methylated or deaminated purine bases. Mutat. Res. 162, 153-163.
32. Kamiya, H., Shimizu, M., Suzuki, M., Inoue, H., and Ohtsuka, E. (1992) Mutation induced by deoxyxanthosine in codon 12 of a synthetic c-Ha-ras gene. Nucleosides Nucleotides 11, 247-260.
33. Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., and Freeman, B. A. (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and Superoxide. Proc. Natl. Acad. Sci. U.S.A. 87, 1620-1624.
34. Nunoshiba, T., deRojas-Walker, T., Wishnok, J. S., Tannenbaum, S. R., and Demple, B. (1993) Activation by nitric oxide of an oxidative-stress response that defends Escherichia coli against activated macrophages. Proc. Natl. Acad. Sci. U.S.A. 90, 9993-9997.
35. Nunoshiba, T., DeRojas-Walker, T., Tannenbaum, S. R., and Demple, B. (1995) Roles of nitric oxide in inducible resistance of Escherichia coli to activated murine macrophages. Infect. Immun. 63, 794-798.
36. Radi, R., Beckman, J. S., Bush, K. M., and Freeman, B. A. (1991) Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of Superoxide and nitric oxide. Arch. Biochem. Biophys. 288, 481-487.
37. Pryor, W. A., Jin, X., and Squadrito, G. L. (1994) One- and two-electron oxidations of methionine by peroxynitrite. Proc. Natl. Acad. Sci U.S.A. 91, 11173-11177.
38. Darley-Usmar, V. M., Hogg, N., O'Leary, V. J., Wilson, M. T., and Moncada, S. (1992) The simultaneous generation of Superoxide and nitric oxide can initiate lipid peroxidation in human low density lipoprotein. Free Radical Res. Commun. 17, 9-20.
39. Graham, A., Hogg, N., Kalyanaraman, B., O'Leary, V., Darley-Usmar, V., and Moncada, S. (1993) Peroxynitrite modification of low-density lipoprotein leads to recognition by the macrophage scavenger receptor. FEBS Lett. 330, 181-185.
40. Yermilov, V., Rubio, J., and Ohshima, H. (1995) Formation of 8-nitroguanine in DNA treated with peroxynitrite in vitro and its rapid removal from DNA by depurination. FEBS Lett. 376, 207-210.
41. Douki, T., Cadet, J., and Ames, B. N. (1996) An adduct between peroxynitrite and 2′-deoxyguanosine: 4,5-dihydro-5-hydroxy-4-(nitrosooxy)-2′-deoxyguanosine. Chem. Res. Toxicol. 9, 3-7.
42. Ramezanian, M. S., Padmaja, S., and Koppenol, W. H. (1996) Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chem. Res. Toxicol. 9, 232-240.
43. Juedes, M. J., and Wogan, G. N. (1996) Peroxynitrite-induced mutation spectra of pSP189 following replication in bacteria and in human cells. Mutat. Res. 349, 51-61.
44. Chong, Y. C., Heppner, G. H., Paul, L. A., and Fulton, A. M. (1989) Macrophage-mediated induction of DNA strand breaks in target tumor cells. Cancer Res. 49, 6652-6657.
45. Eastman, A., and Barry, M. A. (1992) The origins of DNA breaks: A consequence of DNA damage or apoptosis? Cancer Invest. 10, 229-240.
46. Friedberg, E. C. (1985) DNA Repair, W. H. Freeman and Co., New York.
47. Ross, W. (1985) DNA topoisomerases as targets for cancer therabasicy. Biochem. Pharmacol. 34, 4191-4195.
48. Wink, D. A., and Laval, J. (1994) The Fpg protein, a DNA repair enzyme, is inhibited by the biomediator nitric oxide in vitro and in vivo. Carcinogenesis 15, 2125-2129.
49. 6-methylguanine-DNA-methyltransferase. Carcinogenesis 15, 443-447.
50. Geidushek, E. P. (1961) Reversible DNA. Proc. Natl. Acad. Sci. U.S.A. 47, 950-955.
51. Schuster, H., and Wilhelm, R. C. (1963) Reaction differences between tobacco mosaic virus and its free ribonucleic acid with nitrous acid. Biochim. Biophys. Acta 68, 554-560.
52. 2. J. Biol. Chem. 246, 5914-5918.
53. Kirchner, J. J., and Hopkins, P. B. (1991) Nitrous acid cross-links duplex DNA fragments though deoxyguanosine residues at the sequence 5′-CG. J. Am. Chem. Soc. 113, 4681-4682.
54. Kirchner, J. J., Sigurdsson, S. T., and Hopkins, P. B. (1992) Interstrand cross-linking of duplex DNA by nitrous acid: covalent structure of the dG-to-dG cross-link at the sequence 5′-CG. J. Am. Chem. Soc. 114, 4021-4027.
55. Dizdaroglu, M., and Gajewski, E. (1989) Structure and mechanism of hydroxyl radical-induced formation of a DNA-protein cross-link involving thymine and lysine in nucleohistone. Cancer Res. 49, 3463-3467.
56. Nackerdien, Z., Rao, M. A., Cacciuttolo, E., Gajewski, E., and Dizdaroglu, M. (1991) Chemical nature of DNA protein cross-links produced in mammalian chomatin by hydrogen peroxide in the presence of iron or copper ions. Biochemistry 30, 4873-4879.
57. Potti, N. D., and Bello, J. (1971) Cross-linking of nucleohistone by nitrous acid. Mutat. Res. 12, 113-119.
58. Hartman, Z., Henrikson, E. N., Hartman, P. E., and Cebula, T. A. (1994) Molecular models that may account for nitrous acid mutagenesis in organisms containing double-stranded DNA. Environ. Mol. Mutagen. 25, 168-175.
59. Frankel, A. D., Duncan, B. K., and Hartman, P. E. (1980) Nitrous acid damage to duplex deoxyribonucleic acid: distinction between deamination of cytosine residues and a novel mutational lesion. J. Bacteriol. 142, 335-338.
60. Grishko, V. I., Druzhyana, N., Patton, N. J., LeDoux, S. P., and Wilson, G. L. (1996) Mitochondrial DNA is damaged by nitric oxide. Proceedings of the AACR, Abstract #852, Vol. 37, p 123, April 20-24, Washington, DC.
61. Lewis, R. S., Tamir, S., Tannenbaum, S. R., and Deen, W. M. (1995) Kinetic analysis of the fate of nitric oxide synthesized by macrophages in vitro. J. Biol. Chem. 270, 29350-29355.