Toxicity of peroxynitrite and related reactive nitrogen species toward Escherichia coli

Chemical Research in Toxicology

Volumn 10, Issue 7, 1997, Pages 802-810

  Hurst, James K ^a   Lymar, Sergei V ^a,b  

^a WASHINGTON STATE UNIVERSITY   (United States)

^b BROOKHAVEN NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; HYDROGEN PEROXIDE; NITROGEN; PEROXYNITRITE;

ARTICLE; BACTERICIDAL ACTIVITY; ESCHERICHIA COLI; LD 50; NONHUMAN; REACTION ANALYSIS;

ESCHERICHIA COLI; FREE RADICALS; HYDROGEN PEROXIDE; KINETICS; LETHAL DOSE 50; NITRATES; NITROSO COMPOUNDS; OXIDANTS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 0030747834     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970008v     Document Type: Article

References (70)

1. Koppenol, W. H., Moreno, J. J., Pryor, W. A., Ischiropoulos, H., and Beckman, J. S. (1992) Peroxynitrite, a cloaked oxidant formed by nitric oxidant and superoxide. Chem. Res. Toxicol. 5, 834-842.
2. -. Free Radical Res. Commun. 18, 195-199.
3. Radi, R., Beckman, J. S., Bush, K. M., and Freeman, B. A. (1991) Peroxynitrite oxidation of sulfhydryls. J. Biol. Chem. 266, 4244-4250.
4. Radi, R., Beckman, J. S., Bush, K. M., and Freeman, B. A. (1991) Peroxynitrite-induced membrane lipid peroxidation. Arch. Biochem. Biophys. 288, 481-487.
5. Moreno, J. J., and Pryor, W. A. (1992) Inactivation of α1-proteinase inhibitor by peroxynitrite. Chem. Res. Toxicol. 5, 425-431.
6. Beckman, J. S., Ischiropoulos, H., Zhu, L., van der Woerd, M., Smith, C., Chen, J., Harrison, J., Martin, J. C., and Tsai, M. (1992) Kinetics of superoxide dismutase- and iron-catalyzed nitration of phenolics by peroxynitrite. Arch. Biochem. Biophys. 298, 438-445.
7. Bauer, M. L., Beckman, J. S., Bridges, R. J., Fuller, C. M., and Matalon, S. (1992) Peroxynitrite inhibits sodium uptake in rat colonic membrane vesicles. Biochim. Biophys. Acta 1104, 87-94.
8. Hausladen, A., and Fridovich, I. (1994) Superoxide and peroxynitrite inactivate aconitases, but nitric oxide does not. J. Biol. Chem. 269, 29405-29408.
9. Castro, L., Rodriguez, M., and Radi, R. (1994) Aconitase is readily inactivated by peroxynitrite but not by its precursor nitric oxide. J. Biol. Chem. 269, 29409-29415.
10. Ischiropoulos, H., and Al-Mehdi, A. B. (1995) Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 364, 279-282.
11. Berlett, B. S., Friguet, M. B., Chock, P. B., and Stadtman, E. R. (1996) Peroxynitrite-mediated nitration of tyrosine residues in Escherichia coli glutamine synthetase mimics adenylylation: relevance to signal transduction. Proc. Natl. Acad. Sci. U.S.A. 93, 1776-1780.
12. Beckman, J. S., and Crow, J. P. (1993) Pathological implications of nitric oxide, superoxide and peroxynitrite formation. Biochem. Soc. Trans. 21, 330-334.
13. Graham, A., 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.
14. Beckman, J. S. (1991) The double-edged role of nitric oxide in brain function and superoxide-mediated injury. J. Develop. Physiol. 15, 53-59.
15. Szabo, C., Salzman, A. L., and Ischiropoulos, H. (1995) Peroxynitrite-mediated oxidation of dihydrorhodamine 123 occurs in early stages of endotoxic and hemorrhagic shock and ischemia-reperfusion injury. FEBS Lett. 372, 229-232.
16. Denis, M. (1994) Human monocytes/macrophages: NO or no NO? J. Leuk. Biol. 55, 682-684.
17. Kuhl, S. J., and Rosen, H. (1995) Killing of microorganisms by 'professional phagocytes'. Curr. Opin. Infect. Dis. 8, 181-185.
18. DeGroote, M. A., and Fang, F. C. (1995) NO inhibitors: anti-microbial properties of nitric oxide. Clin. Infect. Dis. 21, S162-S164.
19. Beckman, 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 tyrosines in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler 375, 81-85.
20. Haddad, I. Y., Pataki, G., Hu, P., Galliani, C., Beckman, J. S., and Matalon, S. (1994) Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J. Clin. Invest. 94, 2407-2413.
21. Kaur, H., and Halliwell, B. (1994) Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. Nitro-tyrosine in serum and synovial fluid from rheumatoid patients. FEBS Lett. 350, 9-12.
22. Kooy, N. W., Royall, J. A., Ye, Y. Z., Kelly, D. R., and Beckman, J. S. (1995) Evidence of in vivo peroxynitrite production in human acute lung injury. Am. J. Respir. Crit. Care Med. 151, 1250-1254.
23. Dawson, V. L., Dawson, T. M., London, E. D., Bredt, D. S., and Snyder, S. H. (1991) Nitric oxide mediates glutamate neurotoxicity in primary cortical cultures. Proc. Natl. Acad. Sci. U.S.A., 88, 6368-6371.
24. Mulligan, M. S., Hevel, J. M., Marietta, M. A., and Ward, P. A. (1991) Tissue injury caused by deposition of immune complexes is L-arginine dependent. Proc. Natl. Acad. Sci. U.S.A., 88, 6338-6342.
25. Nowicki, J. P., Duval, D., Poignet, H., and Scatton, B. (1991) Nitric oxide mediates neuronal death after focal cerebral ischemia in the mouse. Eur. J. Pharmacol. 204, 339-340.
26. Matheis, G., Sherman, M. P., Buckberg, G. D., Haybron, D. M., Young, H. H., and Ignarro, L. J. (1992) Role of L-arginine-nitric oxide pathway in myocardial reoxygenation injury. Am. J. Physiol. 262, H616-H620.
27. Karupiah, G., Xie, Q., Buller, M. L., Nathan, C., Duarte, C., and MacMicking, J. D. (1993) Inhibition of viral replication by interferon-γ-induced nitric oxide synthase. Science 261, 1445-1448.
28. Stenger, S., Thuring, H., Rollinghoff, M., and Bogdan, C. (1994) Tissue expression of inducible nitric oxide synthase is closely associated with resistance to Leishmania major. J. Exp. Med. 180, 783-793.
29. MacMicking, J. D., Nathan, C., Horn, G., Chartrain, N., Fletcher, D. S., Trumbauer, M., Stevens, K., Xie, Q., Sokol, K., Hutchinson, N., Chen, H., and Mudgett, J. S. (1995) Altered responses to bacterial infection and endotoxic shock in mice lacking inducible nitric oxide synthase. Cell 81, 641-650.
30. Wei, X., Charles, I. G., Smith, A., Ure, J., Feng, G., Huang, F., Xu, D., Muller, W., Moncada, S., and Liew, F. Y. (1995) Altered immune responses in mice lacking inducible nitric oxide synthase. Nature 375, 408-411.
31. Lymar, S. V., and Hurst, J. K. (1995) Rapid reaction between peroxonitrite ion and carbon dioxide: implications for biological activity. J. Am. Chem. Soc. 117, 8877-8868.
32. Floris, R., Piersma, S. R., Yang, G., Jones, P., and Wever, R. (1993) Interaction of myeloperoxidase with peroxynitrite. A comparison with lactoperoxidase, horseradish peroxidase, and catalase. Eur. J. Biochem. 215, 767-775.
33. Lymar, S. V., and Hurst, J. K. (1996) Carbon dioxide: physiological catalyst for peroxynitrite-mediated cellular damage or cellular protectant? Chem. Res. Toxicol. 9, 845-850.
34. Lymar, S. V., Jiang, Q., and Hurst, J. K. (1996) Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 35, 7855-7861.
35. van der Vliet, A., O'Neill, C. A., Halliwell, B., Cross, C. E., and Kaur, H. (1994) Aromatic hydroxylation and nitration of phenylalanine and tyrosine by peroxynitrite. Evidence for hydroxyl radical production from peroxynitrite. FEBS Lett. 339, 89-92.
36. Zhu, L., Gunn, C., and Beckman, J. S. (1992) Bactericidal activity of peroxynitrite. Arch. Biochem. Biophys. 298, 452-457.
37. Elzanowska, H., Wolcott, R. G., Hannum, D. M., and Hurst, J. K. (1995) Bactericidal properties of hydrogen peroxide and copper or iron-containing complex ions in relation to leukocyte function. Free Radical Biol. Med. 18, 437-449.
38. Johnston, H. L., and Giauque, W. F. (1929) The heat capacity of nitric Oxide from 14 K to the boiling point and the heat of vaporization. J. Am. Chem. Soc. 51, 3194-3225.
39. Greenberg, A. E., Conners, J. J., and Jenkins D., Eds. (1981) Standard Methods for the Examination of Water and Wastewater, 15th ed., American Public Health Publications, Washington, DC.
40. Klebanoff, S. J., Waltersdorph, A. M., and Rosen, H. (1984) Antimicrobial activity of myeloperoxidase. Methods Enzymol. 105, 399-403.
41. Dertinger, H., and Jung, H. (1970) Molecular Radiation Biology, Springer-Verlag, New York.
42. Albrich, J. M., and Hurst, J. K. (1982) Oxidative inactivation of Escherichia coli by hypochlorous acid. Rates and differentiation of respiratory from other sites. FEBS Lett. 144, 157-161.
43. Leung, H. B., and Schramm, V. L. (1980) Adenylate degradation in Escherichia coli. The role of AMP nucleosidase and properties of the purified enzyme. J. Biol. Chem. 255, 10867-10874.
44. 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.
45. Inoue, S., and Kawanishi, S. (1995) Oxidative damage induced by simultaneous generation of nitric oxide and superoxide. FEBS Lett. 371, 86-88.
46. 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.
47. 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, L699-L722.
48. Goldstein, S., and Czapski, G. (1995) Direct and indirect oxidations by peroxynitrite. Inorg. Chem. 34, 4041-4048.
49. Edwards, J. O., and Plumb, R. C. (1994) The Chemistry of Peroxonitrites. Prog. Inorg. Chem. 41, 599-635.
50. Hurst, J. K., and Barrette, W. C., Jr. (1989) Leukocyte oxygen activation and microbial oxidative toxins. CRC Crit. Rev. Biochem. Mol. Biol. 24, 271-328.
51. Lymar, S. V., and Hurst, J. K. (1995) Role of compartmentation in promoting toxicity of leukocyte-generated strong oxidants. Chem. Res. Toxicol. 8, 833-840.
52. Klebanoff, S. J. (1993) Reactive nitrogen intermediates and antimicrobial activity: Role of nitrite. Free Radical Biol. Med. 14, 351-360.
53. Kono, Y., Shibata, H., Adachi, K., and Tanaka, K. (1994) Lactate-dependent killing of Escherichia coli by nitrite plus hydrogen peroxide: a possible role of nitrogen dioxide. Arch. Biochem. Biophys. 311, 153-159.
54. Anbar, M., and Taube, H. (1954) Interaction of nitrous acid with hydrogen peroxide. J. Am. Chem. Soc. 76, 6243-6247.
55. Brunelli, L., Crow, J. P., and Beckman, J. S. (1995) The comparative toxicity of nitric oxide and peroxynitrite to Escherichia coli. Arch. Biochem. Biophys. 316, 327-334.
56. Pacelli, R., Wink, D. A., Cook, J. A., Krishna, M. C., DeGraff, W., Friedman, N., Tsokos, M., Samuni, A., and Mitchell, J. B. (1995) Nitric oxide potentiates hydrogen peroxide-induced killing of Escherichia coli. J. Exp. Med. 182, 1469-1479.
57. Ioannidis, I., and DeGroot, H. (1993) Cytotoxicity of nitric oxide in Fu5 rat hematoma cells: evidence for co-operative action with hydrogen peroxide. Biochem. J. 296, 341-345.
58. Nathan, C. (1995) Natural resistance and nitric oxide. Cell 82, 873-876.
59. Vidal, S., Malo, D., Vogan, K., Skamene, E., and Gros, P. (1993) Natural resistance to infection with intracellular parasites: isolation of a candidate for Bcg. Cell 73, 469-485.
60. Segal, A. W., Geisow, M., Garcia, R., Harper, A., and Miller, R. (1981) The respiratory burst of phagocytic cells is associated with a rise in vacuolar pH. Nature 290, 406-409.
61. Cech, P., and Lehrer, R. I. (1984) Phagolysosomal pH of human neutrophils. Blood 63, 88-95.
62. Goldstein, S., and Czapski, G. (1996) Formation of peroxynitrite from the nitrosation of hydrogen peroxide by an oxygenated nitric oxide solution. Inorg. Chem. 35, 5935-5940.
63. Wolcott, R. G., Franks, B. S., Hannum, D. S., and Hurst, J. K. (1994) Bactericidal potency of hydroxyl radical in physiological environments. J. Biol. Chem. 269, 9721-9728.
64. Heimberger, A., and Eisenstark, A. (1988) Compartmentalization of catalases in Escherichia coli. Biochem. Biophys. Res. Commun. 154, 392-397.
65. Rubbo, H., Darley-Usmar, V., and Freeman, B. A. (1996) Nitric oxide regulation of tissue free radical injury. Chem. Res. Toxicol. 9, 809-820.
66. Tamir, S., Burney, S., and Tannenbaum, S. R. (1996) DNA damage by nitric oxide. Chem. Res. Toxicol. 9, 821-827.
67. Beckman, J. S. (1996) Oxidative damage and tyrosine nitration from peroxynitrite. Chem. Res. Toxicol. 9, 836-844.
68. 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.
69. Brown, G. C. (1995) Reversible binding and inhibition of catalase by nitric oxide. Eur. J. Biochem. 232, 188-191.
70. Asahi, M., Fujii, J., Suzuki, K., Seo, H. G., Kuzuya, T., Hori, M., Tada, M., Fujii, S., and Taniguchi, N. (1995) Inactivation of glutathione peroxidase by nitric oxide. Implication for cytotoxicity. J. Biol. Chem. 270, 21035-21039.