Kinetic Analysis of Intracellular Concentrations of Reactive Nitrogen Species

Chemical Research in Toxicology

Volumn 21, Issue 11, 2008, Pages 2134-2147

  Chang, Hoon Lim ^a   Dedon, Peter C ^a   Deen, William M ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 NITROTYROSINE; AMINO ACID; ANTIOXIDANT; ASCORBIC ACID; CARBON DIOXIDE; CELL PROTEIN; GLUTATHIONE; LIPID; NITRIC OXIDE; NITRITE; NITROGEN DIOXIDE; PEROXYNITRITE; REACTIVE NITROGEN SPECIES; S NITROSOGLUTATHIONE; TYROSINE DERIVATIVE;

ARTICLE; CONCENTRATION RESPONSE; HYDROPHOBICITY; INFLAMMATION; KINETICS; OXIDATION; STEADY STATE;

GLUTATHIONE; HYDROXYL RADICAL; KINETICS; MODELS, BIOLOGICAL; NITRIC OXIDE; REACTIVE NITROGEN SPECIES; S-NITROSOGLUTATHIONE; TYROSINE;

EID: 57449110511     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx800213b     Document Type: Article

References (71)

1. Moncada, S., Palmer, R. M. J., and Higgs, E. A. (1991) Nitric oxide: Physiology, pathophysiology and pharmacology. Pharmacol. Rev. 43, 109-142.
2. Tamir, S., Burney, S., and Tannenbaum, S. R. (1996) DNA damage by nitric oxide. Chem. Res. Toxicol. 9, 821-827.
3. Lewis, R. S., Tamir, S., and Deen, W. M. (1995) Kinetic analysis of the fate of nitric oxide synthesized by macrophages in vitro. J. Biol. Chem. 270, 29350-29355.
4. deRojas-Walker, T., Tamir, S., Ji, H., Wishnok, J. S., and Tannenbaum, S. R. (1995) Nitric oxide induces oxidative damage in addition to deamination in macrophage DNA. Chem. Res. Toxicol. 8, 473-477.
5. Tamir, S., and Tannenbaum, S. R. (1996) The role of nitric oxide in the carcinogenic process. Biochim. Biophys. Acta 1288, F31-F36.
6. Nalwaya, N., and Deen, W. M. (2003) Analysis of cellular exposure to peroxynitrite in suspension cultures. Chem. Res. Toxicol. 16, 920-932.
7. Lancaster, J. R., Jr. (2006) Nitroxidative, nitrosative, and nitrative stress: Kinetic predictions of reactive nitrogen species chemistry under biological conditions. Chem. Res. Toxicol. 19, 1160-1174.
8. 2 within the hydrophobic interior of biological membranes. Proc. Natl. Acad. Sci. U.S.A. 95, 2175-2179.
9. 2 reaction. Chem. Res. Toxicol. 20, 709-714.
10. Prutz, W. A., Monig, H., Butler, J., and Land, E. J. (1985) Reactions of nitrogen dioxide in aqueous model systems: Oxidation of tyrosine units in peptides and proteins. Arch. Biochem. Biophys. 243, 125-134.
11. Kikugawa, K., Kato, T., and Okamoto, Y. (1994) Damage of amino acids and proteins induced by nitrogen dioxide, a free radical toxin, in air. Free Radical Biol. Med. 16, 373-382.
12. Lewis, R. S., and Deen, W. M. (1994) Kinetics of the reaction of nitric oxide with oxygen in aqueous solutions. Chem. Res. Toxicol. 7, 568-574.
13. Schwartz, S. E. (1969) Trace atmospheric constituents: Properties, transformations, and fates. Advances in Environmental Science and Technology, pp 1-115, Wiley, New York.
14. Ross, A. B., Mallard, W. G., Helman, W. P., Buxton, G. V., Hurie, R. E., and Neta, P. (1998) NDRL/NIST Solution Kinetics Database, version 3, Notre Dame Radiation Laboratory, Gaithersburg, MD, http://www.rcdc.nd.edu/ browse_compil.html.
15. - under physiological conditions. How the radicals do the job. J. Biol. Chem. 275, 3031-3036.
16. Ford, E., Hughes, M. N., and Wardman, P. (2002) Kinetics of the reactions of nitrogen dioxide with glutathione, cysteine, and uric acid at physiological pH. Free Radical Biol. Med 32, 1314-1323.
17. Kirsch, M., Lehnig, M., Korth, H.-G., Sustmann, R., and de Groot, H. (2001) Inhibition of peroxynitrite-induced nitration of tyrosine by glutathione in the presence of carbon dioxide through both radical repair and peroxynitrite formation. Chem. Eur. J. 15, 3313-3320.
18. Hoffman, M., and Hayon, E. (1973) Pulse radiolysis study of sulfhydryl compounds in aqueous solution. J. Phys. Chem. 77, 990-996.
19. Wardman, P., and von Sonntag, C. (1995) Kinetic factors that control the fate of thiyl radicals in cells. Methods Enzymol. 251, 31-45.
20. Wood, P. D., Mutus, B., and Redmond, R. W. (1996) The mechanism of photochemical release of nitric oxide from S-nitrosoglutathione. Photochem. Photobiol. 64, 518-524.
21. Shin, H. W., and George, C. (2001) Steven. Microscopic modeling of NO and S-nitrosoglutathione kinetics and transport in human airways. J. Appl. Physiol. 90, 777-788.
22. Jourd'heuil, D., Mai, C. T., Laroux, F. S., Wink, D. A., and Grisham, M. B. (1998) The reaction of S-nitrosoglutathione with superoxide. Biochem. Biophys. Res. Commun. 246, 525-530.
23. 2 and NO in aqueous solution: Intermediacy of organicperoxynitrate and peroxynitrite species. J. Phys. Chem. 108, 1719-1725.
24. Wardman, P. (1998) Evaluation of the 'radical sink' hypothesis from a chemical-kinetic viewpoint J. Radioanal. Nucl. Chem. 232, 23-27.
25. Keshive, M., Singh, S., Wishnok, J. S., Tannenbaum, S. R., and Deen, W. M. (1996) Kinetics of S-nitrosation of thiols in nitric oxide solutions. Chem. Res. Toxicol. 9, 988-993.
26. Bonini, M. G., and Augusto, O. (2001) Carbon dioxide stimulates the production of thiyl, sulfinyl and disulfide radical anion from thiol oxidation by peroxynitrite. J. Biol. Chem. 276, 9749-9754.
27. Chen, S. N., and Hoffman, M. Z. (1973) Rate constants for the reaction of the carbonate radical with compounds of biochemical interest in neutral aqueous solution. Radiat. Res. 56, 40-47.
28. Jones, C. M., Lawrence, A., Wardman, P., and Burkitt, M. J. (2003) Kinetics of superoxide scavenging by glutathione: An evaluation of its role in the removal of mitochondrial superoxide. Biochem. Soc. Trans. 31, 1337-1339.
29. Luo, D., Smith, S. W., and Anderson, B. D. (2005) Kinetics and mechanism of the reaction of cysteine and hydrogen peroxide in aqueous solution. J. Pharm. Sci. 94, 304-316.
30. Quijano, C., Romero, N., and Radi, R. (2005) Tyrosine nitration by superoxide and nitric oxide fluxes in biological systems: modeling the impact of superoxide dismutase and nitric oxide diffusion. Free Radical Biol. Med. 39, 728-741.
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, 8867-8868.
32. Behar, D., Czapski, G., and Duchovny, I. (1970) Carbonate radical in flash photolysis and pulse radiolysis of aqueous carbonate solutions. J. Phys. Chem. 74, 2206-2210.
33. Czapski, G., Holcman, J., and Bielski, B. H. (1994) Reactivity of nitric oxide with simple short-lived radicals in aqueous solutions. J. Am. Chem. Soc. 116, 11465-11469.
34. Solar, S., Solar, W., and Getoff, N. (1984) Reactivity of OH with tyrosine in aqueous solution studied by pulse radiolysis. J. Phys. Chem. 88, 2091-2095.
35. Hudges, G. R., Marwaha, J., Paul, T., and Ingold, K. U. (2000) A novel procedure for generating both nitric oxide and superoxide in situ from chemical sources at any chosen mole ratio. First application: Tyrosine oxidation and a comparison with performed peroxynitrite. Chem. Res. Toxicol. 13, 1287-1293.
36. - toward NADH. Chem. Res. Toxicol. 13, 736-741.
37. Jourd'heuil, D., Jourd'heuil, F. L., Kutchukian, P. S., Musah, R. A., Wink, D. A., and Grisham, M. B. (2001) Reaction of superoxide and nitric oxide with peroxynitrite. Implications for peroxynitrite-mediated oxidation reactions in vivo. J. Biol. Chem. 276, 28799-28805.
38. Santos, C., Bonini, M. G., and Augusto, O. (2000) Role of the carbonate anion in tyrosine nitration and hydroxylation by peroxynitrite. Arch. Biochem. Biophys. 377, 146-152.
39. Buxton, G. V., and Elliot, A. J. (1986) Rate-constant for the reaction of hydroxyl radical with bicarbonate ions. Radiat. Phys. Chem. 27, 241-243.
40. Alvarez, B., and Radi, R. (2003) Peroxynitrite reactivity with amino acids and proteins. Amino Acids 25, 295-311.
41. 2: A pulse radiolysis study. Free Radical Biol. Med. 19, 505-510.
42. Gratzel, M., Henglein, A., Lilie, J., and Beck, G. (1969) Pulsradiolytische Untersuchung einigerelementarprozesse der oxidation und reduction des nitritions. Ber. Bunsenges. Phys. Chem. 73, 646-653.
43. 3 solutions. Bull Acad. Pol. Sci. Sedr. Sci. Chim. 24, 221-229.
44. Schwartz, S. E., and White, W. H. (1983) Kinetics of reactive dissolution of nitrogen oxide in aqueous solution. Adv. Environ. Sci. Technol. 12, 1-116.
45. Hunter, E. P. L., Desrosiers, M. F., and Simic, M. G. (1989) The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization. Free Radical Biol. Med. 6, 581-585.
46. Roos, A., and Boron, W. F. (1981) Intracellular pH. Physiol. Rev. 61, 296-434.
47. Bergstrom, J., Furst, P., Noree, L. O., and Vinnars, E. (1974) Intracellular free amino acid concentration in human muscle tissue. J. Appl. Physiol. 36, 693-697.
48. Fritsche, E., Schäfer, C., Calles, C., Bemsmann, T., Bernshausen, T., Wurm, M., Hübenthal, U., Cline, J. E., Hajimiragha, H., Schroeder, P., Klotz, L. O., Rannug, A., Fürst, P., Hanenberg, H., Abel, J., and Krutmann, J. (2007) Lightening up the UV response by identification of the arylhydrocarbon receptor as a cytoplasmatic target for ultraviolet B radiation. Proc. Natl. Acad. Sci. U.S.A. 104, 8851-8856.
49. Leo, A., Hoekman, D. H., and Hansen, C. (1995) Exploring QSAR, American Chemical Society, Washington, DC.
50. Meylan, W. M., and Howard, P. H. (1995) Atom/fragment contribution method for estimating octanol-water partition coefficients. J. Pharm. Sci. 84, 83-92.
51. Hansen, J. M., Go, Y. M., and Jones, D. P. (2006) Nuclear and mitochondrial compartmentation of oxidative stress and redox signaling. Annu. Rev. Pharmacol. Toxicol. 46, 215-234.
52. Garcia-Ruiz, C., Morales, A., Ballesta, A., Rodes, J., Kaplowitz, N., and Fernandez-Checa, J. C. (1994) Effect of chronic ethanol feeding on glutathione and functional integrity of mitochondria in periportal and perivenous rat hepatocytes. J. Clin. Invest. 94, 193-201.
53. Goldstein, S., and Czapski, G. (1996) Mechanism of the nitrosation of thiols and amines by oxygenated NO solutions: The nature of the nitrosating intermediates. J. Am. Chem. Soc. 118, 3419-3425.
54. -. Free Radical Biol. Med. 34, 1078-1088.
55. Sovitj, P., and Rose, G. M. (1998) Generation of thiyl radical by nitric oxide: a spin trapping study. J. Chem. Soc., Perkins Trans 2 1507-1512.
56. Jourd'heuil, D., Jourd'heuil, F. L., and Feelisch, M. (2003) Oxidation and nitrosation of thiols at low micromolar exposure to nitric oxide. J. Biol. Chem. 278, 15720-15726.
57. Radi, R. (2004) Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl. Acad. Sci. U.S.A. 101, 4003-4008.
58. Kluge, I., Gutteck-Amsier, U., Zollinger, M., and Quang Do, K. (1997) S-nitrosoglutathione in rat cerebellum: Identification and quantification by liquid chromatography-mass spectrometry. J. Neurochem. 69, 2599-2607.
59. Stamler, J. S., Jaraki, O., Osborne, J., Simon, D. I., Keaney, J., Vita, J., Singeli, D., Valeri, C. R., and Loscalzo, J. (1992) Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin. Proc. Natl. Acad. Sci. U.S.A. 89, 7674-7677.
60. Gaston, B., Reilly, J., Drazen, J. M., Fackler, J., Ramdev, P., Arnelle, D., Mullins, M. E., Sugarbaker, D. J., Chee, C., Singel, D. J., Loscalzo, J., and Stamler, J. S. (1993) Endogenous nitrogen oxides and bronchiolar S-nitrosothiols in human airways. Proc. Natl Acad. Sci. U.S.A. 90, 10957-10961.
61. Washko, P., Rotrosen, D., and Levine, M. (1989) Ascorbic acid transport and accumulation in human neutrophils. J. Biol. Chem. 264, 18996-19002.
62. Zhang, H., Joseph, J., Felix, C., and Kalyanaraman, B. (2000) Bicarbonate enhances the hydroxylation, nitration and peroxidation reactions catalyzed by copper, zinc superoxide dismutase. J. Biol. Chem. 275, 14038-14045.
63. Ramirez, D. C., Mejiba, S. E. C., and Mason, R. P. (2005) Mechanism of hydrogen peroxide-induced Cu, Zn-superoxide dismutase-centered radical formation as explored by immuno-spin trapping: the role of copper and carbonate radical anion-mediated oxidations. Free Radical Biol. Med. 38, 201-214.
64. Karunakaran, C., Zhang, H., Joseph, J., Antholine, W. E., and Kalyanaraman, B. (2005) Thiol oxidase activity of copper, zinc superoxide dismutase stimulates bicarbonate-dependent peroxidase activity via formation of a carbonate radical. Chem. Res. Toxicol. 18, 494-500.
65. Halliwell, B., and Gutteridge, J. M. C., Eds. (1998) Free Radicals in Biology and Medicine, Oxford University Press, Oxford.
66. Burner, U., Furtmüller, P. G., Kettle, A. J., Koppenol, W. H., and Obinger, C. (2000) Mechanism of reaction of myeloperoxidase with nitrite. J. Biol. Chem. 275, 20597-20601.
67. Nguyen, T., Brunson, D., Crespi, C. L., Penman, B., 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.
68. Traut, T. W. (1994) Physiological concentrations of purines and pyrimidines. Mol. Cell. Biochem. 140, 1-22.
69. Li, C. Q., Wright, T. L., Dong, M., Dommels, Y. E., Trudel, L. J., Dedon, P. C., Tannenbaum, S. R., and Wogan, G. N. (2005) Biological role of glutathione in nitric oxide-induced toxicity in cell culture and animal models. Free Radical Biol. Med. 39, 1489-1498.
70. Dong, M., Wang, C., Deen, W. M., and Dedon, P. C. (2003) Absence of 2-deoxyoxanosine and presence of abasic sites in DNA exposed to nitric oxide at controlled physiological concentrations. Chem. Res. Toxicol. 16, 1044-1055.
71. Dong, M., and Dedon, P. C. (2006) Relatively small increases in the steady-state levels of nucleobase deamination products in DNA from human TK6 cells exposed to toxic levels of nitric oxide. Chem. Res. Toxicol. 19, 50-57.