4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (Tempol) inhibits peroxynitrite-mediated phenol nitration

Chemical Research in Toxicology

Volumn 13, Issue 4, 2000, Pages 294-300

  Carroll, Richard T ^a   Galatsis, Paul ^a   Borosky, Susan ^a   Kopec, Karla K ^a   Kumar, Vikram ^a   Althaus, John S ^a   Hall, Edward D ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLAMINE; PEROXYNITRITE; PHENOL; TEMPOL;

ANIMAL CELL; ARTICLE; CATALYSIS; DECOMPOSITION; HYDROXYLATION; INHIBITION KINETICS; NITRATION; NONHUMAN; OXIDATION REDUCTION REACTION; PH;

ANIMALS; ANTIOXIDANTS; CYCLIC N-OXIDES; HYDROGEN-ION CONCENTRATION; HYDROXYLATION; L-LACTATE DEHYDROGENASE; MOLSIDOMINE; NITRATES; NITRO COMPOUNDS; NITROSO COMPOUNDS; PC12 CELLS; PHENOL; RATS; SPIN LABELS;

ANIMALIA; LETHRINIDAE;

EID: 0034055967     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990159t     Document Type: Article

References (39)

1. 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 (4), 1620-4.
2. Kissner, R., Nauser, T., Bugnon, P., Lye, P. G., and Koppenol, W. H. (1997) Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis. Chem. Res. Toxicol. 10 (11), 1285-92 [published erratum, (1998) Chem. Res. Toxicol. 11 (5), 557].
3. Denicola, A., Souza, J. M., and Radi, R. (1998) Diffusion of peroxynitrite across erythrocyte membranes. Proc. Natl. Acad. Sci. U.S.A. 95 (7), 3566-71.
4. Radi, R. (1998) Peroxynitrite reactions and diffusion in biology. Chem. Res. Toxicol. 11 (7), 720-1.
5. 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 (1-2), 89-92.
6. 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 (23), 11173-7.
7. Dowell, F. J., and Martin, W. (1998) Interaction between peroxynitrite and L-cysteine: effects on rat aorta. Eur. J. Pharmacol. 344 (2-3), 183-90.
8. Inoue, S., and Kawanishi, S. (1995) Oxidative DNA damage induced by simultaneous generation of nitric oxide and superoxide. FEBS Lett. 371 (1), 86-8.
9. 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 (3), 1025-30.
10. 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 (3), 207-10.
11. Good, P. F., Werner, P., Hsu, A., Olanow, C. W., and Perl, D. P. (1996) Evidence of neuronal oxidative damage in Alzheimer's disease. Am. J. Pathol. 149 (1), 21-8.
12. Hensley, K., Maidt, M. L., Yu, Z., Sang, H., Markesbery, W. R., and Floyd, R. A. (1998) Electrochemical analysis of protein nitrotyrosine and dityrosine in the Alzheimer brain indicates region-specific accumulation. J. Neurosci. 18 (20), 8126-32.
13. Koppal, T., Drake, J., Yatin, S., Jordan, B., Varadarajan, S., Bettenhausen, L., and Butterfield, D. A. (1999) Peroxynitrite-induced alterations in synaptosomal membrane proteins: insight into oxidative stress in Alzheimer's disease. J. Neurochem. 72 (1), 310-7.
14. Paris, D., Parker, T. A., Town, T., Sue, Z., Fang, C., Humphrey, J., Crawford, F., and Mullan, M. (1998) Role of peroxynitrite in the vasoactive and cytotoxic effects of Alzheimer's beta-amyloid1-40 peptide. Exp. Neurol. 152 (1), 116-22.
15. Smith, M. A., Richey Harris, P. L., Sayre, L. M., Beckman, J. S., and Perry, G. (1997) Widespread peroxynitrite-mediated damage in Alzheimer's disease. J. Neurosci. 17 (8), 2653-7.
16. Su, J. H., Deng, G., and Cotman, C. W. (1997) Neuronal DNA damage precedes tangle formation and is associated with up-regulation of nitrotyrosine in Alzheimer's disease brain. Brain Res. 774 (1-2), 193-9.
17. Cross, A. H., Manning, P. T., Keeling, R. M., Schmidt, R. E., and Misko, T. P. (1998) Peroxynitrite formation within the central nervous system in active multiple sclerosis, J. Neuroimmunol. 88 (1-2), 45-56.
18. Gurwitz, D., and Kloog, Y. (1998) Peroxynitrite generation might explain elevated glutamate and aspartate levels in multiple sclerosis cerebrospinal fluid [letter]. Eur. J. Clin. Invest. 28 (9), 760-1.
19. Hooper, D. C., Bagasra, O., Marini, J. C., Zborek, A., Ohnishi, S. T., Kean, R., Champion, J. M., Sarker, A. B., Bobroski, L., Farber, J. L., Akaike, T., Maeda, H., and Koprowski, H. (1997) Prevention of experimental allergic encephalomyelitis by targeting nitric oxide and peroxynitrite: implications for the treatment of multiple sclerosis. Proc. Natl. Acad. Sci. U.S.A. 94 (6), 2528-33.
20. Hooper, D. C., Spitsin, S., Kean, R. B., Champion, J. M., Dickson, G. M., Chaudhry, I., and Koprowski, H. (1998) Uric acid, a natural scavenger of peroxynitrite, in experimental allergic encephalo-myelitis and multiple sclerosis. Proc. Natl. Acad. Sci. U.S.A. 95 (2), 675-80.
21. Mesenge, C., Charriaut Marlangue, C., Verrecchia, C., Allix, M., Boulu, R. R., and Plotkine, M. (1998) Reduction of tyrosine nitration after N-(omega)-nitro-L-arginine-methylester treatment of mice with traumatic brain injury. Eur. J. Pharmacol. 353 (1), 53-7.
22. Coeroli, L., Renolleau, S., Arnaud, S., Plotkine, D., Cachin, N., Plotkine, M., Ben Ari, Y., and Charriaut Marlangue, C. (1998) Nitric oxide production and perivascular tyrosine nitration following focal ischemia in neonatal rat. J. Neurochem. 70 (6), 2516-25.
23. 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 (2-3), 229-32.
24. Fukuyama, N., Takizawa, S., Ishida, H., Hoshiai, K., Shinohara, Y., and Nakazawa, H. (1998) Peroxynitrite formation in focal cerebral ischemia-reperfusion in rats occurs predominantly in the peri-infarct region. J. Cereb. Blood Flow Metab. 18 (2), 123-9.
25. Beckman, J. S., Carson, M., Smith, C. D., and Koppenol, W. H. (1993) ALS, SOD and peroxynitrite [letter]. Nature 364 (6438), 584.
26. Landino, L. M., Crews, B. C., Timmons, M. D., Morrow, J. D., and Marnett, L. J. (1996) Peroxynitrite, the coupling product of nitric oxide and superoxide, activates prostaglandin biosynthesis. Proc. Natl. Acad. Sci. U.S.A. 93, 15069-74.
27. Denicola, A., Freeman, B. A., Trujillo, M., and Radi, R. (1996) Peroxynitrite reaction with carbon dioxide/bicarbonate: kinetics and influence on peroxynitrite-mediated oxidations. Arch. Biochem. Biophys. 333 (1), 49-58.
28. Davenport, H. W. (1974) The ABC of Acid-Base Chemistry, 6th ed., The University of Chicago Press, Chicago.
29. Radi, R., Denicola, A., and Freeman, B. A. (1999) Peroxynitrite reactions with carbon dioxide-bicarbonate. Methods Enzymol. 301, 353-67.
30. Uppu, R. M., Squadrito, G. L., and Pryor, W. A. (1996) Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 327 (2), 335-43.
31. Gow, A., Duran, D., Thorn, S. R., and Ischiropoulos, H. (1996) Carbon dioxide enhancement of peroxynitrite-mediated protein tyrosine nitration. Arch. Biochem. Biophys. 333 (1), 42-8.
32. Uppu, R. M., Squadrito, G. L., Cueto, R., and Pryor, W. A. (1996) Synthesis of peroxynitrite by azide-ozone reaction. Methods Enzymol. 269, 311-21.
33. Beckman, J. S., Ischiropoulos, H., Zhu, L., van der Woerd, M., Smith, C., Chen, J., Harrison, J., Martin, J. C., andTsai, M. (1992) Kinetics of superoxide dismutase-and iron-catalyzed nitration of phenolics by peroxynitrite. Arch. Biochem. Biophys. 298 (2), 438-45.
34. Lemercier, J. N., Padmaja, S., Cueto, R., Squadrito, G. L., Uppu, R. M., and Pryor, W. A. (1997) Carbon dioxide modulation of hydroxylation and nitration of phenol by peroxynitrite. Arch. Biochem. Biophys. 345 (1), 160-70.
35. Griess, J. P. (1864) On a new series of bodies in which nitrogen is substituted for hydrogen. Philos. Trans. R. Soc. London 154, 667-731.
36. Estevez, A. G., Radi, R., Barbeito, L., Shin, J. T., Thompson, J. A., and Beckman, J. S. (1995) Peroxynitrite-induced cytotoxicity in PC12 cells: evidence for an apoptotic mechanism differentially modulated by neurotrophic factors. J. Neurochem. 65 (4), 1543-50.
37. Hogg, N., Darley Usmar, V. M., Wilson, M. T., and Moncada, S. (1992) Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. Biochem. J. 281 (Part 2). 419-24.
38. Mitchell, J. B., Samuni, A., Krishna, M. C., DeGraff, W. G., Ahn, M. S., Samuni, U., and Russo, A. (1990) Biologically active metal-independent superoxide dismutase mimics. Biochemistry 29 (11), 2802-7.
39. Samuni, A., Krishna, C. M., Mitchell, J. B., Collins, C. R., and Russo, A. (1990) Superoxide reaction with nitroxides. Free Radical Res. Commun. 9 (3-6), 241-9.