Reactions of peroxynitrite with γ-tocopherol

Chemical Research in Toxicology

Volumn 10, Issue 4, 1997, Pages 401-407

  Hoglen, Niel C ^a   Waller, Stephen C ^b   Sipes, I Glenn ^a   Liebler, Daniel C ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMAN DERIVATIVE; EDETATE IRON; GAMMA TOCOPHEROL; PEROXYNITRITE; QUINONE DERIVATIVE; SYDNONE DERIVATIVE; TOCOPHEROL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; NITRATION; OXIDATION;

MAGNETIC RESONANCE SPECTROSCOPY; MOLSIDOMINE; NITRATES; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, ULTRAVIOLET; VITAMIN E;

EID: 0030909437     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960200h     Document Type: Article

References (46)

1. Sheppard, A. J., Pennington, J. A. T., and Weihrauch, J. L. (1995) Analysis and distribution of vitamin E in vegetable oils and foods. In Vitamin E in health and disease (Packer, L., and Fuchs, J., Eds.) pp 95-144, Marcel Dekker, New York.
2. Machlin, L. J. (1991) Vitamin E. In Handbook of Vitamins, 2nd ed. (Machlin, L. J., Eds.) pp 95-144, Marcel Dekker, New York.
3. Burton, G. W., and Ingold, K. U. (1981) Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. J. Am. Chem. Soc. 103, 6472-6477.
4. Kaiser, S., Mascio, P. D., Murpghy, M. E., and Sies, H. (1990) Physical and chemical scavenging of singlet molecular oxygen by tocopherols. Arch. Biochem. Biophys. 277, 101-108.
5. Cooney, R. V., Franke, A. A., Harwood, P. J., Hatch-Pigott, V., Custer, L. J., and Mordan, L. J. (1993) γ-Tocopherol detoxification of nitrogen dioxide: Superiority to a-tocopherol. Proc. Natl. Acad. Sci. U.S.A. 90, 1771-1775.
6. Beckman, J. S., Beckman, T. W., Chen, J., and Marshall, P. A. (1990) Apparent hydroxyl radical production by peroxynitrite: Implications for endothelial injury from nintric oxide and superoxide. Proc. Natl. Acad. Sci. U.S.A. 87, 1620-1624.
7. Blough, N. V., and Zafiriou, O. C. (1985) Reaction of superoxide with nitric oxide to form peroxynitrite in alkaline aqueous solution. Inorg. Chem. 24, 3504-3505.
8. -. Free Radical Res. Commun. 18, 195-199.
9. Ischiropoulos, H., Zhu, L., and Beckman, J. S. (1992) Peroxynitrite formation from macrophage-derived nitric oxide. Arch. Biochem. Biophys. 298, 446-451.
10. Carreras, M. C., Pargament, G. A., Catz, S. D., Poderoso, J. J., and Boveris, A. (1994) Kinetics of nitric oxide and hydrogen peroxide production and formation of peroxynitrite during the respiratory burst of human neutrophils. FEBS Lett. 341, 65-68.
11. Spencer, J. P. E., Wong, J., Jenner, A., Aruoma, O. I., Cross, C. E., and Halliwell, B. (1996) Base modification and strand breakage in isolated calf DNA and in DNA from human skin epidermal keratinocytes exposed to peroxynitrite or 3-morpholinosydnonimine. Chem. Res. Toxicol. 9, 1152-1158.
12. 1-proteinase inhibitor by peroxynitrite. Chem. Res. Toxicol. 5, 425-431.
13. 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.
14. 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 tyrosine residues in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler 375, 81-88.
15. White, C. R., Brock, T. A., Chang, L. Y., Crapo, J., Briscoe, P., Ku, D., Bradley, W. A., Gianturco, S. H., Gore, J., and Freeman, B. A. (1994) Superoxide and peroxynitrite in atherosclerosis. Proc. Natl. Acad. Sci. U.S.A. 91, 1044-1048.
16. Haddad, I. Y., Pataki, G., Hu, P., Galliani, C., Beckman, J. B., 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.
17. Robertson, F. M., Long, B. W., Tober, K. L., Ross, M. S., and Oberyszyn, T. M. (1996) Gene expression and cellular sources of inducible nitric oxide synthase during tumor promotion. Carcinogenesis 17, 2053-2059.
18. 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. (Lung Cell. Mol. Physiol.) 268, L699-L722.
19. van der Vliet, A., O'Neill, C. A., Halliwell, B., Cross, C. E., and Kaur, H. (1993) Aromatic hydroxylation and nitration of phenylalanine and tyrosine by peroxynitrite. Evidence for hydroxyl radical production from peroxynitrite. FEBS Lett. 339, 89-92.
20. Koppenol, W. H., Moreno, J. J., Pryor, W. A., Ischiropoulos, H., and Beckman, J. S. (1992) Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide. Chem. Res. Toxicol. 5, 834-842.
21. 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.
22. Ischiropoulos, H., Zhu, L., Chen, J., Tsai, M., Martin, J. C., Smith, C. D., and Beckman, J. S. (1992) Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 298, 431-437.
23. Beckman, J. S. (1996) Oxidative damage and tyrosine nitration from peroxynitrite. Chem. Res. Toxicol. 9, 836-844.
24. 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.
25. de Groot, H., Hegi, U., and Sies, H. (1993) Loss of α-tocopherol upon exposure to nitric oxide or the sydnonimine, SIN-1. FEBS Lett. 315, 139-142.
26. Hogg, N., Joseph, J., and Kalyanaraman, B. (1994) The oxidation of α-tocopherol and Trolox by peroxynitrite. Arch. Biochem. Biophys. 314, 153-158.
27. Beckman, J. S., Chen, J., Ischiropoulos, H., and Crow, J. P. (1994) Oxidative chemistry of Peroxynitrite. Methods Enzymol. 233, 229-240.
28. Liebler, D. C., and Burr, J. A. (1992) Oxidation of vitamin E during iron-catalyzed lipid peroxidation: evidence for electron-transfer reactions of the tocopheroxyl radical. Biochemistry 31, 8278-8284.
29. Liebler, D. C., Kayson, K. L., and Kennedy, T. A. (1989) Redox cycles of vitamin E: hydrolysis and ascorbic acid dependent reduction of 8a-(alkyldioxy)tocopherones. Biochemistry 28, 9772-9777.
30. 2 and their formation in rat insulinoma (RINm5F) cells. Free Radical Biol. Med. 19, 259-269.
31. Yamauchi, R., Matsui, T., Kato, K., and Uend, Y. (1990) Reaction products of γ-tocopherol with an alkylperoxyl radical in benzene. Agric. Biol. Chem. 54, 2703-2709.
32. Yamauchi, R., and Matsushita, S. (1979) Products formed by photosensitized oxidation of tocopherols. Agric. Biol. Chem. 43, 2151-2156.
33. Durckheimer, W., and Cohen, L. A. (1964) The chemistry of 9-hydroxy-alpha-tocopherone, a quinone hemi-acetal. J. Am. Chem. Soc. 86, 4388-4393.
34. Goodhue, C. T., and Risley, H. A. (1965) Reactions of vitamin E with peroxides. II. Reaction of benzoyl peroxide with d-alpha-tocopherol in alcohols. Biochemistry 4, 854-858.
35. Spencer, J. P. E., Wong, J., Jenner, A., Aruoma, O. I., Cross, C. E., and Halliwell, B. (1996) Base modification and strand breakage in isolated calf thymus DNA and in DNA from human skin epidermal keratinocytes exposed to peroxynitrite or 3-morpholinosydnonimine. Chem. Res. Toxicol. 9, 1152-1158.
36. Burton, G. W., and Ingold, K. U. (1986) Vitamin E: application of the principles of physical organic chemistry to the exploration of its structrure and function. Acc. Chem. Res. 19, 194-201.
37. Liebler, D. C. (1993) The role of metabolism in the antioxidant function of vitamin E. Crit. Rev. Toxicol. 23, 147-169.
38. van der Vliet, A., Eiserich, J. P., O'Neill, C. A., Halliwell, B., and Cross, C. E. (1995) Tyrosine modification by reaction nitrogen species: a closer look. Arch. Biochem. Biophys. 319, 341-349.
39. Ramezanian, M. S., Padmaja, S., and Koppenol, W. H. (1996) Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chem. Res. Toxicol. 9, 232-240.
40. Liebler, D. C., Baker, P. F., and Kayson, K. L. (1990) Oxidation of vitamin E: Evidence for competing autoxidation and peroxyl radical trapping reactions of the tocopheroxyl radical. J. Am. Chem. Soc. 112, 6995-7000.
41. Yamauchi, R., Yagi, Y., and Kato, K. (1994) Isolation and characterization of addition products of a-tocopherol with peroxyl radicals of dilinoleoylphatidylcholine in liposomes. Biochim. Biophys. Acta 1212, 43-49.
42. Goodhue, C. T., and Risley, H. A. (1965) Reactions of vitamin E with peroxides. II. reaction of benzoyl peroxide with d-alpha-tocopherol in alcohols. Biochemistry 4, 854-858.
43. Uppu, R. M., Squadito, G. L., and Pryor, W. A. (1996) Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 327, 335-343.
44. 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.
45. Gow, A., Duran, D., Thom, S. R., and Ischiropoulos, H. (1996) Carbon dioxide enhancement of peroxynitrite-mediated protein tyrosine nitration. Arch. Biochem. Biophys. 333, 42-48.
46. Denicola, A., Freeman, B. A., Trujillo, M., and Radi, R. (1996) Peroxynitrite reaction with carbon dioxide/bicarbonate: Kinetics and influence of peroxynitrite-mediated oxidations. Arch. Biochem. Biophys. 333, 49-58.