Phenolic Antioxidants Prevent Peroxynitrite-Derived Collagen Modification in Vitro

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 8, 1997, Pages 3004-3009

  Kato, Yoji ^a   Ogino, Yuji ^a   Aoki, Tomoko ^a   Uchida, Koji ^a   Kawakishi, Shunro ^a   Osawa, Toshihiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Antibody; Antioxidants; Collagen; Nitrotyrosine; Peroxynitrite

Indexed keywords

EID: 0000171328     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf960865p     Document Type: Article

References (27)

1. Beckman, J. S.; Ye, Y. Z.; Anderson, P. G.; Chen, J.; Accavitti, M. A.; Tarpey, M. M.; White, C. R. Extensive nitration of protein tyrosines in human atherosclerosis detection by immunohistochemistry. Biol. Chem. Hoppe-Seyler 1994, 375, 81-88.
2. Crow, J. P.; Beckman, J. S. The role of peroxynitrite in nitric oxide-mediated toxicity. Curr. Top. Microbiol. Immunol. 1995, 196, 57-73.
3. Domigan, N. M.; Charlton, T. S.; Duncan, M. W.; Witerbourn, C. C.; Kettle, A. J. Chlorination of tyrosyl residues in peptides by myeloperoxidase and human neutrophils. J. Biol. Chem. 1995, 270, 16542-16548.
4. Frears, E. R.; Zhang, Z.; Blake, D. R.; O'Connell, J. P. O.; Winyard, P. G. Inactivation of tissue inhibitor of metallo-proteinase-1 by peroxynitrite. FEBS Lett. 1996, 381, 21-24.
5. Haddad, I. Y.; Pataki, G.; Hu, P.; Galliani, C.; Beckman, J. S.; Matalon, S. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J. Clin. Invest. 1994, 94, 2407-2413.
6. Hughes, M. N.; Nicklin, H. G. The chemistry of pernitrites. Part II. Kinetics of decomposition of pernitrous acid. J. Chem. Soc. A 1968, 450-452.
7. Hughes, M. N.; Nicklin, H. G. The chemistry of peroxonitrites. Part II. Copper(II)-catalyzed reaction between hydroxylamine and peroxonitrite in alkali. J. Chem. Soc. A 1970, 925-928.
8. Ischiropoulos, H.; Zhu, L.; Chen, J.; Tsai, M.; Martin, J. C.; Smith, C. D.; Beckman, J. S. Peroxynitrite-modified tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 1992, 298, 431-437.
9. Ischiropoulos, H.; Al-Mehidi, A. B.; Fisher, A. B. Reactive species in ischemic rat lung injury: contribution of peroxynitrite. Am. J. Physiol: Lung Cell. Mol. Physiol. 13 1995a, 269, L158-L164.
10. Ischiropoulos, H.; Al-Mehdi, A. B. Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 1995b, 364, 279-282.
11. Kato, Y.; Nishikawa, T.; Kawakishi, S. Formation of protein-bound 3,4-dihydroxyphenylalanine in collagen types I and IV exposed to ultraviolet light. Photochem. Photobiol. 1995, 67, 367-372.
12. 2. J. Biol. Chem. 1992, 267, 23646-23651.
13. Kato, Y.; Uchida, K.; Kawakishi, S. Aggregation of collagen exposed to UVA in the presence of riboflavin: a plausible role for tyrosine modification. Photochem. Photobiol. 1994, 59, 343-349.
14. Kaur, H.; Halliwell, B. Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. Nitrotyrosine in serum and synovial fluid from rheumatoid patients. FEBS Lett. 1994, 350, 9-12.
15. King, S.-K.; Yim, M. B.; Stadtman, E. R.; Chock, P. B. Peroxynitrite disables the tyrosine phosphorylation regulatory mechanism: Lymphocyte-specific tyrosine kinase fails to phosphorylate nitrated cdc 2(6-26)NH2 peptide. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 3377-3382.
16. Laemmli, U. K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970, 227, 680-685.
17. Mannick, E. E.; Bravo, L. E.; Zarama, G.; Realpe, J. L.; Zhang, X.-J.; Ruiz, B.; Fontham, E. T. H.; Mera, R.; Miller, M. J. S.; Correa, P. Inducible nitric oxide synthase, nitrotyrosine, and apoptosis in Hericobacter pyroli gastritis: Effect of antibiotics and antioxidants. Cancer Res. 1996, 56, 3238-3243.
18. Mozhaev, V. V.; Siksnis, V. A.; Melik-Nubarov, N. S.; Galkantaite, N. Z.; Denis, G. J.; Butkus, E. P.; Zaslavsky, B. Y.; Mestechkina, N. M.; Martinek, K. Protein stabilization via hydrophilization. Covalent modification of trypsin and α-chymotrypsin. Eur. J. Biochem. 1988, 173, 147-154.
19. Salman-Tabcheh, S.; Guerin, M.-C.; Torreilles, J. Nitration of tyrosyl-residues from extra- and intracellular protein in human whole blood. Free Radicals Biol. Med. 1995, 19, 695-698.
20. Skinner, K. A.; Tan, S.; Parks, D. A. Peroxynitrite-mediated oxidation of uric acid, allantoin and parabanic acid: potential induces of oxidant stress. FASEB J. Abstr. 1995, A325, 1884.
21. Sugiyama, Y.; Kawakishi, S.; Osawa, T. Involvement of the β-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin. Biochem. Pharmacol. 1996, 52, 519-525.
22. Szabó, C.; Salzman, A. L.; Ischiropoulos, H. Endotoxin triggers the expression of an inducible isoform of nitric oxide synthase and the formation of peroxynitrite in the rat aorta in vivo. FEBS Lett. 1995a, 363, 235-238.
23. Szabó, C.; Southan, G. J.; Salzman, A. L. Scavengers of peroxynitrite inhibit the decrease in cellular viability followed by induction of nitric oxide synthase in cultured smooth muscle cells. FASEB J. Abstr. 1995b, A28, 158.
24. Uchida, K.; Kato, Y.; Kawakishi, S. A novel mechanism for oxidative cleavage of prolyl peptides induced by the hydroxyl radical. Biochem. Biophys. Res. Commun. 1990, 169, 265-271.
25. Whiteman, M.; Tritschler, H.; Halliwell, B. Protection against peroxynitrite-dependent tyrosine nitration and α1-proteinase inactivation by oxidized and reduced lipoic acid. FEBS Lett. 1996, 379, 74-76.
26. Wizemann, T. M.; Gardner, C. R.; Laskin, J. D.; Quinones, S.; Durham, S. K.; Goller, N. L.; Ohnishi, S. T.; Laskin, D. L. Production of nitric oxide and peroxynitrite in the lung during acute endotoxemia. J. Leukoc. Biol. 1994, 56, 759-768.
27. Zhu, S.; Haddad, I. Y.; Matalon, S. Nitration of surfactant protein A (SP-A) tyrosine residues results in decreased mannose binding ability. Arch Biochem. Biophys. 1996, 333, 282-290.