pH profile of cytochrome c-catalyzed tyrosine nitration

Acta Biochimica Polonica

Volumn 53, Issue 3, 2006, Pages 577-584

  Kambayashi, Yasuhiro ^a   Hitomi, Yoshiaki ^a   Kodama, Norio ^a,c   Kubo, Masayuki ^a,d   Okuda, Junna ^a   Takemoto, Kei ^a,b   Shibamori, Masafumi ^a,c   Takigawa, Tomoko ^b   Ogino, Keiki ^a,b  

^a KANAZAWA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c OTSUKA PHARMACEUTICAL CO LTD   (Japan)

^d YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

Cytochrome c; Nitrite; Nitrotyrosine; pH; Pseudo peroxidase

Indexed keywords

EID: 33749835014     PISSN: 0001527X     EISSN: 1734154X     Source Type: Journal    
DOI: 10.18388/abp.2006_3330     Document Type: Article

References (50)

1. Abu-Soud HM, Hazen SL (2000) Nitric oxide modulates the catalytic activity of myeloperoxidase. J Biol Chem 275: 5425-5430.
2. Alonso D, Encinas JM, Uttenthal LO, Boscá L, Serrano J, Fernández AP, Castro-Blanco S, Santacana M, Bentura ML, Richart A, Fernández-Vizarra P, Rodrigo J (2002) Coexistence of translocated cytochrome c and nitrated protein in neurons of the rat cerebral cortex after oxygen and glucose deprivation. Neurosci 111: 47-56.
3. Anbar M, Taube H (1954) Interaction of nitrous acid with hydrogen peroxide and with water. J Am Chem Soc 76: 6243-6247.
4. Barr DP, Gunther MR, Deterding LJ, Tomer KB, Mason RP (1996) ESR spin-trapping of a protein-derived tyrosyl radical from the reaction of cytochrome c with hydrogen peroxide. J Biol Chem 271: 15498-15503.
5. Batthyány C, Souza JM, Durán R, Cassina A, Cerveñansky C, Radi R (2005) Time course and site(s) of cytochrome c tyrosine nitration by peroxynitrite. Biochemistry 44: 8038-8046.
6. Bian K, Gao Z, Weisbrodt N, Murad F (2003) The nature of heme/iron-induced protein tyrosine nitration. Proc Natl Acad Sci USA 100: 5712-5717.
7. Blough NV, Zafiriou OC (1985) Reaction of superoxide with nitric oxide to form peroxynitrite in alkaline aqueous solution. Inorg Chem 24: 3502-3504.
8. Boveris A, Cadenas E (1975) Mitochondrial production of superoxide anions ands its relationship to the antimycin insensitive respiration. FEBS Lett 54: 311-314.
9. Butt WD, Keilin D (1962) Absorption spectra and some other properties of cytochrome c and of its compounds with ligands. Proc Biol Sci/R Soc 156: 429-458.
10. Cassina AM, Hodara R, Souza JM, Thomson L, Castro L, Ischiropoulos H, Freeman BA, Radi R (2000) Cytochrome c nitration by peroxynitrite. J Biol Chem 275: 21409-21415.
11. Castro L, Eiserich JP, Sweeney S, Radi R, Freeman BA (2004) Cytochrome c: a catalyst and target of nitrite-hydrogen peroxide-dependent protein nitration. Arch Biochem Biophys 421: 99-107.
12. Chen YR, Chen CL, Chen W, Zweier JL, Augusto O, Radi R, Mason RP (2004) Formation of protein tyrosine ortho-semiquinone radical and nitrotyrosine from cytochrome c-derived tyrosyl radical. J Biol Chem 279: 18054-18062.
13. de Jongh HHJ, Ritsema T, Killian JA (1995) Lipid specificity for membrane mediated partial unfolding of cytochrome c. FEBS Lett 360: 255-260.
14. Deterding LJ, Barr DP, Mason RP, Tomer KB (1998) Characterization of cytochrome c free radical reactions with peptides by mass spectrometry. J Biol Chem 273: 12863-12869.
15. Forman JH, Kennedy J (1975) Superoxide production and electron transport in mitochondrial oxidation of dihydroorotic acid. J Biol Chem 250: 4322-4326.
16. Furtmüller PG, Burner U, Regelsberger G, Obinger C (2000) Spectral and kinetic studies on the formation of eosinophil peroxidase compound I and its reaction with halides and thiocyanate. Biochemistry 39: 15578-15584.
17. Gȩbicka L, Didik J (2003) Mechanism of peroxynitrite interaction with cytochrome c. Acta Biochim Polon 50: 815-823.
18. Gȩbicka L, Didik J (2005) Does the peroxidase-like activity of sodium dodecyl sulphate-modified cytochrome c increase after peroxynitrite or radiation treatment? Acta Biochim Polon 52: 551-555.
19. Ghafourifar P, Richter C (1997) Nitric oxide synthase activity in mitochondria. FEBS Lett 418: 291-296.
20. Ghafourifar P, Schenk U, Klein SD, Richter C (1999) Mitochondrial nitric-oxide synthase stimulation causes cytochrome c release from isolated mitochondria. Evidence for intramitochondrial peroxynitrite formation. J Biol Chem 274: 31185-31188.
21. Ghafourifar P, Cadenas E (2005) Mitochondrial nitric oxide synthase. Trends Pharmacol Sci 26: 190-195.
22. Giulivi C, Poderoso JJ, Boveris A (1998) Production of nitric oxide by mitochondria. J Biol Chem 273: 11038-11043.
23. Greenacre SAB, Ischiropoulos H (2001) Tyrosine nitration: localization, quantification, consequences for protein function and signal transduction. Free Radic Res 34: 541-581.
24. Grzelak A, Balcerczyk A, Mateja A, Bartosz G (2001) Hemoglobin can nitrate itself and other proteins. Biochim Biophys Acta 1528: 97-100.
25. Herold S (2004) Nitrotyrosine, dityrosine, and nitrotryptophan formation from metmyoglobin, hydrogen peroxide, and nitrite. Free Radic Biol Med 36: 565-579.
26. Hortelano S, Alvarez AM, Boscá L (1999) Nitric oxide induces tyrosine nitration and release of cytochrome c preceding an increase of mitochondrial transmembrane potential in macrophages. FASEB J 13: 2311-2317.
27. Ischiropoulos H, Zhu L, Chen J, Tsai M, Martin JC, Smith CD, Beckman JS (1992) Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch Biochem Biophys 298: 431-437.
28. Jang B, Han S (2006) Biochemical properties of cytochrome c nitrated by peroxynitrite. Biochimie 88: 53-58.
29. Jiang J, Serinkan BF, Tyurina YY, Borisenko GG, Mi Z, Robbins PD, Schroit AJ, Kagan VE (2003) Peroxidation and externalization of phosphatidylserine associated with release of cytochrome c from mitochondria. Free Radic Biol Med 35: 814-825.
30. Kagan VE, Gleiss B, Tyurina YY, Tyurin VA, Elenstrom-Magnusson C, Liu SX, Serinkan FB, Arroyo A, Chandra J, Orrenius S, Fadeel B (2002) A role for oxidative stress in apoptosis: oxidation and externalization of phosphatidylserine is required for macrophage clearance of cells undergoing Fas-mediated apoptosis. J Immunol 169: 487-499.
31. Kilinc K, Kilinc A, Wolf RE, Grisham MB (2001) Myoglobin-catalyzed tyrosine nitration: no need for peroxynitrite. Biochem Biophys Res Commun 285: 273-276.
32. Kluck RM, Bossy-Wetzel E, Green DR, Newmeyer DD (1997) The release of cytochrome c from mitochondria: a primary site for Bcl-2 regulation of apoptosis. Science 275: 1132-1136.
33. 2. Implications for oxidative stress during apoptosis. J Biol Chem 278: 29410-29419.
34. Liu X, Kim CN, Yang J, Jemmerson R, Wang X (1996) Induction of apoptotic program in cell-free extracts: requirement for dATP and cytochrome c. Cell 86: 147-157.
35. Marquez LA, Huang JT, Dunford HB (1994) Spectral and kinetic studies on the formation of myeloperoxidase compounds I and II: roles of hydrogen peroxide and superoxide. Biochemistry 33: 1447-1454.
36. 2 solutions in the UV). Anal Biochem 49: 474-478.
37. Nomura K, Imai H, Koumura T, Kobayashi T, Nakagawa Y (2000) Mitochondrial phospholipid hydropeoxide glutathione peroxidase inhibits the release of cytochrome c from mitochondria by suppressing the peroxidation of cardiolipin in hypoglycaemia-induced apoptosis. Biochem J 351: 183-193.
38. Ogino K, Kodama N, Nakajima M, Yamada A, Nakamura H, Nagase H, Sadamitsu D, Maekawa T (2001) Catalase catalyzes nitrotyrosine formation from sodium azide and hydrogen peroxide. Free Radic Res 35: 735-747.
39. Ogino K, Nakajima M, Kodama N, Kubo M, Kimura S, Nagase H, Nakamura H (2002) Immunohistochemical artifact for nitrotyrosine in eosinophils or eosinophil containing tissue. Free Radic Res 36: 1163-1170.
40. Orii Y, Shimada H (1978) Reaction of cytochrome c with nitrite and nitric oxide. A model of dissimilatory nitrite reductase. J Biochem 84: 1542-1552.
41. Petrosillo G, Ruggiero FM, Paradies G (2003) Role of reactive oxygen species and cardiolipin in the release of cytochrome c from mitochondria. FASEB J 17: 2202-2208.
42. Qian SY, Chen YR, Deterding LJ, Fann YC, Chignell CF, Tomer KB, Mason RP (2002) Identification of protein-derived tyrosyl radical in the reaction of cytochrome c and hydrogen peroxide: characterization by ESR spin-trapping, HPLC and MS. Biochem J 363: 281-288.
43. Radi R, Thomson L, Rubbo H, Prodanov E (1991) Cytochrome c-catalyzed oxidation of organic molecules by hydrogen peroxide. Arch Biochem Biophys 288: 112-117.
44. Ricoux R, Boucher JL, Mansuy D, Mahy JP (2001) Microperoxidase 8 catalyzed nitration of phenol by nitrogen dioxide radicals. Eur J Biochem 268: 3783-3788.
45. Sampson JB, Ye Y, Rosen H, Beckman JS (1998) Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch Biochem Biophys 356: 207-213.
46. x-induced nitration: assay for 3-nitrotyrosine by HPLC with electrochemical detection. Proc Natl Acad Sci USA 94: 3211-3216.
47. Stellwagen E (1968) Carboxymethylation of horse heart ferricytochrome c and cyanferricytochrome c. Biochemistry 7: 2496-2501.
48. Totsune H, Ohno C, Kambayashi Y, Nakano M, Ushijima Y, Tero-Kubota S, Ikegami Y (1999) Characteristics of chemilumescence observed in the horseradish peroxidase-hydrgen peroxide-tyrosine system. Arch Biochem Biophys 369: 233-242.
49. van der Vliet A, Eiserich JP, Halliwell B, Cross CE (1997) Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide-dependent toxicity. J Biol Chem 272: 7617-7625.
50. Wu W, Chen Y, Hazen SL (1999) Eosinophil peroxidase nitrates protein tyrosyl residues. Implications for oxidative damage by nitrating intermediates in eosinophilic inflammatory disorders. J Biol Chem 274: 25933-25944.