Incorporation of the hydrophobic probe N-t-BOC-L-tyrosine tert-butyl ester to red blood cell membranes to study peroxynitrite-dependent reactions

Chemical Research in Toxicology

Volumn 20, Issue 11, 2007, Pages 1638-1648

  Romero, Natalia ^a   Peluffo, Gonzalo ^a   Bartesaghi, Silvina ^a,b   Zhang, Hao ^c   Joseph, Joy ^c   Kalyanaraman, Balaraman ^c   Radi, Rafael ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b DEPARTAMENTO DE BIOQUÍMICA   (Uruguay)

^c FREE RADICAL RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; CARBON DIOXIDE; FREE RADICAL; N TERT BUTOXYCARBONYL L TYROSINE TERT BUTYL ESTER; NITRATE; OXYHEMOGLOBIN; PEROXYNITRITE; SCAVENGER RECEPTOR; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIMERIZATION; ERYTHROCYTE MEMBRANE; HYDROPHOBICITY; ISOMERIZATION; MEMBRANE PERMEABILITY; NITRATION; TYROSINE NITRATION;

CARBON DIOXIDE; DIMERIZATION; ERYTHROCYTE MEMBRANE; FREE RADICALS; HUMANS; HYDROPHOBICITY; NITROGEN; OXIDATION-REDUCTION; OXYHEMOGLOBINS; PEROXYNITROUS ACID; TYROSINE;

EID: 37249045163     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700142a     Document Type: Article

References (61)

1. Brito, C., Naviliat, M., Tiscornia, A. C., Vuillier, F., Gualco, G., Dighiero, G., Radi, R., and Cayota, A. M. (1999) Peroxynitrite inhibits T lymphocyte activation and proliferation by promoting impairment of tyrosine phosphorylation and peroxynitrite- driven apoptotic death. J. Immunol. 162, 3356-3366.
2. Szabo, C. (2006) Poly(ADP-ribose) polymerase activation by reactive nitrogen species - Relevance for the pathogenesis of inflammation. Nitric Oxide 14, 169-179.
3. Estevez, A. G., Spear, N., Manuel, S. M., Radi, R., Henderson, C. E., Barbeito, L., and Beckman, J. S. (1998) Nitric oxide and superoxide contribute to motor neuron apoptosis induced by trophic factor deprivation. J. Neurosci. 18, 923-931.
4. Ischiropoulos, H., and Beckman, J. S. (2003) Oxidative stress and nitration in neurodegeneration: Cause, effect, or association? J. Clin. Invest. 111, 163-169.
5. Sarchielli, P., Galli, F., Floridi, A., and Gallai, V. (2003) Relevance of protein nitration in brain injury: A key pathophysiological mechanism in neurodegenerative, autoimmune, or inflammatory CNS diseases and stroke. Amino Acids 25, 427-436.
6. Guzik, T. J., West, N. E., Pillai, R., Taggart, D. P., and Channon, K. M. (2002) Nitric oxide modulates superoxide release and peroxynitrite formation in human blood vessels. Hypertension 39, 1088-1094.
7. Turko, I. V., and Murad, F. (2002) Protein nitration in cardiovascular diseases. Pharmacol. Rev. 54, 619-634.
8. Escobales, N., and Crespo, M. J. (2005) Oxidative-nitrosative stress in hypertension. Curr. Vasc. Pharmacol. 3, 231-246.
9. Beckmann, 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 tyrosines in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe Seyler 375, 81-88.
10. Luoma, J. S., Stralin, P., Marklund, S. L., Hiltunen, T. P., Sarkioja, T., and Yla-Herttuala, S. (1998) Expression of extracellular SOD and iNOS in macrophages and smooth muscle cells in human and rabbit atherosclerotic lesions: Colocalization with epitopes characteristic of oxidized LDL and peroxynitrite-modified proteins. Arterioscler., Thromb., Vasc. Biol. 18, 157-167.
11. Cromheeke, K. M., Kockx, M. M., De Meyer, G. R., Bosmans, J. M., Bult, H., Beelaerts, W. J., Vrints, C. J., and Herman, A. G. (1999) Inducible nitric oxide synthase colocalizes with signs of lipid oxidation/peroxidation in human atherosclerotic plaques. Cardiovasc. Res. 43, 744-754.
12. 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, 49-58.
13. Augusto, O., Bonini, M. G., Amanso, A. M., Linares, E., Santos, C. C., and De Menezes, S. L. (2002) Nitrogen dioxide and carbonate radical anion: Two emerging radicals in biology. Free Radical Biol. Med. 32, 841-859.
14. Radi, R., Peluffo, G., Alvarez, M. N., Naviliat, M., and Cayota, A. (2001) Unraveling peroxynitrite formation in biological systems. Free Radical Biol. Med. 30, 463-488.
15. Radi, R. (2004) Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl. Acad. Sci. U.S.A. 101, 4003-4008.
16. Alvarez, B., Ferrer-Sueta, G., Freeman, B. A., and Radi, R. (1999) Kinetics of peroxynitrite reaction with amino acids and human serum albumin. J. Biol. Chem. 274, 842-848.
17. Bartesaghi, S., Ferrer-Sueta, G., Peluffo, G., Valez, V., Zhang, H., Kalyanaraman, B., and Radi, R. (2007) Protein tyrosine nitration in hydrophilic and hydrophobic environments. Amino Acids 32, 501-515.
18. Mallozzi, C., Di Stasi, A. M., and Minetti, M. (1997) Peroxynitrite modulates tyrosine-dependent signal transduction pathway of human erythrocyte band 3. FASEB J. 11, 1281-1290.
19. Velsor, L. W., Ballinger, C. A., Patel, J., and Postlethwait, E. M. (2003) Influence of epithelial lining fluid lipids on NO(2)-induced membrane oxidation and nitration. Free Radical Biol. Med. 34, 720-733.
20. Murray, J., Taylor, S. W., Zhang, B., Ghosh, S. S., and Capaldi, R. A. (2003) Oxidative damage to mitochondrial complex I due to peroxynitrite: Identification of reactive tyrosines by mass spectrometry. J. Biol. Chem. 278, 37223-37230.
21. Xu, S., Ying, J., Jiang, B., Guo, W., Adachi, T., Sharov, V., Lazar, H., Menzoian, J., Knyushko, T. V., Bigelow, D., Schoneich, C., and Cohen, R. A. (2006) Detection of sequence-specific tyrosine nitration of manganese SOD and SERCA in cardiovascular disease and aging. Am. J. Physiol. Heart Circ. Physiol. 290, H2220-H2227.
22. Shao, B., Bergt, C., Fu, X., Green, P., Voss, J. C., Oda, M. N., Oram, J. F., and Heinecke, J. W. (2005) Tyrosine 192 in apolipoprotein A-I is the major site of nitration and chlorination by myeloperoxidase, but only chlorination markedly impairs ABCA1-dependent cholesterol transport. J. Biol. Chem. 280, 5983-5993.
23. Hsiai, T. K., Hwang, J., Barr, M. L., Correa, A., Hamilton, R., Alavi, M., Rouhanizadeh, M., Cadenas, E., and Hazen, S. L. (2007) Hemodynamics influences vascular peroxynitrite formation: Implication for low-density lipoprotein apo-B-100 nitration. Free Radical Biol. Med. 42, 519-529.
24. Zhang, H., Joseph, J., Feix, J., Hogg, N., and Kalyanaraman, B. (2001) Nitration and oxidation of a hydrophobic tyrosine probe by peroxynitrite in membranes: comparison with nitration and oxidation of tyrosine by peroxynitrite in aqueous solution. Biochemistry 40, 7675-7686.
25. Bartesaghi, S., Valez, V., Trujillo, M., Peluffo, G., Romero, N., Zhang, H., Kalyanaraman, B., and Radi, R. (2006) Mechanistic studies of peroxynitrite-mediated tyrosine nitration in membranes using the hydrophobic probe N-t-BOC-L-tyrosine tert-butyl ester. Biochemistry 45, 6813-6825.
26. Zhang, H., Bhargava, K., Keszler, A., Feix, J., Hogg, N., Joseph, J., and Kalyanaraman, B. (2003) Transmembrane nitration of hydrophobic tyrosyl peptides. Localization, characterization, mechanism of nitration, and biological implications. J. Biol. Chem. 278, 8969-8978.
27. -: EPR SPIN trapping studies. J. Biol. Chem. 280, 40684-40698.
28. Romero, N., Denicola, A., Souza, J. M., and Radi, R. (1999) Diffusion of peroxynitrite in the presence of carbon dioxide. Arch. Biochem. Biophys. 368, 23-30.
29. Denicola, A., Souza, J. M., and Radi, R. (1998) Diffusion of peroxynitrite across erythrocyte membranes. Proc. Natl. Acad. Sci. U.S.A. 95, 3566-3571.
30. Romero, N., and Radi, R. (2005) Hemoglobin and red blood cells as tools for studying peroxynitrite biochemistry. Methods Enzymol. 396, 229-245.
31. Romero, N., Radi, R., Linares, E., Augusto, O., Detweiler, C. D., Mason, R. P., and Denicola, A. (2003) Reaction of human hemoglobin with peroxynitrite. Isomerization to nitrate and secondary formation of protein radicals. J. Biol. Chem. 278, 44049-44057.
32. Ferrer-Sueta, G., Quijano, C., Alvarez, B., and Radi, R. (2002) Reactions of manganese porphyrins and manganese-superoxide dismutase with peroxynitrite. Methods Enzymol. 349, 23-37.
33. Kucherenko, Y., Browning, J., Tattersall, A., Ellory, J. C., and Gibson, J. S. (2005) Effect of peroxynitrite on passive K+ transport in human red blood cells. Cell Physiol. Biochem. 15, 271-280.
34. Celedon, G., Gonzalez, G., Pino, J., and Lissi, E. A. (2007) Peroxynitrite oxidizes erythrocyte membrane band 3 protein and diminishes its anion transport capacity. Free Radical Res. 41, 316-323.
35. Soszynski, M., and Bartosz, G. (1996) Effect of peroxynitrite on erythrocytes. Biochim. Biophys. Acta 1291, 107-114.
36. Romero, N., Denicola, A., and Radi, R. (2006) Red blood cells in the metabolism of nitric oxide-derived peroxynitrite. IUBMB Life 58, 572-580.
37. Minetti, M., Pietraforte, D., Carbone, V., Salzano, A. M., Scorza, G., and Marino, G. (2000) Scavenging of peroxynitrite by oxyhemoglobin and identification of modified globin residues. Biochemistry 39, 6689-6697.
38. 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.
39. Steck, T. L., and Kant, J. A. (1974) Preparation of impermeable ghosts and inside-out vesicles from human erythrocyte membranes. Methods Enzymol. 31, 172-180.
40. Bligh, E. G., and Dyer, W. J. (1959) A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37, 911-917.
41. Espenson, J. H. (1995) Chemical Kinetics and Reaction Mechanisms, 2nd ed., McGraw-Hill, New York.
42. Winterbourn, C. C. (1990) Oxidative reactions of hemoglobin. Methods Enzymol. 186, 265-272.
43. Detweiler, C. D., Deterding, L. J., Tomer, K. B., Chignell, C. F., Germolec, D., and Mason, R. P. (2002) Immunological identification of the heart myoglobin radical formed by hydrogen peroxide. Free Radical Biol. Med. 33, 364-369.
44. Tanaka, Y., Mashino, K., Inoue, K., and Nojima, S. (1983) Mechanism of human erythrocyte hemolysis induced by short-chain phosphatidylcholines and lysophosphatidylcholine. J. Biochem. (Tokyo) 94, 833-840.
45. Mashino, K., Tanaka, Y., Takahashi, K., Inoue, K., and Nojima, S. (1983) Hemolytic activities of various phospholipids and their relation to the rate of transfer between membranes. J. Biochem. (Tokyo) 94, 821-831.
46. Spiteller, G. (2006) Peroxyl radicals: Inductors of neurodegenerative and other inflammatory diseases. Their origin and how they transform cholesterol, phospholipids, plasmalogens, polyunsaturated fatty acids, sugars, and proteins into deleterious products. Free Radical Biol. Med. 41, 362-387.
47. Jennings, M. L. (1989) Structure and function of the red blood cell anion transport protein. Annu. Rev. Biophys. Biophys. Chem. 18, 397-430.
48. Lux, S. E., John, K. M., Kopito, R. R., and Lodish, H. F. (1989) Cloning and characterization of band 3, the human erythrocyte anion-exchange protein (AE1). Proc. Natl. Acad. Sci. U.S.A. 86, 9089-9093.
49. Goldstein, S., and Czapski, G. (1995) Direct and indirect oxidations by peroxynitrite. Inorg. Chem. 34, 4041-4048.
50. Pietraforte, D., Matarrese, P., Straface, E., Gambardella, L., Metere, A., Scorza, G., Leto, T. L., Malorni, W., and Minetti, M. (2007) Two different pathways are involved in peroxynitrite-induced senescence and apoptosis of human erythrocytes. Free Radical Biol. Med. 42, 202-214.
51. Tiffert, T., Lew, V. L., Perdomo, D., and Ginsburg, H. (2000) Effect of ferriprotoporphyrin IX and non-heme iron on the Ca(2+) pump of intact human red cells. J. Membr. Biol. 175, 107-113.
52. Omodeo-Sale, F., Motti, A., Dondorp, A., White, N. J., and Taramelli, D. (2005) Destabilisation and subsequent lysis of human erythrocytes induced by Plasmodium falciparum haem products. Eur. J. Haematol. 74, 324-332.
53. Famin, O., Krugliak, M., and Ginsburg, H. (1999) Kinetics of inhibition of glutathione-mediated degradation of ferriprotoporphyrin IX by antimalarial dregs. Biochem. Pharmacol. 58, 59-68.
54. Erben-Russ, M., Bors, W., and Saran, M. (1987) Reactions of linoleic acid peroxyl radicals with phenolic antioxidants: A pulse radiolysis study. Int. J. Radiat. Biol. 52, 393-412.
55. Jacob, J. S., Cistola, D. P., Hsu, F. F., Muzaffar, S., Mueller, D. M., Hazen, S. L., and Heinecke, J. W. (1996) Human phagocytes employ the myeloperoxidase-hydrogen peroxide system to synthesize dityrosine, trityrosine, pulcherosine, and isodityrosine by a tyrosyl radical-dependent pathway. J. Biol. Chem. 271, 19950-19956.
56. Heinecke, J. W., Li, W., Francis, G. A., and Goldstein, J. A. (1993) Tyrosyl radical generated by myeloperoxidase catalyzes the oxidative cross-linking of proteins. J. Clin. Invest. 91, 2866-2872.
57. Cassina, A. M., Hodara, R., Souza, J. M., Thomson, L., Castro, L., Ischiropoulos, H., Freeman, B. A., and Radi, R. (2000) Cytochrome c nitration by peroxynitrite. J. Biol. Chem. 275, 21409-21415.
58. Ostdal, H., Davies, M. J., and Andersen, H. J. (2002) Reaction between protein radicals and other biomolecules. Free Radical Biol. Med. 33, 201-209.
59. Szabo, C., Ischiropoulos, H., and Radi, R. (2007) Peroxynitrite: biochemistry, pathophysiology and development of therapeutics. Nat. Rev. Drug Discovery 6, 662-680.
60. Ye, Y., Quijano, C., Robinson, K. M., Ricart, K. C., Strayer, A. L., Sahawneh, M. A., Shacka, J. J., Kirk, M., Barnes, S., Accavitti-Loper, M. A., Radi, R., Beckman, J. S., and Estevez, A. G. (2007) Prevention of peroxynitrite-induced apoptosis of motor neurons and PC12 cells by tyrosine-containing peptides. J. Biol. Chem. 282, 6324-6337.
61. Goldstein, S., Saha, A., Lymar, S. V., and Czapski, G. (1998) Oxidation of peroxynitrite by inorganic radicals: A pulse radiolysis study. J. Am. Chem. Soc. 120, 5549-5554.