EPR spin-trapping of protein radicals to investigate biological oxidative mechanisms

Amino Acids

Volumn 32, Issue 4, 2007, Pages 535-542

  Augusto, O ^a   Muntz Vaz, S ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

EPR; EPR spin trapping; Oxidative mechanisms; Protein radicals

Indexed keywords

CARBONIC ACID DERIVATIVE; FREE RADICAL; OXIDIZING AGENT; PEROXYNITRITE; PROTEIN;

ANALYTIC METHOD; BIOLOGICAL ACTIVITY; CYTOLOGY; CYTOPATHOLOGY; ELECTRON SPIN RESONANCE; HOMEOSTASIS; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN METABOLISM; REVIEW; SIGNAL TRANSDUCTION; TISSUE INJURY;

ANIMALS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HUMANS; OXIDATION-REDUCTION; OXIDATIVE STRESS; PROTEINS; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN SPECIES; SPIN TRAPPING;

EID: 34248528663     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-006-0429-4     Document Type: Review

References (58)

1. Arai H, Berlett BS, Chock PB, Stadtman ER (2005) Effect of bicarbonate on iron-mediated oxidation of low-density lipoprotein. Proc Natl Acad Sci USA 102: 10472-10477
2. Aslund F, Beckwith J (1999) Bridge over troubled waters: sensing stress by dissulfide bond formation. Cell 96: 751-753
3. Augusto O, Bonini MG, Amanso AM, Linares E, Santos CXC, Lopes de Menezes S (2002a) Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology. Free Rad Biol Med 32: 841-859
4. Augusto O, Lopes de Menezes S, Linares E, Romero N, Radi R, Denicola A (2002b) EPR detection of glutathiyl and hemoglobin - cysteinyl radicals during the interaction of peroxynitrite with human erythrocytes. Biochemistry 41: 14323-14328
5. Augusto O, Bonini MG, Trindade DF (2004) Spin trapping of glutathiyl and protein radicals produced from nitric oxide-derived oxidants. Free Rad Biol Med 36: 1224-1232
6. Badouard C, Masuda M, Nishino H, Cadet J, Favier A, Ravanat JL (2005) Detection of chlorinated DNA and RNA nucleosides by HPLC coupled to tandem mass spectrometry as potential biomarkers of inflammation. J Chromatogr B Analyt Technol Biomed Life Sci 827: 26-31
7. Barrows TP, Bhaskar B, Poulos TL (2004) Electrostatic control of the tryptophan radical in cytochrome c peroxidase. Biochemistry 43: 8826-8834
8. Bonini MG, Augusto O (2001) Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite. J Biol Chem 276: 9749-9754
9. Bonini MG, Miyamoto S, Di Mascio P, Augusto O (2004a) Production of the carbonate radical anion during xanthine oxidase turnover in the presence of bicarbonate. J Biol Chem 279: 51836-51843
10. Bonini MG, Fernandes DC, Augusto O (2004b) Albumin oxidation to diverse radicals by the peroxidase activity of Cu,Zn-superoxide dismutase in the presence of bicarbonate or nitrite: diffusible radicals produce cysteinyl and solvent-exposed and -unexposed tyrosyl radicals. Biochemistry 43: 344-351
11. Bryan NS, Rassaf T, Maloney RE, Rodriguez CM, Saijo F, Rodriguez JR, Feelisch M (2004) Cellular targets and mechanisms of nitros(yl)ation: An insight into their nature and kinetics in vivo. Proc Natl Acad Sci USA 101: 4308-4313
12. Carballal S, Radi R, Kirk MC, Barnes S, Freeman BA, Alvarez B (2003) Sulfenic acid formation in human serum albumin by hydrogen peroxide and peroxynitrite. Biochemistry 42: 9906-9914
13. Clairbone AL, Miller H, Parsonage D, Ross PR (1993) Protein-sulfenic acid stabilization and function in enzyme catalysis and gene regulation. FASEB J 7: 1483-1490
14. Dalle-Donne I, Scaloni A, Giustarini D, Cavarra E, Tell G, Lungarella G, Colombo R, Rossi R, Milzani A (2004) Proteins as biomarkers of oxidative/nitrosative stress in diseases: The contribution of redox proteomics. Mass Spectrom Rev 24: 55-99
15. Davies MJ, Hawkins CL (2004) EPR spin-trapping of protein radicals. Free Radic Biol Med 36: 1072-1086
16. Davies MJ, Fu S, Wang H, Dean RT (1999) Stable markers of oxidant damage to proteins and their application in the study of human disease. Free Radic Biol Med 27: 1151-1163
17. Deterding LJ, Ramirez DC, Dubin JR, Mason RP, Tomer KB (2004) Identification of free radicals on hemoglobin from its self-peroxidation using mass spectrometry and immuno-spin trapping: observation of a histidinyl radical. J Biol Chem 279: 11600-11607
18. Elam JS, Malek K, Rodriguez JA, Doucette PA, Taylor AB, Hayward LJ, Cabelli DE, Valentine JS, Hart PJ (2003) An alternative mechanism of bicarbonate-mediated peroxidation by copper-zinc superoxide dismutase: rates enhanced via proposed enzyme-associated peroxycarbonate intermediate. J Biol Chem 278: 21032-21039
19. Espey MG, Thomas DD, Miranda KM, Wink DA (2002) Focusing of nitric oxide mediated nitrosation and oxidative nitrosylation as a consequence of reaction with superoxide. Proc Natl Acad Sci USA 99: 11127-11132
20. Fernandes DC, Medinas DB, Alves MJM, Augusto O (2005) Tempol diverts peroxynitrite/carbon dioxide reactivity toward albumin and cells from protein-tyrosine nitration to protein-cysteine nitrosation. Free Radic Biol Med 38: 189-200
21. Finkel T, Holbrook NJ (2000) Oxidants, oxidative stress and the biology of ageing. Nature 408: 239-247
22. Gatti RM, Radi R, Augusto O (1994) Peroxynitrite-mediated oxidation of albumin to the protein thiyl free radical. FEBS Lett 348: 287-290
23. Georgiou G, Masip L (2003) An overoxidation journey with a return ticket. Science 300: 592-594
24. Gilbert DL, Colton CA (1999) Reactive oxygen species in biological systems: an interdisciplinary approach. Kluwer Academic, New York
25. Halliwell B, Gutteridge JMC (eds) (1999) Free radicals in biology and medicine. Oxford University Press, New York
26. Heo J, Gao G, Campbell SL (2004) pH-dependent perturbation of Ras-guanine nucleotide interactions and Ras guanine nucleotide exchange. Biochemistry 43: 10102-10111
27. Heo J, Prutzman KC, Mocanu V, Campbell SL (2005a) Mechanism of free radical nitric oxide-mediated Ras guanine nucleotide dissociation. J Mol Biol 346: 1423-1440
28. Heo J, Thapar R, Campbell SL (2005b) Recognition and activation of Rho GTPases by Vav1 and Vav2 guanine nucleotide exchange factors. Biochemistry 44: 6573-6585
29. Ignarro LJ (1990) Biosynthesis and metabolism of endothelium-derived nitric oxide. Annu Rev Pharmacol Toxicol 30: 535-560
30. Jourd'heuil D, Jourd'heuil FL, Feelisch M (2003) Oxidation and nitrosation of thiols at low micromolar exposure to nitric oxide. Evidence for a free radical mechanism. J Biol Chem 278: 15720-15726
31. Kadiiska MB, Gladen BC, Baird DD, Germolec D, Graham LB, Parker CE, Nyska A, Wachsman JT, Ames BN, Basu S, Brot N, Fitzgerald GA, Floyd RA, George M, Heinecke JW, Hatch GE, Hensley K, Lawson JA, Marnett LJ, Morrow JD, Murray DM, Plastaras J, Roberts LJ 2nd, Rokach J, Shigenaga MK, Sohal RS, Sun J, Tice RR, Van Thiel DH, Wellner D, Walter PB, Tomer KB, Mason RP, Barrett JC (2005a) Biomarkers of oxidative stress study II: are oxidation products of lipids, proteins, and DNA markers of CCl4 poisoning? Free Radic Biol Med 38: 698-710
32. Kadiiska MB, Gladen BC, Baird DD, Graham LB, Parker CE, Ames BN, Basu S, Fitzgerald GA, Lawson JA, Marnett LJ, Morrow JD, Murray DM, Plastaras J, Roberts LJ 2nd, Rokach J, Shigenaga MK, Sun J, Walter PB, Tomer KB, Barrett JC, Mason RP (2005b) Biomarkers of oxidative stress study III. Effects of the nonsteroidal anti-inflammatory agents indomethacin and meclofenamic acid on measurements of oxidative products of lipids in CCl4 poisoning. Free Radic Biol Med 38: 711-718
33. Knecht KT, Mason RP (1993) In vivo spin-trapping of xenobiotic free radical metabolites. Arch Biochem Biophys 303: 185-194
34. Kris-Etherton PM, Lichtenstein AH, Howard BV, Steinberg D, Witztum JL (Nutrition Committee of the American Heart Association Council on Nutrition, Physical Activity, and Metabolism) (2004) Antioxidant vitamin supplements and cardiovascular disease. Circulation 110: 637-641
35. 2 in cobalt-catalyzed peroxidations. Arch Biochem Biophys 439: 99-104
36. Liochev SI, Fridovich I (2004) Carbon dioxide mediates Mn(II)-catalyzed decomposition of hydrogen peroxide and peroxidation reactions. Proc Natl Acad Sci USA 101: 12485-12490
37. Mason RP (2004) Using anti-5,5-dimethyl-1-pyrroline N-oxide (anti-DMPO) to detect protein radicals in time and space with immuno-spin trapping. Free Radic Biol Med 36: 1214-1223
38. Moncada S, Palmer RM, Higgs EA (1991) Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev 43: 109-142
39. Morrow JD (2005) Quantification of isoprostanes as indices of oxidant stress and the risk of atherosclerosis in humans. Arterioscler Thromb Vasc Biol 25: 279-286
40. Radi R, Denicola A, Alvarez B, Ferrer-Sueta G, Rubbo H (2000) The biological chemistry of peroxynitrite. In: Ignarro LJ (ed) Nitric oxide: biology and pathobiology. Academic Press, New York, pp 57-89
41. Radi R (2004) Nitric oxide, oxidants, and protein tyrosine nitration. Proc Natl Acad Sci USA 101: 4003-4008
42. Ramirez DC, Mejiba SE, Mason RP (2005) Copper-catalyzed protein oxidation and its modulation by carbon dioxide: enhancement of protein radicals in cells. J Biol Chem 280: 27402-27411
43. 2/bicarbonate and hydrogen peroxide. Free Radic Biol Med 35: 1538-1550
44. Richardson DE, Yao H, Frank KM, Bennett DA (2000) Equilibria, kinetics, and mechanisms in the bicarbonate activation of hydrogen peroxide: oxidation of sulfites by peroxymonocarbonate. J Am Chem Soc 122: 1729-1739
45. Romero N, Radi R, Linares E, Augusto O, Detweiler CP, Mason RP, Denicola A (2003) Reaction of human hemoglobin with peroxynitrite: isomerization to nitrate and secondary formation of protein radicals. J Biol Chem 278: 44049-44057
46. Sies H, Mehlhom R (1986) Mutagenicity of nitroxide-free radicals. Arch Biochem Biophys 251: 393-396
47. Shishehbor MH, Aviles RJA, Brennan ML, Fu X, Goormastic M, Pearce GL, Gokce N, Keaney JF, Penn MS, Sprecher DL, Vita JA, Hazen SL (2003) Association of nitrotyrosine levels with cardiovascular disease and modulation by statin therapy. J Am Med Assoc 289: 1675-1680
48. Stamler JS (1994) Redox signaling: nitrosylation and related target interactions of nitric oxide. Cell 78: 931-936
49. Stamler JS (1995) S-Nitrosothiols and the bioregulatory actions of nitrogen oxides through reactions with thiol groups. Curr Top Microbiol Immunol 196: 19-36
50. Stone JR (2004) An assessment of proposed mechanisms for sensing hydrogen peroxide in mammalian systems. Arch Biochem Biophys 422: 119-124
51. Stubbe J, van der Donk W (1998) Protein radicals in enzyme catalysis. Chem Rev 98: 705-762
52. Torres M, Forman HJ (2003) Redox signaling and the MAP kinase pathways. Biofactors 17: 287-296
53. Vasquez-Vivar J, Santos AM, Junqueira VBC, Augusto O (1996) Peroxynitrite-mediated formation of free radicals in human plasma: EPR detection of ascorbyl, albumin-thiyl and uric acid-derived free radicals. Biochem J 314: 869-876
54. Woo HA, Chae HZ, Hwang SC, Yang K-S, Kang SW, Kim K, Rhee SG (2003) Reversing the inactivation of peroxiredoxins caused by cysteine sulfinic acid formation. Science 300: 653-656
55. Wood ZA, Poole LB, Karplus PA (2003) Peroxiredoxin evolution and the regulation of hydrogen peroxide signaling. Science 300: 650-653
56. Yao H, Richardson DE (2003) Bicarbonate surfoxidants: micellar oxidations of aryl sulfides with bicarbonate-activated hydrogen peroxide. J Am Chem Soc 125: 6211-6221
57. Zhang H, Andrekopoulos C, Joseph J, Crow J, Kalyanaraman B (2004) The carbonate radical anion-induced covalent aggregation of human copper, zinc superoxide dismutase, and alpha-synuclein: intermediacy of tryptophan- and tyrosine-derived oxidation. Free Radic Biol Med 36: 1355-1365
58. -: EPR spin trapping studies. J Biol Chem 280: 40684-40698