The carbonate radical and related oxidants derived from bicarbonate buffer

IUBMB Life

Volumn 59, Issue 4-5, 2007, Pages 255-262

  Medinas, Danilo B ^a   Cerchiaro, Giselle ^a,b   Trindade, Daniel F ^a   Augusto, Ohara ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSIDADE FEDERAL DO ABC   (Brazil)

Author keywords

Bicarbonate buffer; Carbonate radical; Oxidants

Indexed keywords

BICARBONATE; CARBONIC ACID; COPPER ZINC SUPEROXIDE DISMUTASE; ENZYME; OXIDIZING AGENT; PEROXYMONOCARBONATE; PEROXYNITRITE; SUPEROXIDE DISMUTASE 1 PEROXIDASE; UNCLASSIFIED DRUG; XANTHINE OXIDASE;

AMYOTROPHIC LATERAL SCLEROSIS; BIOCHEMISTRY; CHEMICAL REACTION; CONFERENCE PAPER; ENZYME ACTIVITY; GENE MUTATION; HUMAN; MOTOR NEURON DISEASE; NITRATION; OXIDATION; OXIDATIVE STRESS; PATHOGENESIS; PATHOPHYSIOLOGY; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION;

BICARBONATES; BUFFERS; CARBONATES; FREE RADICALS; MOLECULAR STRUCTURE; OXIDANTS; PEROXYNITROUS ACID; SUPEROXIDE DISMUTASE; XANTHINE OXIDASE;

EID: 34248577756     PISSN: 15216543     EISSN: 15216551     Source Type: Journal    
DOI: 10.1080/15216540701230511     Document Type: Conference Paper

References (55)

1. Finkel, T., and Holbrook, N. J. (2000) Oxidants, oxidative stress and the biology of ageing. Nature 408, 239-247.
2. Torres, M., and Forman, H. J. (2003) Redox signaling and the MAP kinase pathways. Biofactors 17, 287-296.
3. Stone, J. R. (2004) An assessment of proposed mechanisms for sensing hydrogen peroxide in mammalian systems. Arch. Biochem. Biophys. 422, 119-124.
4. Radi, R. (2004) Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl. Acad. Sci. USA 101, 4003-4008.
5. Jones, D. P. (2006) Extracellular redox state: refining the definition of oxidative stress in aging. Rejuvenation Res. 9, 169-181.
6. Augusto, O., and Vaz, S. M. (2007) EPR spin-trapping of protein radical to investigate biological oxidative mechanisms. Amino Acids in press (DOI 10.1007/S00726-006-0429-4).
7. Hodgson, E. K., and Fridovich, I. (1976) The mechanism of the activity-dependent luminescence of xanthine oxidase. Arch. Biochem. Biophys. 172, 202-205.
8. Nakano, M., and Sugioka, K. (1977) Mechanism of chemiluminescence from the linoleate-lipoxygenase system. Arch. Biochem. Biophys. 181, 371-383.
9. Michelson, A. M., and Durosay, P. (1977) Hemolysis of human erythrocytes by activated oxygen species. Photochem. Photobiol. 25, 55-63.
10. Berlett, B. S., Chock, P. B., Yim, M. B., and Stadtman, E. R. (1990) Manganese(II) catalyzes the bicarbonate-dependent oxidation of amino acids by hydrogen peroxide and the amino acid-facilitated dismutation of hydrogen peroxide. Proc. Natl. Acad. Sci. USA 87, 389-393.
11. Sankarapandi, S., and Zweier, J. L. (1999) Bicarbonate is required for the peroxidase function of Cu,Zn-superoxide dismutase at physiological pH. J. Biol. Chem. 274, 1226-1232.
12. Zhang, H., Joseph, J., Felix, C., and Kalyanaraman, B. (2000) Bicarbonate enhances the hydroxylation, nitration, and peroxidation reactions catalyzed by copper, zinc superoxide dismutase. Intermediacy of carbonate anion radical. J. Biol. Chem. 275, 14038-14045.
13. Santos, C. X. C., Bonini, M. G., and Augusto, O. (2000) Role of the carbonate radical in tyrosine nitration and hydroxylation by peroxynitrite. Arch. Biochem. Biophys. 377, 147-152.
14. Bonini, M. G., and 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.
15. 2. J. Biol. Chem. 277, 34674-34678.
16. Zhang, H., Andrekopoulos, C., Joseph, J., Chandran, K., Karoui, H., Crow, J. P., and Kalyanaraman, B. (2003) Bicarbonate-dependent peroxidase activity of human Cu,Zn-superoxide dismutase induces covalent aggregation of protein: intermediacy of tryptophan-derived oxidation products. J. Biol. Chem. 278, 24078-24089.
17. 2. Proc. Natl. Acad. Sci. USA 101, 743-744.
18. Bonini, M. G., Fernandes, D. C., and Augusto O. (2004) 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 42, 344-351.
19. Liochev, S. I., and Fridovich, I. (2004) Carbon dioxide mediates Mn(II)-catalyzed decomposition of hydrogen peroxide and peroxidation reactions. Proc. Natl. Acad. Sci. USA 101, 12485-12490.
20. Ramirez, D. C., Mejiba, S. E., and Mason, R. P. (2005) Coppercatalyzed protein oxidation and its modulation by carbon dioxide: enhancement of protein radicals in cells. J. Biol. Chem. 280, 27402-27411.
21. Arai, H., Berlett, B. S., Chock, P. B., and Stadtman, E. R. (2005) Effect of bicarbonate on iron-mediated oxidation of low-density lipoprotein. Proc. Natl. Acad. Sci. USA 102, 10472-10477.
22. Stadtman, E. R., Arai, H., and Berlett, B. S. (2005) Protein oxidation by the cytochrome P450 mixed-function oxidation system. Biochem. Biophys. Res. Commun. 338, 432-436.
23. 2 in cobalt-catalyzed peroxidations. Arch. Biochem. Biophys. 439, 99-104.
24. Flemmig, J., and Arnhold, J. (2007) Ferrous ion-induced strand breaks in the DNA plasmid pBR322 are not mediated by hydrogen peroxide. Eur. J. Biophys. in press (DOI 10.1007/s00249-006-0093-3).
25. Gotz, R., Gnann, A., and Zimmermann, F. K. (1999) Deletion of the carbonic anhydrase-like gene NCE103 of the yeast Saccharomyces cerevisiae causes an oxygen-sensitive growth defect. Yeast 15, 855-864.
26. Raisanen, S. R., Lehenkari, P., Tasanen, M., Rahkila, P., Harkonen, P. L., and Vaananen, H. K. (1999) Carbonic anhydrase III protects cells from hydrogen peroxide-induced apoptosis. FASEB J. 13, 513-522.
27. Zimmerman U. J., Wang, P., Zhang, X., Bogdanovich, S., and Forster, R. (2004) Anti-oxidative response of carbonic anhydrase III in skeletal muscle. IUBMB Life 56, 343-347.
28. Alvarez-Martinez, C. E., Baldini, R. L., and Gomes, S. L. (2006) A caulobacter crescentus extracytoplasmic function sigma factor mediating the response to oxidative stress in stationary phase. J. Bacteriol. 188, 1835-1846.
29. Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., and Freeman, B. A. (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. USA 87, 1620-1624.
30. Lymar, S. V., and Hurst, J. K. (1995) Rapid reaction between peroxynitrite ion and carbon-dioxide. Implications for biological activity. J. Am. Chem. Soc. 117, 8867-8868.
31. Augusto, O., Bonini, M. G., Amanso, A. M., Linares, E., Santos, C. C., and Lopes de Menezes, S. (2002) Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology. Free Radic. Biol. Med. 32, 841-859.
32. Bonini, M. G., Radi, R., Ferrer-Sueta, G., Ferreira, A. M., and Augusto, O. (1999) Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide. J. Biol. Chem. 274, 10802-10806.
33. Bonini, M. G., Miyamoto, S., Di Mascio, P., and Augusto, O. (2004) Production of the carbonate radical anion during xanthine oxidase turnover in the presence of bicarbonate. J. Biol. Chem. 279, 51836-51843.
34. Czapski, G., Lymar, S. V., and Schwarz, H. A. (1999) Acidity of the carbonate radical. J. Phys. Chem. 103, 3447-3450.
35. Wrona, M., Patel, K., and Wardman, P. (2005) Reactivity of 2′,7′-dichlorodihydrofluorescein and dihydrorhodamine 123 and their oxidized forms toward carbonate, nitrogen dioxide, and hydroxyl radicals. Free Radic. Biol. Med. 38, 262-270.
36. Goldstein, S., Samuni, A., Hideg, K., and Merenyi, G. (2006) Structure-activity relationship of cyclic nitroxides as SOD mimics and scavengers of nitrogen dioxide and carbonate radicals. J. Phys. Chem. A 110, 3679-3685.
37. Domazou, A. S., and Koppenol, W. H. (2007) Oxidation-statedependent reactions of cytochrome c with the trioxidocarbonate(*1-) radical: a pulse radiolysis study. J. Biol. Inorg. Chem. 12, 118-125.
38. Lancaster, J. R. Jr. (2006) Nitroxidative, nitrosative, and nitrative stress: kinetic predictions of reactive nitrogen species chemistry under biological conditions. Chem. Res. Toxicol. 19, 1160-1174.
39. Valentine, J. S., Doucette, P. A., and Potter, S. Z. (2005) Copper-zinc superoxide dismutase and amyotrophic lateral sclerosis. Annu. Rev. Biochem. 74, 563-593.
40. Hodgson, E. K., and Fridovich, I. (1975) The interaction of bovine erythrocyte superoxide dismutase with hydrogen peroxide: inactivation of the enzyme. Biochemistry 14, 5294-5299.
41. Hodgson, E. K., and Fridovich, I. (1975) The interaction of bovine erythrocyte superoxide dismutase with hydrogen peroxide: chemiluminescence and peroxidation. Biochemistry 14, 5299-5303.
42. Yim, M. B., Chock, P. B., and Stadtman, E. R. (1990) Copper, zinc superoxide dismutase catalyzes hydroxyl radical production from hydrogen peroxide. Proc. Natl. Acad. Sci. USA 87, 5006-5010.
43. Elam, J. S., Malek, K., Rodriguez, J. A., Doucette, P. A., Taylor, A. B., Hayward, L. J., Cabelli, D. E., Valentine, J. S., and Hart, P. J. (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.
44. Millar, T. M., Kanczler, J. M., Bodamyali, T., Blake, D. R., and Stevens, C. R. (2002) Xanthine oxidase is a peroxynitrite synthase: newly identified roles for a very old enzyme. Redox Rep. 7, 65-70.
45. Harrison, R. (2002) Structure and function of xanthine oxidoreductase: where are we now? Free Radic. Biol. Med. 33, 774-797.
46. Flanagan, J., Jones, D. P., Griffith, W. P., Skapski, A. C., and West, A. P. (1986) On the existence of peroxocarbonates in aqueous solution. J. Chem. Soc. Chem. Commun. 1, 20-21.
47. Richardson, D. E., Yao, H., Frank, K. M., and Bennett, D. A. (2000) Equilibria, kinetics, and mechanism in the bicarbonate activation of hydrogen peroxide: oxidation of sulfides by peroxymonocarbonate. J. Am. Chem. Soc. 122, 1729-1739.
48. Bennett, D. A., Yao, H., and Richardson, D. E. (2001) Mechanism of sulfide oxidations by peroxymonocarbonate. Inorg. Chem. 40, 2996-3001.
49. 2/bicarbonate and hydrogen peroxide. Free Radic. Biol. Med. 35, 1538-1550.
50. Trindade, D. F., Cerchiaro, G., and Augusto, O. (2006) A role for peroxymonocarbonate in the stimulation of biothiol peroxidation by the bicarbonate/carbon dioxide pair. Chem. Res. Toxicol. 19, 1475-1482.
51. Wong, P. K., Poyer, J. L., DuBose, C. M., and Floyd, R. A. (1988) Hydralazine-dependent carbon dioxide free radical formation by metabolizing mitochondria. J. Biol. Chem. 263, 11296-11301.
52. 4 in the perfused rat liver and in vivo. J. Biol. Chem. 261, 4542-4548.
53. Vasquez-Vivar, J., Denicola, A., Radi, R., and Augusto, O. (1997) Peroxynitrite-mediated decarboxylation of pyruvate to both carbon dioxide and carbon dioxide radical anion. Chem. Res. Toxicol. 10, 786-794.
54. Xiao, C., Palmer, D. A., Wesolowski D. J., Lovitz, S. B., and King, W. D. (2002) Carbon dioxide effects on luminol and 1,10-phenatroline chemiluminescence. Anal. Chem. 74, 2210-2216.
55. Wadhawan, J. D., Welford, P. J., Maisonhaute, E., Climent, V., Lawrence, N. S., McPeak, H. B., Hahn, C. E. W., and Compton, R. G. (2001) Microelectrode studies of the reaction of superoxide with carbon dioxide in dimethyl sulfoxide. J. Phys. Chem. B, 105, 10659-10668.