Slowing of peroxynitrite decomposition in the presence of mannitol and ethanol

Free Radical Biology and Medicine

Volumn 24, Issue 7-8, 1998, Pages 1331-1337

  Alvarez, Beatriz ^a,b   Ferrer Sueta, Gerardo ^b   Radi, Rafael ^a  

^a DEPARTAMENTO DE BIOQUÍMICA   (Uruguay)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

Ethanol; Free radicals; Hydroxyl radical; Mannitol; Nitric oxide; Peroxynitrite; Superoxide

Indexed keywords

ALCOHOL; CYSTEINE; FREE RADICAL; HYDROXYL RADICAL; MANNITOL; NITRIC OXIDE; PEROXYNITRITE; SUPEROXIDE;

ARTICLE; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); DECOMPOSITION; DISSOCIATION; EQUILIBRIUM CONSTANT; HYDROGEN BOND; OXIDATION REDUCTION REACTION; PH; PRIORITY JOURNAL; SPECTROPHOTOMETRY;

BUFFERS; ETHANOL; FREE RADICAL SCAVENGERS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; KINETICS; MANNITOL; MODELS, CHEMICAL; NITRATES; OXIDANTS; SPECTROPHOTOMETRY, ULTRAVIOLET;

LETHRINIDAE;

EID: 17144433859     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(98)00005-7     Document Type: Article

References (44)

1. Radi R., Beckman J. S., Bush K. M., Freeman B. A. Peroxynitrite oxidation of sulfhydryls The cytotoxic potential of superoxide and nitric oxide . J. Biol. Chem. 266:1991;4244-4250.
2. Pryor W. A., Jin X., Squadrito G. L. One- and two-electron oxidations of methionine by peroxynitrite. Proc. Natl. Acad. Sci. USA. 91:1994;11173-11177.
3. Bartlett K., Church D. F., Bounds P. L., Koppenol W. H. The kinetics of the oxidation of L-ascorbic acid by peroxynitrite. Free Radic. Biol. Med. 18:1995;85-92.
4. King P. A., Anderson V. E., Edwards J. O., Gustafson G., Plumb R. C., Suggs J. W. A stable solid that generates hydroxyl radical upon dissolution in aqueous solutions reaction with protein and nucleic acid . J. Am. Chem. Soc. 114:1992;5430-5432.
5. Radi R., Beckman J. S., Bush K. M., Freeman B. A. Peroxynitrite-induced membrane lipid peroxidation the cytotoxic potential of superoxide and nitric oxide . Arch. Biochem. Biophys. 288:1991;481-487.
6. Halfpenny E., Robinson P. L. The nitration and hydroxylation of aromatic compounds by pernitrous acid. J. Chem. Soc. 00:1952;939-946.
7. Ischiropoulos H., Zhu L., Tsai M., Martin J. C., Smith C. D., Beckman J. S. Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 298:1992;431-437.
8. Beckman J. S., Ischiropoulos H., Zhu L., van der Woerd M., Smith C., Chen J., Harrison J., Martin J. C., Tsai M. Kinetics of superoxide dismutase- and iron-catalyzed nitration of phenolics by peroxynitrite. Arch. Biochem. Biophys. 298:1992;438-445.
9. Alvarez B., Rubbo H., Kirk M., Barnes S., Freeman B. A., Radi R. Peroxynitrite-dependent tryptophan nitration. Chem. Res. Toxicol. 9:1996;390-396.
10. Ischiropoulos H., Zhu L., Beckman J. S. Peroxynitrite formation from macrophage-derived nitric oxide. Arch. Biochem. Biophys. 298:1992;446-451.
11. 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 detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler. 375:1994;81-88.
12. Castro L., Rodríguez M., Radi R. Aconitase is readily inactivated by peroxynitrite, but not by its precursor, nitric oxide. J. Biol. Chem. 269:1994;29409-29415.
13. MacMillan-Crow L. A., Crow J. P., Kerby J. D., Beckman J. S., Thompson J. A. Nitration and inactivation of manganese superoxide dismutase in chronic rejection of human renal allografts. Proc. Natl. Acad. Sci. USA. 93:1997;11853-11858.
14. Koppenol W. H., Moreno J. J., Pryor W. A., Ischiropoulos H., Beckman J. S. Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide. Chem. Res. Toxicol. 5:1992;834-842.
15. Augusto O., Gatti R. M., Radi R. Spin-trapping studies of peroxynitrite decomposition and of 3-morpholynosydnonimine N-etylcarbamide autooxidation direct evidence for metal-independent formation of free radical intermediates . Arch. Bioch. Biophys. 310:1994;118-125.
16. Beckman J. S., Beckman T. W., Chen J., Marshall P. A., Freeman B. A. Apparent hydroxyl radical production by peroxynitrite implications for endothelial injury from nitric oxide and superoxide . Proc. Natl. Acad. Sci. USA. 87:1990;1620-1624.
17. Crow J. P., Spruell C., Chen J., Gunn C., Ischiropoulos H., Tsai M., Smith C. D., Radi R., Koppenol W. H., Beckman J. S. On the pH-dependent yield of hydroxyl radical products from peroxynitrite. Free Radic. Biol. Med. 16:1994;331-338.
18. 2-adduct. Chem. Res. Toxicol. 10:1997;1216-1220.
19. -) with its stability. J. Am. Chem. Society. 116:1994;4115-4116.
20. Kissner R., Nauser T., Bugnon P., Lye P. G., Koppenol W. H. Formation and properties of peroxynitrite as studied by laser flash photolysis, high pressure stopped flow and pulse radiolysis. Chem. Res. Toxicol. 10:1997;1285-1292.
21. Pryor W. A., Jin X., Squadrito G. L. Insensitivity of the rate of decomposition of peroxynitrite to changes in viscosity, evidence against free radical formation. J. Am. Chem. Soc. 118:1996;3125-3128.
22. Pryor W. A., Squadrito G. L. The chemistry of peroxynitrite a product from the reaction of nitric oxide with superoxide . Am. J. Physiol. 268:1995;L699-L722.
23. Gatti R. M., Alvarez B., Vasquez-Vivar J., Radi R., Augusto O. Formation of spin trap adducts during the decomposition of peroxynitrite. Arch. Biochem. Biophys. 349:1998;36-46.
24. 2 adduct density functional theory transition structures and energetics . J. Am. Chem. Soc. 118:1996;13002-13006.
25. •OH . Free Radic. Biol. Med. 3:1987;33-39.
26. Ross, A. B.; Bielski, B. H. J.; Buxton, G. V.; Cabelli, D. E.; Greenstock, C. L.; Helman, W. P.; Huie, R. E.; Neta, P. NIST Standard Reference Database 40. NDRL/NIST Solution Kinetic Database. Distributed by National Institute of Standards and Technology (NIST) Standard Reference Data, Gaithersburg, MD, USA; 1992.
27. Gillbe C. E., Sage F. J., Gutteridge J. M. C. Mannitol molecule magnifique or a case of radical misinterpretation? Free Rad. Res. 24:1996;1-7.
28. Alvarez B., Denicola A., Radi R. Reaction between peroxynitrite and hydrogen peroxide formation of oxygen and apparent slowing of peroxynitrite decomposition . Chem. Res. Toxicol. 8:1995;859-869.
29. Goldstein S., Czapski G. Direct and indirect oxidations by peroxynitrite. Inorg. Chem. 34:1995;4041-4048.
30. van der Vliet A., Eiserich J. P., Halliwell B., Cross C. E. Tyrosine modification by reactive nitrogen species a closer look . Arch. Biochem. Biophys. 319:1995;341-349.
31. Ramezanian M. S., Padmaja S., Koppenol W. H. Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chem. Res. Toxicol. 9:1996;160-169.
32. Castro L., Alvarez M. N., Radi R. Modulatory role of nitric oxide on superoxide-dependent luminol chemiluminiscence. Arch. Biochem. Biophys. 333:1996;179-188.
33. Koppenol W. H., Kissner R., Beckman J. S. Synthesis of peroxynitrite to go with the flow or on solid grounds? Packer L. Methods in Enzymology. Vol. 269:1996;296-302 Academic Press, San Diego.
34. Hughes M. N., Hicklin H. G. The chemistry of pernitrites. Part I. Kinetics of decomposition of pernitrous acid. J. Chem. Soc. A. 00:1968;450-456.
35. Quijano C., Alvarez B., Gatti R. M., Augusto O., Radi R. On the pathways of peroxynitrite oxidation of sulfhydryls. Biochem. J. 322:1997;167-173.
36. Halfpenny E., Robinson P. L. The reaction between hydrogen peroxide and nitrous acid, and the properties of an intermediate product. J. Chem. Soc. 00:1952;928-938.
37. Lymar S. V., Hurst J. K. Rapid reaction between peroxynitrite ion and carbon dioxide implications for biological activity . J. Am. Chem. Soc. 117:1995;8867-8868.
38. Pryor W. A., Lemercier J.-N., Zhang H., Uppu R., Squadrito G. L. The catalytic role of carbon dioxide in the decomposition of peroxynitrite. Free Radic. Biol. Med. 23:1997;331-338.
39. Zhang H., Squadrito G. L., Uppu R. M., Lemercier J.-N., Cueto R., Pryor W. A. Inhibition of peroxynitrite-mediated oxidation of glutathione by carbon dioxide. Arch. Biochem. Biophys. 339:1997;183-189.
40. Keith W. G., Powell R. E. Kinetics of decomposition of peroxynitrous acid. J. Chem. Soc. A. 00:1997;90.
41. Tsai, M. A theoretical and experimental study of the conformation of peroxynitrite anion and its high stability, Ph.D. Thesis, University of Alabama at Birmingham, Birmingham, AL, USA; 1994.
42. Tanatar S. Double compounds of hydrogen peroxide with organic substances. J. Russ. Phys. Chem. Soc. 40:1909;376-380.
43. Goldstein S., Squadrito G. L., Pryor W. A., Czapski G. Direct and indirect oxidations by peroxynitrite neither involving hydroxyl radical. Free Radic. Biol. Med. 21:1996;965-974.
44. Radi R. Kinetic analysis of reactivity of peroxynitrite with biomolecules. Packer L. Methods in Enzymology. Vol. 269:1996;354-366 Academic Press, San Diego.