34
Views
9
CrossRef citations to date
0
Altmetric
Research Article

Interaction of tert -butyl Hydroperoxide with Hypochlorous Acid. A Spin Trapping and Chemiluminescence Study

, , &
Pages 749-754 | Published online: 07 Jul 2009

  • Thomas, E.L. (1979) "Myeloperoxidase, hydrogen peroxide, chloride antimicrobial system: nitrogen-chloride derivatives of bacterial components in their action against Escherichia coli", Infect. Immun. 25, 110-116.
  • Albrich, J.M., McCarthy, M.C. and Hurst, J.K. (1981) "Biological reactivity of hypochlorous acid: implication for microbicidal mechanism of leukocyte myeloperoxidase", Proc. Natl. Acad. USA 78, 210-214.
  • Tsan, M.F. (1982) "Myeloperoxidase-mediated oxidation of methionine", J. Cell Physiol. Ill, 49-54.
  • Winterbourn, C.C. (1985) "Comparative reactivities of various biological compounds with myeloperoxidase-hydrogen peroxide-chloride, and similarity of the oxidant to hypochlorite", Biochim. Biophys. Acta 840, 204-210.
  • Arnhold, J., Hammerschmidt, S. and Arnold, K. (1991) "Role of functional groups of human plasma and luminol in scavenging of NaOCl and neutrophil-derived hypochlorous acid", Biochim. Biophys. Acta 1097, 145-151.
  • Weiss, S.J., Lampert, M.B. and Test, S.T. (1982) "Long-lived oxidants generated by human neutrophils: characterization and bioactivity", Science 222, 625-628.
  • Grisham, M.B., Jefferson, M.M., Melton, D.J. and Thomas, E.L. (1984) "Chlorination of endogenous amines by isolated neutrophils", J. Biol. Chem. 259, 10404-10412.
  • Klebanoff, S.J. (1988) "Phagocytic cells: Products of oxygen metabolism", In: Gallin, J.I., Goldstein, I.M. and Snyderman, R., eds, Inflammation. Basic Principles and Clinical Correlates (Raven Press, New York), pp 391-443.
  • Sepe, S.M. and Clark, R.A. (1985) "Oxidant membrane injury by the neutrophil myeloperoxidase system. I. Characterization of a liposome model and injury by myeloperoxidase, hydrogen peroxide, and halides", J. IImmunol. 134, 1888-1895.
  • Stelmaszynska, T, Kukovetz, E., Egger, G. and Schaur, R.J. (1992) "Possible involvement of myeloperoxidase in lipid peroxidation", Int. J. Biochem. 24, 121-128.
  • Panasenko, O.M., Arnhold, J., Schiller, J., Arnold, K. and Sergienko, V.I. (1994) "Peroxidation of egg yolk phosphatidylcholine liposomes by hypochlorous acid", Biochim. Biophys. Acta 1215, 259-266.
  • Panasenko, O.M., Evgina, S.A., Aidyraliev, R.K., Sergienko, V.I. and Vladimirov, Yu.A. (1994) "Peroxidation of human blood lipoproteins induced by exogenous hypochlorite or hypochlorite generated in the system of myeloperoxidase + H2O2 + Cl", Free Radie. Biol. Med. 16, 143-148.
  • Panasenko, O.M., Evgina, S.A., Driomina, E.S., Sharov, VS., Sergienko, VI. and Vladimirov, Yu.A. (1995) "Hypochlorite induces lipid peroxidation in blood lipoproteins and phospolipid liposomes", Free Radie. Biol. Med. 19, 133-140.
  • Panasenko, O.M. and Arnhold, J. (1996) "Mechanisms of hypochlorite-induced peroxidation in phospholipid liposomes", Membr. Cell Biol. 10, 93-104.
  • Panasenko, O.M., Arnhold, J., Vladimirov, Y.A., Arnold, K. and Sergienko, VI. (1997) "Hypochlorite-induced peroxidation of egg yolk phosphatidylcholine is mediated by hydroperoxides", Free Radie. Res. 27, 1-12.
  • Panasenko, O.M. and Arnhold, J. (1999) "Linoleic acid hydroperoxide favours hypochlorite- and myeloperoxidaseinduced lipid peroxidation", Free Radie. Res. 30, 479-487.
  • Khan, A.U. and Kasha, M. (1970) "Chemiluminescence arising from simultaneous transitions in pairs of singlet oxygen molecules", J. Am. Chem. Soc. 92, 3293-3300.
  • Held, A.M., Halko, D.J. and Hurst, J.K. (1978) "Mechanisms of chlorine oxidation of hydrogen peroxide", J. Am. Chem. Soc. 100, 5732-5740.
  • Panasenko, D.M., Arnhold, J. and Schiller, J. (1997) "Hypochlorite reacts with an organic hydroperoxide forming free radicals, but not singlet oxygen, and thus initiates lipid peroxidation", Biochemistry (Mosc.) 62, 951-959.
  • Arnhold, J., Panasenko, O.M., Schiller, J., Arnold, K., Vladimirov, YA. and Sergienko, V.I. (1996) "Reaction of hypochlorous acid with hydrogen peroxide and ferf-butyl hydroperoxide. 1H-NMR spectroscopy and chemiluminescence analyses", Z. Naturforsch. Sic, 386-394.
  • Morris, J.C. (1966) "The acid ionization constant of HOCl from 5 to 35°", . Phys. Chem. 195, 133-140.
  • Duling, D.R. (1994) "Simulation of multiple isotropic spintrap EPR spectra", J. Magn. Reson., Ser. B 104, 105-110.
  • Rodriguez, L.O. and Hecht, S.M. (1982) "Iron (Ill)-bleomycin. Biochemical and spectral properties in the presence of radical scavengers", Biochem. Biophys. Res. Commun. 104, 1470-1476.
  • Mottley, C., Connor, H.D. and Mason, R.P. (1986) "[17O]UXygen hyperfine structure for the hydroxyl radical and Superoxide radical adducts of the spin traps DMPO, PBN and 4-POBN", Biochem. Biophys. Res. Commun. 141, 622-628.
  • Schaich, K.M. and Borg, D.C. (1980) "ESR studies in autoxidation", In: Simic, M.G. and Karel, M., eds, Autoxidation in food and biological systems (Plenum Press, New York), pp 45-70.
  • Osipov, A.N., Savov, V.M., Yak'hyaev, A.V., Zubarev, V.E., Azizova, O.A., Kagan, VE. and Vladimirov, YA. (1984) "Spintrapping study of radicals generated in the reaction of organic peroxides with ferrous ion", Bioflzika 29, 533-536.
  • Osipov, A.N., Moravsky, A.P., Shuvalov, VF., Azizova, O.A. and Vladimirov, YA. (1980) "Study of destruction of peroxide radicals in lipids", Bioflzika 25, 234-238.
  • Osipov, A.N., Zubarev, VE., Azizova, O.A. and Vladimirov, YA. (1980) "Identification of adducts of hydroxyl and water radicals with a spin trap using C-phenyl-N-tert-butylnitrone", Zh. flzicheskoj chimii 54, 3067-3070.
  • Gunther, M.R., Hanna, P.M., Mason, R.P. and Cohen, M.S. (1995) "Hydroxyl radical formation from cuprous ion and hydrogen peroxide: A spin trapping study", Arch. Biochem. Biophys. 316, 515-522.
  • Russell, G.A. (1957) "Deuterium-isotope effects in the autoxidation of aralkyl hydrocarbons. Mechanism of the interaction of peroxy radicals", J. Am. Chem. Soc. 79, 3871-3877.
  • Howard, J.A. and Ingold, K.U. (1968) "The self-reaction of sec-butylperoxy radicals. Confirmation of the Russell mechanism", J. Am. Chem. Soc. 90, 1056-1058.
  • Koppenol, W.H. (1994) "Thermodynamic considerations on the formation of reactive species from hypochlorite, superoxide and nitrogen monoxide. Could nitrosyl chloride be produced by neutrophils and macrophages?", FEBS Lett. 347, 5-8.
  • Koppenol, W.H. (1990) "Oxyradical reactions: from bonddissociation energies to reduction potentials", FEBS Lett. 264, 165-167.
  • Jovanovic, S.V., Jankovic, I. and Josimovic, L. (1992) "Electron-transfer reactions of alkyl peroxy radicals", J. Am. Chem. Soc. 114, 9018-9021.
  • Howard, J.A. and Tait, J.C. (1978) "Electron paramagnetic resonance spectra of the fert-butylperoxy and iert-butoxy adducts to phenyl fert-butyl nitrone and 2-methyl-2-nitrosopropane. Oxygen-17 hyperfine splitting constants", Can. J. Chem. 56, 176-178.
  • Janzen, E.G., Krygsman, PH., Lindsay, D.A. and Haire, D.L. (1990) "Detection of alkyl, alkoxyl, and alkylperoxyl radicals from the thermolysis of azobis(isobutyronitrile) by ESR/spin trapping. Evidence for double spin adducts from liquidphase chromatography and mass spectroscopy", J. Am. Chem. Soc. 112, 8279-8284.
  • Dikalov, S.I. and Mason, R.P. (1999) "Reassignment of organic peroxyl radical adducts", Free Radie. Biol. Med. 27, 864-872.
  • Dikalov, S.I. and Mason, R.P. (2001) "Spin trapping of polyunsaturated fatty acid-derived peroxyl radicals: reassignment to alkoxyl radical adducts", Free Radie. Biol. Med. 30, 187-197.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.