66
Views
64
CrossRef citations to date
0
Altmetric
Original Article

Intramolecular Transformation Reaction of the Glutathione Thiyl Radical into a Non-sulphur-centred Radical: A Pulse-radiolysis and EPR Study

, &
Pages 265-277 | Received 03 Feb 1992, Accepted 14 Apr 1992, Published online: 03 Jul 2009

References

  • Adams G.E. Radiation chemical mechanisms in radiation biology. Advances in Radiation Chemistry 1972; 3: 125–208
  • Adams G.E., Willson R.L. Ketyl radicals in aqueous solution. Pulse radiolysis study. Journal of the Chemical Society, Faraday Transactions 1973; 1: 719–729
  • Adams G.E., McNaughton G.S., Michael B.D. Pulse radiolysis of sulphur compounds. Part 2. Free radical ‘repair’ by hydrogen transfer from sulphydryl compounds. Transactions of the Faraday Society 1968; 64: 902–910
  • Akhlaq M.S., von Sonntag C. Intermolecular H-abstraction of thiyl radicals from thiols and the intramolecular complexing of the thiyl radical with the thiol group in 1,4-dithiothreitol. A pulse radiolysis study. Zeitschift für Naturforschung 1987; 42c: 134–140
  • Akhlaq M.S., Schuchmann H.-P., von Sonntag C. The reverse of the ‘repair’ reaction of thiols: H-abstraction at carbon by thiyl radicals. International Journal of Radiation Biology 1987; 51: 91–102
  • Baker M.Z., Badiello R., Tamba M., Quintiliani M., Goron G. Pulse radiolytic study of hydrogen transfer from glutathione to organic radicals. International Journal of Radiation Biology 1982; 41: 595–602
  • Becker D., Swarts S., Champagne M., Sevilla M.D. An ESR investigation of the reactions of glutathione, cysteine and penicillamine thiyl radicals: competitive formation of RSO·, R·, RSSR·-, and RSS·-. International Journal of Radiation Biology 1988; 53: 767–786
  • Behrens G., Schulte-Frohlinde D. Radikale aus der Oxidation von Essigsäure-2-hydroxyäthylester. Eine in situ-ESR-Studie. Berichte der Bunsengesellschaft für Physikalische Chemie 1976; 80: 429–436
  • Das S., von Sonntag C. The oxidation of trimethylamine by OH radicals in aqueous solution, as studied by pulse radiolysis, ESR, and product analysis. The reactions of the alkylamine radical cation, the aminoalkyl radical, and the protonated aminoalkyl radical. Zeitschift für Naturforschung 1986; 41b: 505–513
  • Eiben K., Fessenden R.W. Electron spin resonance studies of transient radicals in aqueous solutions. Journal of Physical Chemistry 1971; 75: 1186–1201
  • Ellman G.L. Tissue sulphydryl groups. Archives of Biochemistry and Biophysics 1959; 82: 70–77
  • Eriksen T.E., Fransson G. Radical-induced oxidation of glutathione in alkaline aqueous solution. Radiation Physics and Chemistry 1988a; 32: 163–167
  • Eriksen T.E., Fransson G. Formation of reducing radicals on radiolysis of glutathione and some related compounds in aqueous solution. Journal of the Chemical Society, Perkin Transactions 1988b; 2: 1117–1122
  • Felix C.C., Sealy R.C. Electron spin resonance characterization of radicals from 3,4-dihydroxyphenylalanine: semiquinone anions and their metal chelates. Journal of the American Chemical Society 1981; 103: 2831–2836
  • Gilbert B.C., Trenwith M. An investigation into the effects of chirality upon electron spin resonance spectra. Journal of the Chemical Society, Perkin Transactions 1973; 2: 1834–1839
  • Gilbert B.C., Larkin J.P., Norman R.O.C. Electron spin resonance studies. Part XXXIV. The use of the aci-anion from nitromethane as a spin-trap for organic radicals in aqueous solution. Journal of the Chemical Society, Perkin Transactions 1972; 2: 1272–1279
  • Hiller K.-O., Asmus K.-D. Formation and reduction reactions of α-amino radicals derived from methionine and its derivatives in aqueous solutions. Journal of Physical Chemistry 1983; 87: 3682–3688
  • Hoffman M.Z., Hayon E. One-Electron reduction of the disulfide linkage in aqueous solution. Formation, protonation, and decay kinetics of the RSSR- radical. Journal of the American Chemical Society 1972; 94: 7950–7957
  • Hoffman M.Z., Hayon E. Pulse radiolysis study of sulfhydryl compounds in aqueous solution. Journal of Physical Chemistry 1973; 77: 990–996
  • Huckerby T.N., Tudor A.J., Dawber J.G. Acid-Base Studies of glutathione (l-γ-glutamyl-l-cysteinyl-l-glycine) by one- and two-dimensional nuclear magnetic resonance spectroscopy. Journal of the Chemical Society, Perkin Transactions 1985; 2: 759–763
  • Liphard M., Bothe E., Schulte-Frohlinde D. The influence of glutathione on single-strand breakage in single-stranded DNA irradiated in aqueous solution in the absence and presence of oxygen. International Journal of Radiation Biology 1990; 58: 589–602
  • Neta P., Fessenden R.W. Electron spin resonance study of radicals produced in irradiated aqueous solutions of thiols. Journal of Physical Chemistry 1971; 75: 2277–2283
  • Nucifora G., Smaller B., Remko R., Avery E.C. Transient radicals of DNA bases by pulse radiolysis. Effects of cysteine and cysteamine as radioprotectors. Radiation Research 1972; 49: 96–111
  • O'Neill P. Pulse radiolytic study of the interaction of thiols and ascorbate with OH-adducts of dGMP and dG. Implications for DNA repair processes. Radiation Research 1983; 96: 198–210
  • Packer J.E. The radiation chemistry of thiols. The Chemistry of the Thiol Group, S. Patai. Wiley, London 1974; 481–517, In Part 2.
  • Prütz W.A., Butler J., Land E.J., Swallow A.J. The role of sulphur peptide functions in free radical transfer: a pulse radiolysis study. International Journal of Radiation Biology 1989; 55: 539–556
  • Prütz W.A., Mönig H. On the effect of oxygen or copper(II) in radiation-induced degradation of DNA in the presence of thiols. International Journal of Radiation Biology 1987; 52: 677–682
  • Schöneich C., Asmus K.-D. Reaction of thiyl radicals with alcohols, ethers and polyunsaturated fatty acids: a possible role of thiyl free radicals in thiol mutagenesis?. Radiation and Environmental Biophysics 1990; 29: 263–271
  • Schöneich C., Bonifacic M., Asmus K.-D. Reversible H-atom abstraction from alcohols by thiyl radicals: determination of absolute rate constants by pulse radiolysis. Free Radical Research Communications 1989; 6: 393–405
  • Schuler R.H., Hartzell A.L., Behar B. Track effects in radiation chemistry. Concentration dependence for the scavenging of OH by ferrocyanide in N2O-saturated solutions. Journal of Physical Chemistry 1981; 85: 192–199
  • Sevilla M.D., D'Arcy J.B., Morehouse K.M. An electron spin resonance study of γ-irradiated frozen aqueous solutions containing dipeptides. Mechanisms of radical reaction. Journal of Physical Chemistry 1979; 83: 2887–2892
  • Sjöberg L., Eriksen T.E., Revesz L. The reaction of the hydroxyl radical with glutathione in neutral and alkaline aqueous solution. Radiation Research 1982; 89: 255–263
  • Tomkiewicz M., McAlpine R.D., Cocivera M. Photoxidation and decarboxylation of tyrosine studied by e.p.r. and c.i.d.n.p. techniques. Canadian Journal of Chemistry 1972; 50: 3849–3856
  • von Sonntag C. The Chemical Basis of Radiation Biology. Taylor & Francis, London 1987; 353–374
  • von Sonntag C., Schuchmann H.-P. Radiation chemistry of thiols, sulphides and disulphides. The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Sulphur Analogues, S. Patai. Wiley, Chichester 1980; 971–993, In Part 2. The Chemistry of Functional Groups, Suppl. E

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.