The Formation and Structure of the Sulfoxyl Radicals RSO·, RSOO·, RSO₂·, and RSO₂OO· from the Reaction of Cysteine, Glutathione and Penicillamine Thiyl Radicals with Molecular Oxygen

References

• Alberti A., Chatgilialoglu C., Guerra M. An investigation of structure and conformation of thiophene-2-sulphonyl radicals. Journal of the Chemical Society, Perkin Transactions II 1986; 1179–1182
   Google Scholar
• Andersen R.S. Electron spin resonance study of x-irradiated single crystals of dimethyl sulfone. Journal of Chemical Physics 1977; 66: 5610–5613
   Web of Science ®Google Scholar
• 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
   Web of Science ®Google Scholar
• Becker D., Yanez J., Sevilla M.D., Alonso-Amigo M.G., Schlick S. An ESR investigation of the motion of lipid peroxyl radicals. Journal of Physical Chemistry 1987; 91: 492–496
   Google Scholar
• Besler B.H., Sevilla M.D., MacNeille P. Ab initio studies of hydrocarbon peroxyl radicals. Journal of Physical Chemistry 1986; 90: 6446–6451
   Web of Science ®Google Scholar
• Boyd R.J., Gupta A., Langler R.F., Lownie S.P., Pincock J.A. Sulfonyl radicals, sulfinic acid and related species: an ab initio molecular orbital study. Canadian Journal of Chemistry 1980; 58: 331–338
   Google Scholar
• Brault D., Neta P., Patterson L.K. The lipid peroxidation model for halogenated hydrocarbon toxicity. Kinetics of peroxyl radical processes involving fatty acids and Fe(III) porphyrins. Chemical-Biological Interactions 1985; 54: 289–297
   PubMed Web of Science ®Google Scholar
• Burton G.W., Ingold K.U. Autoxidation of biological molecules 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. Journal of the American Chemical Society 1981; 103: 6472–6477
   Web of Science ®Google Scholar
• Chatgilialoglu C., Gilbert B.C., Norman R.O.C. Investigations of structure and conformation. Part 14. INDO and electron spin resonance studies of aliphatic sulphonyl radicals. Journal of the Chemical Society, Perkin Transactions II 1980; 1429–1436
   Google Scholar
• Eling T.E., Curtis J.F., Harman L.S., Mason R.P. Oxidation of glutathione to its thiyl free radical metabolite by prostaglandin H synthase. Journal of Biological Chemistry 1986; 261: 5023–5028
   PubMedGoogle Scholar
• Finkel'shtein E.I., Gerasimov G.N. The strength of the RO2 · bond in peroxyl-radicals and the reversibility of the reaction R·+O2⇆RO2·. Russian Journal of Physical Chemistry 1984; 58: 570–572
   Google Scholar
• Gilbert B.C., Kirk C.M., Norman R.O.C., Laue H.A.H. Electron spin resonance studies. Part 51. Aliphatic and aromatic sulphinyl radicals. Journal of the Chemical Society, Perkin Transactions II 1977; 497–501
   Google Scholar
• Gilbert B.C., Laue H.A.H., Norman R.O.C., Sealy R.C. Electron spin resonance studies. Part XLVI. Oxidation of thiols and disulphides in aqueous solution: formation of RS·, RSO·, RSO2·, and RSSR·- and carbon radicals. Journal of the Chemical Society, Perkin Transactions II 1974; 892–900
   Google Scholar
• Harman L.S., Carver D.K., Schreiber J., Mason R.P. One and two-electron oxidation of reduced glutathione by peroxidases. Journal of Biological Chemistry 1986; 261: 1642–1648
   PubMed Web of Science ®Google Scholar
• Harman L.S., Mottley C., Mason R.P. Free radical metabolites of L-cysteine oxidation. Journal of Biological Chemistry 1984; 259: 5606–5611
   PubMed Web of Science ®Google Scholar
• Held K.D., Harrop H.A., Michael B.D. Effects of oxygen and sulfhydrylcontaining compounds on irradiated transforming DNA II. Glutathione, cysteine and cysteamine. International Journal of Radiation Biology 1984; 45: 615–626
   Web of Science ®Google Scholar
• Horowitz A., Rajbenbach L.A. The free radical mechanism of the decomposition of alkylsulfonyl chlorides in liquid cyclohexane. Journal of the American Chemical Society 1975; 97: 10–13
   Google Scholar
• Huie R.E., Neta P. Chemical behavior of SO3- and SO5- radicals in aqueous solutions. Journal of Physical Chemistry 1984; 88: 5665–5669
   Google Scholar
• Ito O., Matsuda M. Chemical kinetics of reactions of sulfur-containing organo radicals. Chemical Kinetics of Small Organo Radicals, Vol. III: Reactions of Special Radicals, Z.B. Alfassi. CRC Press, Boca Raton, Florida 1988; 154–159
   Google Scholar
• Jayson G.G., Stirling D.A., Swallow A.J. Pulse- and x-radiolysis of 2-mercaptoethanol in aqueous solution. International Journal of Radiation Biology 1971; 19: 143–156
   Web of Science ®Google Scholar
• Kevan L., Schlick S. Peroxy spin probes as motional probes in polymers and on oxide surfaces. Journal of Physical Chemistry 1986; 90: 1998–2007
   Google Scholar
• Lal M. Co-60 γ radiolysis of reduced glutathione in aerated solutions at pH values between 1–7·0. Canadian Journal of Chemistry 1976; 54: 1092–1097
   Web of Science ®Google Scholar
• Lal M., Schöneich C., Mönig J., Asmus K.-D. Rate constants for the reactions of halogenated organic radicals. International Journal of Radiation Biology 1988; 54: 773–785
   PubMed Web of Science ®Google Scholar
• Lefebvre R., Maruani J. Use of computer programs in the interpretation of electron paramagnetic resonance spectra of dilute radicals in amorphous samples. I. High-field treatment. X-band spectra of π-electron unconjugated hydrocarbon radicals. Journal of Chemical Physics 1965; 42: 1480–1496
   Web of Science ®Google Scholar
• Mönig J., Asmus K.-D., Forni L.G., Willson R. On the reaction of molecular oxygen with thiyl radicals: a re-examination. International Journal of Radiation Biology 1987; 52: 589–602
   Web of Science ®Google Scholar
• Mottley C., Mason R.P. Sulfate anion free radical formation by the peroxidation of (Bi) sulfite and its reaction with hydroxyl radicals scavengers. Archives of Biochemistry and Biophysics 1988; 267: 681–689
   PubMed Web of Science ®Google Scholar
• Nakamura M., Yamazaki I., Ohtaki S., Nakamura S. Characterization of one and two-electron oxidations of glutathione coupled with Lactoperoxidase and thyroid peroxidase reactions. Journal of Biological Chemistry 1986; 261: 13923–13927
   PubMedGoogle Scholar
• Neta P., Ross A.B. Representative rate constants for radical reactions of biologically important molecules. Chemical Kinetics of Small Organo Radicals, Vol. IV: Reactions in Special Systems, Z.B. Alfassi. CRC Press, Boca Raton, Florida 1988
   Google Scholar
• 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
   Web of Science ®Google Scholar
• Quintiliani M. The oxygen effect in radiation inactivation of DNA and enzymes. International Journal of Radiation Biology 1986; 50: 573–594
   Web of Science ®Google Scholar
• Quintiliani M., Badiello R., Tamba M., Esfandi A., Gorin G. Radiolysis of glutathione in oxygen-containing solutions of pH 7. International Journal of Radiation Biology 1977; 32: 195–202
   Web of Science ®Google Scholar
• Schäfer K., Bonifacic M., Bahnemann D., Asmus K.-D. Addition of oxygen to organic sulfur radicals. Journal of Physical Chemistry 1978; 82: 2777–2780
   Web of Science ®Google Scholar
• Sevilla M.D. Radicals formed by electron attachment to amino acids in an alkaline glass. Journal of Physical Chemistry 1970; 74: 2096–2102
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Becker D., Swarts S., Herrington J. Sulfinyl radical formation from the reaction of cysteine and glutathione thiyl radicals with molecular oxygen. Biochemical and Biophysical Research Communications 1987; 144: 1037–1042
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Yan M., Becker D. Thiol peroxyl radical formation from the reaction of cysteine thiyl radical with molecular oxygen: an ESR investigation. Biochemical and Biophysical Research Communications 1988; 155: 405–410
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Yan M., Becker D., Gillich S. ESR investigations of the reactions of radiation-produced thiyl and DNA peroxyl radicals: formation of sulfoxyl radicals. Free Radical Research Communications 1989; 6: 199–102
   PubMedGoogle Scholar
• Shapiro B., Eldjarn L. The mechanism for the degradation of cystamine by ionizing radiation. Radiation Research 1955; 3: 393–399
   PubMedGoogle Scholar
• Small R.D., Scaiano J.C., Patterson L.K. Radical processes in lipids. A laser photolysis study of t-butoxy radical reactivity toward fatty acids. Photochemistry and Photobiology 1979; 29: 49–51
   Web of Science ®Google Scholar
• Suryanarayana D., Sevilla M.D. INDO study of the anion radicals of acetic acid and acetamide. Nonplanarity and barriers to methyl group rotation. Journal of Physical Chemistry 1980; 84: 3045–3049
   Google Scholar
• Swarts S.G., Becker D., DeBolt S., Sevilla M.D. An electron spin investigation of the structure and formation of sulfinyl radicals: reactions of peroxyl radicals with thiols. Journal of Physical Chemistry 1989; 93: 155–161
   Google Scholar
• Tamba M., Simone G., Quintiliani M. Interactions of thiyl free radicals with oxygen: a pulse radiolysis study. International Journal of Radiation Biology 1986; 50: 595–600
   Web of Science ®Google Scholar
• Thoi H.H., Iino M., Matsuda M. Studies of sulfonyl radicals 5. Activation energies for the decomposition of alkanesulfonyl radicals. Macromolecules 1979; 12: 338–339
   Google Scholar
• von Sonntag C. The Chemical Basis of Radiation Biology. Taylor & Francis, London 1987; 298–298, (a) 345–360; (b) p. 367.
   Google Scholar
• Wardman P. Conjugation and oxidation of glutathione via thiyl free radicals. Glutathione Conjugation: Mechanisms and Biological Significance, H. Sies, B. Ketterer. Academic Press, London 1988; 43–72
   Google Scholar
• Wertz J.E., Bolton J.R. Electron Spin Resonance, Theory and Practical Applications. McGraw-Hill, New York 1972; 171–171
   Google Scholar
• Yanez J., Sevilla C.L., Becker D., Sevilla M.D. Low temperature autoxidation of unsaturated lipids: An electron spin resonance study. Journal of Physical Chemistry 1987; 91: 487–491
   Google Scholar