91
Views
3
CrossRef citations to date
0
Altmetric
Original Article

Electrons initiate efficient formation of hydroperoxides from cysteine

Pages 987-996 | Received 10 May 2016, Accepted 08 Jul 2016, Published online: 08 Aug 2016

References

  • Gebicki S, Gebicki JM. Formation of peroxides in amino acids and proteins exposed to oxygen free radicals. Biochem J 1993;289:743–749.
  • Gebicki JM. Protein hydroperoxides as new reactive oxygen species. Redox Rep 1997;3:99–110.
  • Davies MJ, Dean RT. Radical-mediated protein oxidation. Oxford: Oxford University Press; 1997:1–443.
  • Hawkins CL, Davies MJ. EPR studies on the selectivity of hydroxyl radical attack on amino acids and peptides. J Chem Soc Perkin Trans 2 1998:2617–2622.
  • Gebicki JM. The role of proteins in biological damage induced by oxidative stress. In: Pietzsch J, ed. Protein oxidation and disease. Trivandrum: Research Signpost; 2006:7–38.
  • Gebicki JM. Oxidative stress, free radicals and protein peroxides. Arch Biochem Biophys 2016;595:33–39.
  • Davies MJ. Protein oxidation and peroxidation. Biochem J 2016;473:805–825.
  • Gieseg S, Duggan S, Gebicki JM. Peroxidation of proteins before lipids in U937 cells exposed to peroxyl radicals. Biochem J 2000;350:215–218.
  • Fu S, Davies MJ, Stocker R, Dean RT. Evidence for roles of radicals in protein oxidation in advanced human athrerosclerotic plaques. Biochem J 1998;333:519–525.
  • Abramovitch S, Rabani J. Pulse radiolytic investigations of peroxy radicals in aqueous solutions of acetate and glycine. J Phys Chem 1976;80:1562–1565.
  • Von Sonntag C. The chemical basis of radiation biology. London: Taylor and Francis, Inc; 1987.
  • Caldwell KA, Tappel AL. Reactions of seleno- and sulfoamino acids with hydroperoxides. Biochemistry 1964;3:1643–1647.
  • Gebicki S, Gill KH, Dean RT, Gebicki JM. Action of peroxidases on protein hydroperoxides. Redox Rep 2002;7:235–242.
  • Zhao R, Lind J, Merenyi G, Eriksen TE. Kinetics of one-electron oxidation of thiols and hydrogen abstraction by thiyl radicals from a-amino C-H bonds. J Am Chem Soc 1994;116:12010–12015.
  • Nauser T, Koppenol WH, Schöneich C. Reversible hydrogen transfer reactions in thiyl radicals from cysteine and related molecules: absolute kinetics and equilibrium constants determined by pulse radiolysis. J Phys Chem B 2012;116:5329–5341.
  • Bielski BHJ, Gebicki JM. Application of radiation chemistry to biology. In: Pryor WA, ed. Free radicals in biology. Vol III. New York (NY): Academic Press; 1977:1–51.
  • O’Donnel JH, Sangster DF. Principles of radiation chemistry. London: Edward Arnold; 1970.
  • Hicks M, Gebicki JM. A spectrophotometric method for the determination of lipid hydroperoxides. Anal Biochem 1979;99:249–253.
  • Jessup W, Dean RT, Gebicki JM. Iodometric determination of hydroperoxides in lipids and proteins. Meth Enzymol 1994;233:289–303.
  • Ellman GL. Tissue sulfhydryl groups. Arch Biochem Biophys 1959;82:70–77.
  • Flohe L, Gunzler WA. Assays of glutathione peroxidase. Meth Enzymol 1984;105:114–121.
  • Wilkening VG, Lal M, Arends M, Armstrong DA. The cobalt-60 gamma radiolysis of cysteine in deaerated aqueous solutions at pH values between 5 and 6. J Phys Chem 1968;72:185–190.
  • Lal M. 60Co-gamma radiolysis of cysteine in aeratedd solutions at pH 5.5–6.0. Radiat Effects 1974;22:237–242.
  • Buxton G, Greenstock C, Helman W, Ross A. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (OHbul/O-bul) in aqueous solution. J Phys Chem Ref Data 1988;17:513–886.
  • Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J Phys Chem Ref Data 1989;18:1637–1755.
  • Koppenol WH, Butler J. Energetics of interconversion reactions of oxyradicals. Adv Free Rad Biol Med 1985;1:91–131.
  • Oxygen solubility in fresh and sea water. Available from: www.EngineeringToolBox.com
  • Sjoberg L, Eriksen TE, Revesz L. The reaction of the hydroxyl radical with glutathione in neutral and alkaline aqueous solution. Radiat Res 1982;89:255–263.
  • Eriksen T, Fransson G. Formation of reducing radicals on radiolysis of glutathione and some related compounds in aqueous solution. J Chem Soc Perkin Trans II 1988:1117–1122.
  • Grierson L, Hildenbrand K, Bothe E. Intramolecular transformation reaction of the glutathione thiyl radical into a non-sulphur-centred radical: a pulse-radiolysis and EPR study. Int J Radiat Biol 1992;62:265–277.
  • Zhao R, Lind J, Merenyi G, Eriksen T. Significance of the intramolecular transformation of glutathione thyil radicals to alpha-aminoalkyl radicals. Thermochemical and biological implications. J Chem Soc Perkin Trans 2 1997:569–574.
  • Hofstetter D, Nauser T, Koppenol WH. Hydrogen exchange equilibria in glutathione radicals: rate constants. Chem Res Toxicol 2010;23:1596–1600.
  • Al-Thannon A, Barton J, Packer J, Sims R, Trumbore C, Winchester R. The radiolysis of aqueous solutions of cysteine in the presence of oxygen. Int J Radiat Phys Chem 1974;6:233–247.
  • Barton JP, Packer JE. Radiolysis of oxygenated cysteine solutions at neutral pH. The role of RSSR and O2-. Int J Radiat Phys Chem 1970;2:159–166.
  • Sevilla MD, Becker D, Yan M. 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. Int J Radiat Biol 1990;57:65–81.
  • Sevilla MD, Yan MY, Becker D. Thiol peroxyl radical formation from the reaction of cysteine thiyl radical with molecular oxygen: an ESR investigation. Biochem Biophys Res Commun 1988;155:405–410.
  • Tamba M, Simone G, Quintiliani M. Interactions of thiyl free radicals with oxygen: a pulse radiolysis study. Int J Radiat Biol Relat Stud Phys Chem Med 1986;50:595–600.
  • Schäfer K, Bonifacic M, Bahnemann D, Asmus K-D. Addition of oxygen to organic sulfur radicals. J Phys Chem 1978;82:2777–2780.
  • Mönig J, Asmus KD, Forni LG, Willson RL. On the reaction of molecular oxygen with thiyl radicals: a re-examination. Int J Radiat Biol Relat Stud Phys Chem Med 1987;52:589–602.
  • Hoffman MZ, Hayon E. Pulse radiolysis study of sulfhydryl compounds in aqueous solution. J Phys Chem 1973;77:990–996.
  • Navon G, Stein G. The reactivity of atomic hydrogen with cysteine, cystine, tryptophan and tyrosine in aqueous solution. Isr J Chem 1964;2:151–154.
  • Mageli OL, Sheppard CS. Organic peroxides and peroxy compound – general description. In: Swern D, ed. Organic peroxides. Vol. 1. New York: John Wiley & Sons Inc; 1970:1–104.
  • Wardman P, von Sonntag C. Kinetic factors that control the fate of thiyl radicals in cells. Meth Enzymol 1995;251:31–45.
  • Schöneich C, Mozziconacci O, Koppenol WH, Nauser T. Intramolecular 1,2- and 1,3-hydrogen transfer reactions of thiyl radicals. Isr J Chem 2014;54:265–271.
  • Winterbourn CC. Reconciling the chemistry and biology of reactive oxygen species. Nat Chem Biol 2008;4:278–286.
  • Winterbourn CC. Are free radicals involved in thiol-based redox signaling? Free Radic Biol Med 2015;80:164–170.
  • Schöneich C. Mechanisms of protein damage induced by cysteine thiyl radical formation. Chem Res Toxicol 2008;21:1175–1179.
  • Nauser T, Pelling J, Schöneich C. Thiyl radical reaction with amino acid side chains: rate constants for hydrogen transfer and relevance for posttranslational protein modification. Chem Res Toxicol 2004;17:1323–1328.

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.