Kinetics of oxidation of tyrosine by a model alkoxyl radical

Free Radical Research

Volumn 46, Issue 9, 2012, Pages 1150-1156

  Folkes, Lisa K ^a   Bartesaghi, Silvina ^b   Trujillo, Madia ^b   Radi, Rafael ^b   Wardman, Peter ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b DEPARTAMENTO DE BIOQUÍMICA   (Uruguay)

Author keywords

Kinetics; Pulse radiolysis; Rate constant; Tert butoxyl; Tyrosyl

Indexed keywords

RADICAL; TERT BUTOXYL RADICAL; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); FRAGMENTATION REACTION; OXIDATION; PH; PULSE RADIOLYSIS; SPECTROPHOTOMETRY;

ALCOHOLS; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, CHEMICAL; OXIDATION-REDUCTION; TYROSINE;

EID: 84864663970     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.3109/10715762.2012.695868     Document Type: Article

References (39)

1. Giulivi C, Traaseth NJ, Davies KJ. Tyrosine oxidation pro- ducts: analysis and biological relevance. Amino Acids 2003;25:227-232. (Pubitemid 38041261)
2. Bartesaghi S, Ferrer-Sueta G, Peluff o G, Valez V, Zhang H, Kalyanaraman B, et al. Protein tyrosine nitration in hydrophilic and hydrophobic environments. Amino Acids 2007;32: 501-515. (Pubitemid 46790931)
3. Radi R. Nitric oxide, oxidants, and protein tyrosine nitration. Proc Natl Acad Sci USA 2004;101:4003-4008. (Pubitemid 38405874)
4. Folkes LK, Trujillo M, Bartesaghi S, Radi R, Wardman P. Kinetics of reduction of tyrosine phenoxyl radicals by glu- tathione. Arch Biochem Biophys 2011;506:242-249.
5. Bartesaghi S, Wenzel J, Trujillo M, Lopez M, Joseph J, Kalyanaraman B, et al. Lipid peroxyl radicals mediate tyrosine dimerization and nitration in membranes. Chem Res Toxicol 2010;23:821-835.
6. Radi R, Turrens JF, Freeman BA. Cytochrome c-catalyzed membrane lipid peroxidation by hydrogen peroxide. Arch BiochemBiophys 1991;288:118-125.
7. Wilcox AL, Marnett LJ. Polyunsaturated fatty acid alkoxyl radicals exist as carbon-centered epoxyallylic radicals: A key step in hydroperoxide-amplifi ed lipid peroxidation. Chem Res Toxicol 1993;6:413-416. (Pubitemid 23212505)
8. Yin H, Xu L, Porter NA. Free radical lipid peroxidation: mech- anisms and analysis. Chem Rev 2011;111:5944-5972.
9. Davies MJ, Fu S, Dean RT. Protein hydroperoxides can give rise to reactive free radicals. Biochem J 1995;305:643-649.
10. Hawkins CL, Davies MJ. Generation and propagation of radical reactions on proteins. Biochim Biophys Acta 2001; 1504:196-219. (Pubitemid 32201893)
11. Van der Zee J. Formation of peroxide-and globin-derived radicals from the reaction of methaemoglobin and metmyoglo- bin with t-butyl hydroperoxide: an ESR spin-trapping investi- gation. Biochem J 1997;322:633-639. (Pubitemid 127737319)
12. M é renyi G, Lind J, Engman L. One-and two-electron reduc- tion potentials of peroxyl radicals and related species. J Chem Soc, Perkin Trans 2 1994;2551-2553.
13. Mer é nyi G, Lind J, Goldstein S. Thermochemical properties of α-hydroxy-alkoxyl radicals in aqueous solution. J Phys Chem A2002;106:11127-11129. (Pubitemid 35433870)
14. Harriman A. Further comments on the redox properties of trytophan and tyrosine. J Phys Chem 1987;91:6102-6104.
15. 3̄ radicals in aqueous solution. J Phys Chem A 1999;103:3581-3588.
16. Erben-Russ M, Michel C, Bors W, Saran M. Absolute rate constants of alkoxyl radical reactions in aqueous solution. J Phys Chem 1987;91:2362-2365.
17. Lymar SV, Schwarz HA. Hydrogen atom reactivity toward aqueous tert-butyl alcohol. J Phys Chem A 2012;116: 1383-1389.
18. Phulkar S, Rao BSM, Schuchmann H-P, von Sonntag C. Radio- lysis of tertiary butyl hydroperoxide in aqueous solution. Reductive cleavage by the solvated electron, the hydrogen atom, and, in particular, the superoxide radical anion. Z Natur- forsch 1990;45b:1425-1432.
19. Ross AB, Mallard WG, Helman WP, Buxton GV, Huie RE, Neta P. NDRL-NIST Solution Kinetics Database: Ver. 3. Notre Dame Radiation Laboratory and National Institute of Stand- ards and Technology. Notre Dame, Indiana and Gaithersburg, Maryland; 1998. http://www.rcdc.nd.edu/.
20. Madej E, Wardman P. The oxidizing power of the glutathione thiyl radical as measured by its electrode potential at physio- logical pH. Arch Biochem Biophys 2007;462:94-102. (Pubitemid 46755135)
21. 2̄ in aqueous solutions. RadiatRes 1976;67:1-8.
22. Land EJ, Ebert M. Pulse radiolysis studies of aqueous phenol. Trans Faraday Soc 1967;63:1181-1190.
23. Gilbert BC, Marshall PDR, Norman ROC, Pineda N, Williams PS. Electron spin resonance studies. Part 61. The generation and reactions of the t-butoxyl radical in aqueous solution. J Chem Soc Perkin Trans 2 1981;1392-1400.
24. Buettner GR. The pecking order of free radicals and antioxi- dants: lipid peroxidation, α-tocopherol, and ascorbate. Arch Biochem Biophys 1993;300:535-543. (Pubitemid 23232908)
25. Das TN, Dhanasekaran T, Alfassi ZB, Neta P. Reduction poten- tial of the tert-butylperoxyl radical in aqueous solutions. J Phys Chem A 1998;102:280-284.
26. Jonsson M. Thermochemical properties of peroxides and peroxyl radicals. J Phys Chem 1996;100:6814-6818. (Pubitemid 126790411)
27. Neta P, Huie RE, Ross AB. Rate constants for reactions of inorganic radicals in aqueous solution. J Phys Chem Ref Data 1988;17:1027-1284.
28. Tratnyek PG, Hoign é J. Kinetics of reactions of chlorine dioxide (OClO) in water-II. Quantitative structure-activity relation- ships for phenolic compounds. Water Res 1994;28:57-66.
29. Napolitano MJ, Green BJ, Nicoson JS, Margerum DW. Chlorine dioxide oxidations of tyrosine, N-acetyltyrosine, and dopa. Chem Res Toxicol 2005;18:501-508. (Pubitemid 40393172)
30. 2 · at basic pH. Radiat Phys Chem 1987;29:405-406. (Pubitemid 17094859)
31. Adams GE, Aldrich JE, Bisby RH, Cundall RB, Redpath JL, Willson RL. Selective free radical reactions with proteins and enzymes: reactions of inorganic radical anions with amino acids. Radiat Res 1972;49:278-289.
32. Cudina I, Jovanovic SV. Free radical inactivation of trypsin. Radiat Phys Chem 1988;32:497-501.
33. 2·) with amino acids: pulse radiolysis evidence. Life Sci 1978;23: 2617-2620. (Pubitemid 9079236)
34. Land EJ, Pr ü tz WA. Reaction of azide radicals with amino acids and proteins. Int J Radiat Biol 1979;36:75-83. (Pubitemid 9244524)
35. Buxton GV. Measurement of rate constants for radical reac- tions in the liquid phase. In: Alfassi ZB (ed.). General aspects of the chemistry of radicals. Chichester: John Wiley & Sons Ltd; 1999. pp. 51-77.
36. Buxton GV, Mulazzani QG. Radiation-chemical techniques. In: Balzani V (ed.). Electron transfer in chemistry. Weinheim: Wiley-VCH; 2001. pp. 503-557.
37. Tsentalovich YP, Kulik LK, Gritsan NP, Yurkovskaya AV. Sol- vent eff ects on the rate of β-scission of the tert-butoxyl radical. J Phys Chem A 1998;102:7975-7980.
38. Weber M, Fischer H. Absolute rate constants for the β-scission and hydrogen abstraction reactions of the tert-butoxyl radical and for several radical rearrangements: evaluating delayed radical formations by time-resolved electron spin resonance. J Am Chem Soc 1999;121:7381-7388.
39. Petralia S, Spatafora C, Tringali C, Foti MC, Sortino S. Hydro- gen atom abstraction from resveratrol and two lipophilic derivatives by tert-butoxyl radicals. A laser fl ash photolysis study. New J Chem 2004;28:1484-1487. (Pubitemid 40070424)