Kinetics and mechanism of the reaction of a nitroxide radical (tempol) with a phenolic antioxidant

Free Radical Research

Volumn 37, Issue 3, 2003, Pages 225-230

  Aliaga, C ^a   Lissi, E A ^b   Augusto, O ^c   Linares, E ^c  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Hydrogen transfer; Kinetic; Metals Effect; Tempol; Trolox

Indexed keywords

ANTIOXIDANT; EDETIC ACID; FERROUS ION; FERROUS SULFATE; HYDROGEN; METAL ION; NITROXIDE; PENTETIC ACID; PHENOL; TEMPOL; TRANSITION ELEMENT; TROLOX C;

CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; ION TRANSPORT; OXIDATION REDUCTION REACTION; REVIEW;

ANTIOXIDANTS; CHROMANS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIC N-OXIDES; FREE RADICAL SCAVENGERS; FREE RADICALS; HYDROGEN; KINETICS; MODELS, CHEMICAL; OXYGEN; PENTETIC ACID; PHENOL; SPIN LABELS; TIME FACTORS;

EID: 0037363157     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/1071576031000081587     Document Type: Review

References (22)

1. Vogel, A.I. (1979) In: Spin Labeling II. Theory and Applications (Academic Press, New York, NY).
2. Borg, D.C. (1991) "Spin trapping and new developments in EPR: an overview", Oxidative Damage and Repair (Pergamon Press, New York, NY), pp 132-141.
3. Monti, E., Cova, D., Guido, E., Morelli, R. and Oliva, C. (1996) "Protective effects of the nitroxide TEMPOL against the cardiotoxicity of adriamycin", Free Radic. Biol. Med. 21, 463-470.
4. Krishna, M.C. and Samuni, A. (1994) "Nitroxide as antioxidants", Methods Enzymol. 234, 580-589.
5. Belkin, S., Mehlhorn, R., Hideg, K., Hankovsky, O. and Packer, L. (1987) "Reduction and destruction rates of nitroxide spin probes", Arch. Biochem. Biophys. 256, 232-243.
6. Fuchs, J., Groth, N., Herrling, T. and Zimmer, G. (1987) "Electron paramagnetic resonance studies on nitroxide radical Tempo redox reactions in human skin", Free Radic. Biol. Med. 22, 967-976.
7. Togashi, J.H., Shinzawa, H., Matsuo, T., Takeda, Y., Takahashi, T., Aoyama, M., Oikawa, K. and Kamada, H. (2000) "Analysis of hepatic oxidative stress status by electron spin resonance spectroscopy and imaging", Free Radic. Biol. Med. 28, 846-853.
8. Couet, W.R., Brasch, R.C., Sosnovsky, G. and Tozer, T.N. (1985) "Factors affecting nitroxide reduction in ascorbate solution and tissue homogenates", Magn. Reson. Imaging 3, 83-88.
9. Morris, S., Sosnovsky, G., Hui, B., Huber, C.O., Rao, N.U.M. and Swartz, H.M. (1991) "Chemical and electrochemical reduction rates of cyclic nitroxides", J. Pharm. Sci. 80, 149-152.
10. Schwartz, M.A., Parc, J.M. and Mc Connell, H.M. (1979) "Hydrogen atom exchange between nitroxides and hydroxylamines", J. Am. Chem. Soc. 101, 3592-3597.
11. Lissi, E.A., Rubio, M.A., Araya, D. and Zanocco, G. (1980) "Reaction of di-tert-butylnitroxide radicals", Int. J. Chem. Kinet. 12, 871-881.
12. Cáceres, T., Urzúa, C. and Lissi, E.A. (1985) "Decomposition of di-tert-butylnitroxide in aqueous solutions", Int. J. Chem. Kinet. 17, 109-116.
13. Glebska, J. and Gwozdzinski, K. (1998) "Effects of redox-active metals on antioxidant properties of nitroxides", Rev. Farm. Bioquím. Univ. Sao Paulo 34, 103.
14. Cáceres, T., Lissi, E.A. and Sanhueza, E. (1978) "Autoxidation of diethyl hydroxylamine", Int. J. Chem. Kinet. 10, 1167-1182.
15. Finkelstein, E., Rosen, G.M. and Rauckman, E.J. (1984) "Superoxide-dependent reduction of nitroxides by thiols", Biochim. Biophys. Acta 802, 90-98.
16. Hiramoto, K., Ojima, N. and Kikugawa, K. (1997) "Conversion of nitroxide radicals by phenolic and thiol antioxidants", Free Radic. Res. 27, 45-53.
17. WAF1/CIP1, and cell death in HL60 cells", Free Radic. Biol. Med. 29, 633-641.
18. Vogel, A.I., (1989) In: Practical Organic Chemistry (Longmans, London).
19. Hoffman, B.M. and Eames, T.B. (1969) "Protonated nitroxide free radical", J. Am. Chem. Soc. 91, 2169-2170.
20. Yamauchi, R., Kato, K. and Ueno, Y. (1988) "Formation of trimers of α-tocopherol and its model compound 2,2,5,7,8-pentamethylchroman-6-ol, in autoxidizing methyl linolate", Lipids 23, 779-783.
21. Janzen, E.G., Wilcox, A.L. and Manoharan, V. (1993) "Reaction of nitric oxide with phenolic antioxidants and phenoxyl radicals", J. Org. Chem. 58, 3597-3599.
22. Caceres, T., Urzúa, C. and Lissi, E.A. (1985) "Decomposition of di-tert-butyl nitroxide in aqueous solutions", Int. J. Chem. Kinet. 17, 109-116.