Quenching of reactive oxidative species by probucol and comparison with other antioxidants

Free Radical Biology and Medicine

Volumn 20, Issue 3, 1996, Pages 411-420

  Bisby, Roger H ^a   Johnson, Steven A ^a   Parker, Anthony W ^b  

^a UNIVERSITY OF SALFORD   (United Kingdom)

^b RUTHERFORD APPLETON LABORATORY   (United Kingdom)

Author keywords

Antioxidant; Flash photolysis; Free radical; Oxidation; Probucol; Pulse radiolysis; Raman; Singlet oxygen

Indexed keywords

ACETYLCYSTEINE; ALPHA TOCOPHEROL; ANTIOXIDANT; ASCORBIC ACID DERIVATIVE; DIHYDROLIPOATE; PROBUCOL; REACTIVE OXYGEN METABOLITE; SINGLET OXYGEN;

ARTICLE; ATHEROSCLEROSIS; DRUG ACTIVITY; DRUG EFFECT; DRUG SCREENING; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; RAMAN SPECTROMETRY;

EID: 0029923047     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/0891-5849(95)02094-2     Document Type: Article

References (41)

1. Kuzuya, M.; Kuzuya, F. Probucol as an antioxidant and antiatherogenic drug. Free Radic. Biol. Med. 14:67-77; 1993.
2. Barnhart, R. L.; Busch, S. J.; Jackson, R. L. Concentration-dependent antioxidant activity of probucol in low density lipoproteins in vitro: Probucol degradation precedes lipoprotein oxidation. J. Lipid Res. 30:1703-1710; 1989.
3. Breugnot, C.; Maziere, C.; Salmon, S.; Auclair, M.; Santus, R.; Morliere, P.; Lenaers, A.; Maziere, J. C. Phenothiazines inhibit copper and endothelial cell-induced peroxidation of low density lipoprotein. Biochem. Pharmacol. 40:1975-1980; 1990.
4. Esterbauer, H.; Gebicki, J.; Puhl, H.; Jurgens, G. The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radic. Biol. Med. 13:341-390; 1992.
5. Hanna, A. N.; Feller, D. R.; Witiak, D. T.; Newman, H. A. I. Inhibition of low density lipoprotein oxidation by thyronines and probucol. Biochem. Pharmacol. 45:753-762; 1993.
6. Pryor, W. A.; Strickland, T.; Church, D. F. Comparison of the efficiencies of several natural and synthetic antioxidants in aqueous sodium dodecyl sulfate micelle solution. J. Am. Chem. Soc. 110:2224-2229; 1988.
7. Darley-Usmar, V. M.; Hersey, A.; Garland, L. G. A method for the comparative assessment of antioxidants as peroxyl radical scavengers. Biochem. Pharmacol. 38:1465-1469; 1989.
8. Thomas, C. E.; McLean, L. R.; Parker, R. A.; Ohlweiler, D. F. Ascorbate and phenolic antioxidants in prevention of liposomal oxidation. Lipids 27:543-550; 1992.
9. Hiramatsu, M.; Liu, J.; Edamatsu, R.; Ohba, S.; Kadowaki, D.; Mori, A. Probucol scavenged 1,1-diphenyl-2-picrylhydrazyl radicals and inhibited formation of thiobarbituric acid reactive substances. Free Radic. Biol. Med. 16:201-206; 1994.
10. Buettner, G. The pecking order of free radicals and antioxidants: Lipid oxidation, α-tocopherol and ascorbate. Arch. Biochem. Biophys. 300:535-543; 1993.
11. Kalyanaraman, B.; Darley-Usmar, V. M.; Wood, J.; Joseph, J.; Parthasarathy, S. Synergistic interaction between the probucol phenoxyl radical and ascorbic acid in inhibiting the oxidation of low density lipoprotein. J. Biol. Chem. 267:6789-6795; 1992.
12. Bensasson, R. V.; Land, E. J.; Truscott, T. G. Flash photolysis and pulse radiolysis. Oxford: Pergamon Press; 1983.
13. Tripathi, G. N. R. Time-resolved resonance Raman spectroscopy of chemical reaction intermediates in solution. In: Clark, R. J. H.; Hester, R. E., eds. Time resolved spectroscopy. London: Wiley; 1989:157-218.
14. Wardman, P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J. Phys. Chem. Ref. Data 18:1637-1755; 1989.
15. Parker, A. W.; Hester, R. E.; Phillips, D.; Umapathy, S. Time-resolved resonance Raman spectroscopic investigations of the photochemistry of ubiquinone. J. Chem. Soc. Faraday Trans. 88:2694-2653; 1992.
16. Bisby, R. H.; Ahmed, S.; Cundall, R. B.; Thomas, E. W. Free radical reactions with alpha-tocopherol and N-stearoyl tryptophan methyl ester in micellar solutions. Free Radic. Res. Commun. 1:251-261; 1986.
17. Porter, G.; Wilkinson, F. Primary photochemical processes in aromatic molecules. Part 5 - Flash photolysis of benzophenone in solution. Trans. Faraday Soc. 57:1686-1691; 1961.
18. Scheerer, R.; Gratzel, M. Laser photolysis studies of duroquinone triplet state electron transfer reactions. J. Am. Chem. Soc. 99:865-871; 1977.
19. Encinas, M. V.; Lissi, E. A.; Olea, A. F. Quenching of triplet benzophenone by vitamins E and C and by sulphur containing amino acids and peptides. Photochem. Photobiol. 42:347-352; 1985.
20. Patel, K. B.; Willson, R. L. Semiquinone free radicals and oxygen: Pulse radiolysis study of one-electron transfer equilibria. J. Chem. Soc. Faraday Trans. I 69:814-825; 1973.
21. Bisby, R. H.; Cundall, R. B.; Davies, A. K. Aspects of chemical damage in radiation and photo-biology. Photochem. Photobiol. 28:825-837; 1978.
22. McCubbin, I.; Phillips, D.; Hester, R. E. Time-resolved resonance Raman spectroscopy of the triplet state and semi-reduced form of duroquinone. J. Chem. Soc., Faraday Trans. 83:1519-1524; 1987.
23. Bisby, R. H.; Parker, A. W. Reactions of excited triplet duroquinone with α-tocopherol and ascorbate: A nanosecond laser flash photolysis and time-resolved resonance Raman investigation. J. Am. Chem. Soc. 117:5664-5670; 1995.
24. Hester, R. E.; Williams, K. P. J. Resonance Raman studies of the p-benzosemiquinone and p,p′-biphenylsemiquinone free radical anions. J. Chem. Soc., Faraday Trans. 78:573-584; 1982.
25. Tripathi, G. N. R.; Schuler, R. H. Resonance Raman spectra of p-benzosemiquinone radical and hydroquinone radical cation. J. Phys. Chem. 91:5881-5885; 1987.
26. Tripathi, G. N. R.; Schuler, R. H. Resonance Raman studies of substituent effects on the electronic structure of phenoxyl radicals. J. Phys. Chem. 92:5129-5133; 1988.
27. Parker, A. W.; Bisby, R. H. Time-resolved resonance Raman spectroscopy of α-tocopheroxyl and related radicals in solvent, micellar and membrane systems. J. Chem. Soc. Faraday Trans. 89:2873-2878; 1993.
28. Tripathi, G. N. R.; Schuler, R. H. The resonance Raman spectrum of phenoxyl radical. J. Chem. Phys. 81:113-121; 1984.
29. Johnson, C. R.; Ludwig, M.; Asher, S. A. Ultraviolet resonance Raman characterization of photochemical transients of phenol, tyrosine and tryptophan. J. Am. Chem. Soc. 108:905-912; 1986.
30. Tripathi, G. N. R.; Sun, Q.; Armstrong, D. A.; Chipman, D. M.; Schuler, R. H. Resonance Raman spectra and structure of the phenylthiyl radical. J. Phys. Chem. 96:5344-5350; 1992.
31. Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols. J. Am. Chem. Soc. 107:7053-7065; 1985.
32. Zahalka, H. A.; Robillard, B.; Hughes, L.; Lusztyk, J.; Burton, G. W.; Janzen, E. G.; Kotake, Y.; Ingold, K. U. Antioxidant activity of 1-thio-α-tocopherol and related compounds. J. Org. Chem. 53:3739-3745; 1988.
33. Armstrong, D. A.; Sun, Q.; Tripathi, G. N. R.; Schuler, R. H. Spectra, ionization constants, and rates of oxidation of 1,4-dimercaptobenzene and properties of the p-mercaptophenylthiyl and p-benzodithiyl anion radicals. J. Phys. Chem. 97:5611-5617; 1993.
34. Packer, L. New horizons in antioxidant research: Action of the thioctic acid/dihydrolopoic acid couple in biological systems. In: Schmidt, K.; Ulrich, H., eds. Second international thioctic acid workshop. Frankfurt am Main: Universimed-Verlag; 1991:35-44.
35. Darmanyan, A. P.; Foote, C. S. Solvent effects on singlet oxygen yield from n,π* and π,π* triplet carbonyl compounds. J. Phys. Chem. 97:5032-5035; 1993.
36. Gorman, A. A. The bimolecular reactivity of singlet molecular oxygen. Adv. Photochem. 17:217-274; 1992.
37. DiMascio, P.; Devasagayam, T. P. A.; Kaiser, S.; Sies, H. Carotenoids, tocopherols and thiols as biological singlet molecular oxygen quenchers. Biochem. Soc. Trans. 18:1054-1056; 1990.
38. Chou, P.-T.; Khan, A. U. L-Ascorbic acid quenching of singlet delta molecular oxygen in aqueous media-generalized antioxidant property of vitamin C. Biochem. Biophys. Res. Commun. 115:932-937; 1983.
39. Rooney, M. L. Ascorbic acid as a photo-oxidation inhibitor. Photochem. Photobiol. 38:619-621; 1983.
40. Buettner, G. R.; Hall, R. D. Superoxide, hydrogen peroxide and singlet oxygen in hematoporphyrin derivative-cysteine, derivative-NADH and derivative-light systems. Biochim. Biophys. Acta 923:501-507; 1987.
41. Packer, L.; Witt, E. H.; Tritschler, H. J. Alpha-lipoic acid as a biological antioxidant. Free Radic. Biol. Med. 19:227-250; 1995.