Free radical scavenging reactions of sulfasalazine, 5-aminosalicylic acid and sulfapyridine: Mechanistic aspects and antioxidant activity

Free Radical Research

Volumn 39, Issue 11, 2005, Pages 1163-1172

  Joshi, Ravi ^a   Kumar, Sudheer ^b   Unnikrishnan, M ^b   Mukherjee, T ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

^b MANIPAL COLLEGE OF PHARMACEUTICAL SCIENCES   (India)

Author keywords

5 aminosalicylic acid; Antioxidant; Free radicals; Kinetics and mechanism; Pulse radiolysis; Sulfasalazine

Indexed keywords

ANION; DRUG METABOLITE; FREE RADICAL; GLUTATHIONE DERIVATIVE; HYDROXYL GROUP; MESALAZINE; OXIDIZING AGENT; PEROXY RADICAL; SALAZOSULFAPYRIDINE; SULFAPYRIDINE; SUPEROXIDE; TRYPTOPHAN DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; ENTERITIS; INFLAMMATION; OXIDATION REDUCTION REACTION; PULSE RADIOLYSIS; SCAVENGING SYSTEM; SPECTROPHOTOMETRY;

AMINOSALICYLIC ACIDS; ANIONS; ANTIOXIDANTS; ELECTRONS; FREE RADICAL SCAVENGERS; FREE RADICALS; GLUTATHIONE; HYDROGEN-ION CONCENTRATION; HYDROXYL RADICAL; INFLAMMATION; INFLAMMATORY BOWEL DISEASES; KINETICS; LIPID PEROXIDATION; MESALAMINE; MODELS, CHEMICAL; OXYGEN; PEROXIDES; PULSE RADIOLYSIS; SPECTROPHOTOMETRY; SULFAPYRIDINE; SULFASALAZINE; TIME FACTORS;

EID: 27744455125     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760500177880     Document Type: Article

References (39)

1. Azad-Khan AH, Piris J, Truelove SC. An experiment to determine the active therapeutic moiety of sulfasalazine. Lancet 1977;2:892-895.
2. Ardizzone S, Porro GB. A practical guide to the management of distal ulcerative colitis. Drugs 1998;55:519-542.
3. Babbs CF. Oxygen radicals in ulcerative colitis. Free Radic Biol Med 1992;13:169-181.
4. Shanhan F, Targan S. Inflammatory bowel disease: From bench to bedside. Baltimore: Williams & Wilkens; 1994.
5. Oyanagui Y. Inhibition of superoxide anion production in macrophages by anti-inflammatory drugs. Biochem Pharmacol 1976;25:1473-1480.
6. Hiller KO, Wilson RL. Hydroxyl free radicals and anti-inflammatory drugs: Biological inactivation studies and reaction rate constants. Biochem Pharmacol 1983;32:2109-2111.
7. Peppercom MA, Goldman P. The role of intestinal bacteria in the metabolism of salicylazosulfapyridine. J Pharm Exp Ther 1972;181:555-562.
8. Miller DK, Gillard JW, Vickers PJ, Sadowski S, Leveille C, Mancini JA, Charleson P, Dixon RAF, Ford-Huthchinson AW, Fortin R, Gauthier JY, Rodkey J, Rosen R, Rouzer C, Sigal IS, Strader CD, Evans JF. Identification and isolation of a membrane protein necessary for leukotriene production. Nature 1990;343:278-281.
9. Packer L. Methods in enzymology. Vol. 234. San Diego: Academic Press; 1994. p 555-572.
10. Gionchetti P, Guarnieri C, Campieri M, Belluzzi A, Brignola C, Iannoe P, Miglioli M, Barbara L. Scavenger effects of sulfasalazine, 5-aminosalicylic acid, olsalazine on superoxide radical generation. Dig Dis Sci 1991;36:174-178.
11. Stevens C, Lipman M, Fabry S, et al. 5-Aminosalicylic acid abrogates T-cell proliferation by blocking interleukin 2 production in peripheral blood mononuclear cells. J Pharmacol Exp Ther 1995;272:399-406.
12. Cominell F, Zipser CA, Dinarello CA. Sulfasalazine inhibits cytokine production in human mononuclear cells: A novel anti-inflammatory mechanism. Gastroentrology 1992;96:A96.
13. Pronai L, Yukinobu I, Lang I, Feher J. The oxygen centered radical scavenging activity of sulfasalazine and its metabolites. A direct protection of bowel. Acta Physiol Hung 1992;80:317-323.
14. Yamada T, Volkmer C, Grisham MB. The effects of sulfasalazine metabolites on hemoglobin-catalyzed lipid peroxidation. Free Radic Biol Med 1991;10:41-49.
15. Baxendale JH, Busi F. The study of fast processes and transient species by electron pulse radiolysis. Dordrecht: D. Riedel; 1982.
16. Guha SN, Moorthy PN, Kishore K, Naik DB, Rao KN. Proc Ind Acad Sci (Chem Sci) 1987;99:261-271.
17. Ahmad SA. Atomic, molecular and cluster physics. New Delhi: Narosa; 1997.
18. Spinks JWT, Woods RJ. An Introduction to radiation chemistry. New York: John Wiley; 1990.
19. Buxton GV, Stuart CR. Re-evaluation of the thiocyanate dosimeter for pulse radiolysis. J Chem Soc Faraday Trans 1995;91:279-281.
20. Buxton GV, Greenstock CL, Helman WP, Ross AB. Critical review of rate constants for reactions of the hydrated electrons, hydrogen atoms and hydroxyl radicals (OH/O ?) in aqueous solution. J Phys Chem Ref Data 1988;17:513-886.
21. Gordon S, Schmidt KH, Hart EJ. A pulse radiolysis study of aqueous benzene solutions. J Phys Chem 1977;81:104-109.
22. Alfassi ZB, Schuler RH. Reaction of azide radicals with aromatic compounds. Azide as a selective oxidant. J Phys Chem 1985;89:3359-3363.
23. Aruoma OI, Wasil M, Halliwell B, Hoey BM, Butler J. The scavenging of oxidants by sulfasalazine and its metabolites. A possible contribution to their anti-inflammatory effects? Biochem Pharmacol 1987;36:3739-3742.
24. Motahashi N, Saito Y. Rate constants for reaction of hydroxyl radicals with sulfapyridine and aminosalicylic acid. Chem Pharm Bull 1996;44:163-166.
25. Solar S, Getoff N, Sehested K, Holcman J. Pulse radiolysis of pyridine carboxylic acids in aqueous solution. Radiat Phys Chem 1991;38:323-332.
26. Joshi R, Kapoor S, Mukherjee T. Free radical reactions of pyridoxal (vitamin B6): A pulse radiolysis study. Res Chem Intermed 2002;28:505-515.
27. Das TN, Dhanasekaran T, Alfassi ZB, Neta P. Reduction potential of the tert-butyl peroxyl radical in aqueous solutions. J Phys Chem A 1998;102:280-284.
28. Neta P, Huie RE, Ross AB. Rate constants for reactions of peroxyl radicals in fluid solutions. J Phys Chem Ref Data 1990;19:413-513.
29. Packer JE, Slater TF, Wilson RL. Direct observation of a free radical interaction between vitamin E and C. Nature 1979;278:737-738.
30. Allgayer H, Hofer P, Schmidt M, Bohne P, Kruis W, Gugler R. Superoxide, hydroxyl and fatty acid radical scavenging by aminosalicylate. Direct evaluation with electron spin resonance spectroscopy. Biochem Pharmacol 1992;43:259-262.
31. Kimura I, Kumamoto T, Matsuda A, Katoka M, Kokuba Y. Effects of BX661A, a new therapeutic agent for ulcerative colitis, on reactive oxygen species in comparison with salazosulfapyridine and its metabolite sulfapyridine. Arjzneimittel-Forschung 1998;48:1007-1011.
32. Joshi R, Mukherjee T. Charge transfer between tryptophan and tyrosine in casein: A pulse radiolysis study. Biophys Chem 2002;96:15-19.
33. Joshi R, Mukherjee T. Effect of solvent viscosity, polarity and pH on the charge transfer between tryptophan radical and tyrosine in bovine serum albumin: A pulse radiolysis study. Biophys Chem 2002;103:89-98.
34. Schöneich C, Asmus K-D. Reaction of thiyl radicals with alcohols, ethers and polyunsaturated fatty acids: A possible role of thiyl radicals in thiol mutagenesis? Radiat Environ Biophys 1990;29:263-271.
35. Stocker R, Frei B. Endogenous antioxidant defences in human blood plasma. In: Sies H, editor. Oxidative stress: Oxidants and antioxidants. London: Academic Press; 1991. p 213-243.
36. Schöneich C, Dillinger U, von Bruchhausen F, Asmus K-D. Oxidation of polyunsaturated fatty acids and lipids through thiyl and sulfonyl radicals: Reaction kinetics and influence of oxygen and structure of thiyl radicals. Arch Biochem Biophys 1992;292:456-467.
37. Surdhar SP, Armstrong D. Reduction potential and exchange reactions of thiyl radicals and disulfide anion radicals. J Phys Chem 1987;91:6532-6537.
38. .-, mediating electron transfer to Fe(III)-cytochrome c. Biophys Chem 1994; 49:101-110.
39. Schuler RH. Oxidation of ascorbate anion by electron transfer to phenoxyl radicals. Radiat Res 1977;69:417-433.