Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 1163-1172 |
| Number of pages | 10 |
| Journal | Free Radical Research |
| Volume | 39 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2005 |
| Externally published | Yes |
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Free radical scavenging reactions of sulfasalazine, 5-aminosalicylic acid and sulfapyridine: Mechanistic aspects and antioxidant activity. / Joshi, R.; Kumar, S.; Unnikrishnan, M. et al.
In: Free Radical Research, Vol. 39, No. 11, 2005, p. 1163-1172.Research output: Contribution to journal › Article › peer-review
TY - JOUR
T1 - Free radical scavenging reactions of sulfasalazine, 5-aminosalicylic acid and sulfapyridine: Mechanistic aspects and antioxidant activity
AU - Joshi, R.
AU - Kumar, S.
AU - Unnikrishnan, M.
AU - Mukherjee, T.
N1 - Cited By :51 Export Date: 10 November 2017 CODEN: FRARE Correspondence Address: Joshi, R.; Radiation Chemistry and Chemical Dynamics Division, Chemistry Group, Bhabha Atomic Research Center, Mumbai 400 085, India; email: rjudrin@yahoo.com Chemicals/CAS: mesalazine, 89-57-6; salazosulfapyridine, 599-79-1; sulfapyridine, 144-83-2; superoxide, 11062-77-4; Aminosalicylic Acids; Anions; Antioxidants; Free Radical Scavengers; Free Radicals; Glutathione, 70-18-8; Hydroxyl Radical, 3352-57-6; Mesalamine, 89-57-6; Oxygen, 7782-44-7; Peroxides; Sulfapyridine, 144-83-2; Sulfasalazine, 599-79-1; trichloromethylperoxy radical, 69884-58-8 Manufacturers: Sigma References: Azad-Khan, A.H., Piris, J., Truelove, S.C., An experiment to determine the active therapeutic moiety of sulfasalazine (1977) Lancet, 2, pp. 892-895; Ardizzone, S., Porro, G.B., A practical guide to the management of distal ulcerative colitis (1998) Drugs, 55, pp. 519-542; Babbs, C.F., Oxygen radicals in ulcerative colitis (1992) Free Radic. 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Sci.), 99, pp. 261-271; Ahmad, S.A., (1997) Atomic, Molecular and Cluster Physics, , New Delhi: Narosa; Spinks, J.W.T., Woods, R.J., (1990) An Introduction to Radiation Chemistry, , New York: John Wiley; Buxton, G.V., Stuart, C.R., Re-evaluation of the thiocyanate dosimeter for pulse radiolysis (1995) J. Chem. Soc. Faraday Trans., 91, pp. 279-281; Buxton, G.V., Greenstock, C.L., Helman, W.P., Ross, A.B., Critical review of rate constants for reactions of the hydrated electrons, hydrogen atoms and hydroxyl radicals (OH/O ?) in aqueous solution (1988) J. Phys. Chem. Ref. Data, 17, pp. 513-886; Gordon, S., Schmidt, K.H., Hart, E.J., A pulse radiolysis study of aqueous benzene solutions (1977) J. Phys. Chem., 81, pp. 104-109; Alfassi, Z.B., Schuler, R.H., Reaction of azide radicals with aromatic compounds. Azide as a selective oxidant (1985) J. Phys. Chem., 89, pp. 3359-3363; Aruoma, O.I., Wasil, M., Halliwell, B., Hoey, B.M., Butler, J., The scavenging of oxidants by sulfasalazine and its metabolites. A possible contribution to their anti-inflammatory effects? (1987) Biochem. Pharmacol., 36, pp. 3739-3742; Motahashi, N., Saito, Y., Rate constants for reaction of hydroxyl radicals with sulfapyridine and aminosalicylic acid (1996) Chem. Pharm. Bull., 44, pp. 163-166; Solar, S., Getoff, N., Sehested, K., Holcman, J., Pulse radiolysis of pyridine carboxylic acids in aqueous solution (1991) Radiat. Phys. Chem., 38, pp. 323-332; Joshi, R., Kapoor, S., Mukherjee, T., Free radical reactions of pyridoxal (vitamin B6): A pulse radiolysis study (2002) Res. Chem. Intermed., 28, pp. 505-515; Das, T.N., Dhanasekaran, T., Alfassi, Z.B., Neta, P., Reduction potential of the tert-butyl peroxyl radical in aqueous solutions (1998) J. Phys. Chem. A., 102, pp. 280-284; Neta, P., Huie, R.E., Ross, A.B., Rate constants for reactions of peroxyl radicals in fluid solutions (1990) J. Phys. Chem. Ref. Data, 19, pp. 413-513; Packer, J.E., Slater, T.F., Wilson, R.L., Direct observation of a free radical interaction between vitamin E and C (1979) Nature, 278, pp. 737-738; 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 (1992) Biochem. Pharmacol., 43, pp. 259-262; 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 (1998) Arjzneimittel-Forschung, 48, pp. 1007-1011; Joshi, R., Mukherjee, T., Charge transfer between tryptophan and tyrosine in casein: A pulse radiolysis study (2002) Biophys. 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PY - 2005
Y1 - 2005
N2 - Reactions of sulfasalazine (SAZ) and its metabolites, 5-aminosalicylic acid (5-ASA) and sulfapyridine (SP), with various oxidizing and reducing free radicals (hydroxyl, haloperoxyl, one-electron oxidizing, lipid peroxyl, glutathiyl, superoxide, tryptophanyl, etc.) have been studied to understand the mechanistic aspects of its action against free radicals produced during inflammation. Nanosecond pulse radiolysis technique coupled with transient spectrophotometry has been used for in situ generation of free radicals and to follow their reaction pathways. The transients produced in these reactions have been assigned and radical scavenging rate constants have been measured. In addition to scavenging of various primary and secondary free radicals by SAZ, 5-ASA and SP, 5-ASA has also been observed to efficiently scavenge radicals of biomolecules. 5-ASA has been found to be the active moiety of SAZ involved in the scavenging of oxidizing free radicals whereas reduction of SAZ produced molecular radical anion. The study suggests that free radical scavenging activity of 5-ASA may be a major path of pharmacological action of SAZ against inflammatory bowel diseases (IBD). © 2005 Taylor & Francis.
AB - Reactions of sulfasalazine (SAZ) and its metabolites, 5-aminosalicylic acid (5-ASA) and sulfapyridine (SP), with various oxidizing and reducing free radicals (hydroxyl, haloperoxyl, one-electron oxidizing, lipid peroxyl, glutathiyl, superoxide, tryptophanyl, etc.) have been studied to understand the mechanistic aspects of its action against free radicals produced during inflammation. Nanosecond pulse radiolysis technique coupled with transient spectrophotometry has been used for in situ generation of free radicals and to follow their reaction pathways. The transients produced in these reactions have been assigned and radical scavenging rate constants have been measured. In addition to scavenging of various primary and secondary free radicals by SAZ, 5-ASA and SP, 5-ASA has also been observed to efficiently scavenge radicals of biomolecules. 5-ASA has been found to be the active moiety of SAZ involved in the scavenging of oxidizing free radicals whereas reduction of SAZ produced molecular radical anion. The study suggests that free radical scavenging activity of 5-ASA may be a major path of pharmacological action of SAZ against inflammatory bowel diseases (IBD). © 2005 Taylor & Francis.
U2 - 10.1080/10715760500177880
DO - 10.1080/10715760500177880
M3 - Article
SN - 1071-5762
VL - 39
SP - 1163
EP - 1172
JO - Free Radical Research
JF - Free Radical Research
IS - 11
ER -