Antioxidant activity of NSAID hydroxamic acids.
In the present study, seven hydroxamic acid derivatives of nonsteroidal anti-inflammatory drugs (NSAIDs) (ibuprofen, fenoprofen, ketoprofen, indomethacin and diclofenac) were found to possess significant antioxidant, radical scavenging and metal chelating activities. The most active antioxidant and radical scavenger was N-methylhydroxamic acid of diclofenac (ANT = 88.0% and EC50 = 60.1 microg mL-1). The activity of the standard substance, butylated hydroxyanisole, in the two assays was ANT = 86.9% and EC50 = 18.8 microg mL-1, respectively. Ibuproxam was the strongest iron chelator among investigated hydroxamic acids (EC50 = 255.6 microg mL-1), yet significantly weaker than the standard substance, EDTA (EC50 = 29.1 microg mL-1). It seems that different mechanism is involved in metal chelating activity than in antioxidant and radical scavenging activity. Antioxidant and radical scavenging activities may be connected with conjugation of the nitrogen lone electron pair with the carbonyl group. On the other hand, more hydrophilic substances tend to be better iron chelators.
Koncic
Marijana Zovko
MZ
Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia. mzovko@pharma.hr
Rajic
Zrinka
Z
Petric
Neva
N
Zorc
Branka
B
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000494:pharmacology; D006877:Hydroxamic Acids / Q000737:chemistry* / Q000494:pharmacology; D007502:Iron Chelating Agents / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010851:Picrates / Q000737:chemistry
D000894:Anti-Inflammatory Agents, Non-Steroidal; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D006877:Hydroxamic Acids; D007502:Iron Chelating Agents; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl