Antioxidant activity of NSAID hydroxamic acids

Scientific paper - Preliminary note / Short communication

• Title (croatian): Antioksidativno djelovanje NSAID hidroksamskih kiselina
• Author: Marijana Zovko Končić
• Author: Zrinka Rajić
• Author: Neva Petrić
• Author: Branka Zorc
• Author's institution: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of medicinal chemistry)
• Author's institution: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of pharmacognosy)
• Scientific / art field, discipline and subdiscipline: BIOMEDICINE AND HEALTHCARE; Pharmacy; Pharmacy

Abstract (english)

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.

Abstract (croatian)

U radu je opisano antioksidativno djelovanje te sposobnost hvatanja slobodnih radikala i stvaranja kelata sedam hidroksamskih kiselina, derivata nesteroidnih protuupalnih lijekova ibuprofena, fenoprofena, ketoprofena, indometacina i diklofenaka. Najjače antioksidativno djelovanje i najjaču sposobnost hvatanja slobodnih radikala imala je N-metilhidroksamska kiselina diklofenaka (ANT = 88,0 % i EC50 = 60,1 g mL1). Vrijednosti za standardnu supstanciju, butilirani hidroksianisol, bile su: ANT = 86,9 % i EC50 = 18,8 g mL1. Derivat ibuprofena bio je najjači kelator među ispitivanim hidroksamskim kiselinama (EC50 = 255,6 g mL1), ali značajno slabiji od standardne supstancije, EDTA (EC50 = 29,1 g mL1). Pretpostavlja se da su različiti mehanizmi uključeni u keliranje metala i antioksidativno djelovanje, odnosno hvatanje slobodnih radikala. Antioksidativno djelovanje i sposobnost hvatanja slobodnih radikala moglo bi biti povezano s konjugacijom slobodnog para elektrona na dušiku s karbonilnom skupinom. S druge strane, hidrofilnije supstancije pokazale su se kao jači kelatori iona željeza.

• Keywords (english): NSAID; hydroxamic acid; antioxidant activity; radical scavenging activity; metal chelating ability
• Keywords (croatian): NSAID; hidroksamska kiselina; antioksidativno djelovanje; vezanje slobodnih radikala; sposobnost keliranja metala
• Language: english
• Publication type: Scientific paper - Preliminary note / Short communication
• Publication status: Published
• Peer review: Peer review - international
• Publication version: Published version
• Journal title: Acta Pharmaceutica
• Numbering: vol. 59, no. 2, pp. 235-242
• p-ISSN: 1330-0075
• e-ISSN: 1846-9558
• DOI: https://doi.org/10.2478/v10007-009-0017-8
• URN:NBN: urn:nbn:hr:163:459116
• Publication: 2009-06-01
• Document URL: https://hrcak.srce.hr/35243
• Type of resource: Text
• Access conditions: Open access
• Created on: 2018-02-14 13:34:28