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dc.creatorMilanović, Ziko
dc.creatorDimic, Dusan
dc.creatorŽižić, Milan
dc.creatorMilenković, Dejan
dc.creatorMarković, Zoran
dc.creatorAvdović, Edina
dc.date.accessioned2022-04-05T15:38:53Z
dc.date.available2022-04-05T15:38:53Z
dc.date.issued2021
dc.identifier.issn1422-0067
dc.identifier.urihttp://rimsi.imsi.bg.ac.rs/handle/123456789/1504
dc.description.abstractCoumarin derivatives have proven beneficial biological activities, but the mechanism of their radical scavenging potency is not fully understood. In this study, the antiradical capacity of two newly synthesized 4,7-dihydroxycoumarin derivatives: (E)-3-(1-((3-hydroxy-4-methoxyphenyl)amino)-ethylidene)-2,4-dioxochroman-7-yl acetate (A-3OH) and (E)-3-(1-((4-hydroxy-3-methoxyphenyl)amino)ethylidene)-2,4-dioxochroman-7-yl acetate (A-4OH) towards HO center dot were examined by Electron Paramagnetic Resonance (EPR) Spectroscopy and Density Functional Theory (DFT). The compounds were fully characterized by the elemental microanalysis, IR, and NMR spectroscopies. The effect of pH on the acid-base equilibria is separately discussed and the predominant species at the physiological pH were determined. Several common mechanisms (Hydrogen Atom Transfer (HAT), Single-Electron Transfer followed by Proton Transfer (SET-PT), Sequential Proton Loss followed by Electron Transfer (SPLET), Radical Adduct Formation (RAF), and Intramolecular Hydrogen Atom Abstraction (iHAA)) of radical scavenging were investigated based on thermodynamic and kinetic parameters. EPR results indicated that both compounds significantly reduce the amount of present HO center dot. The results of the kinetic DFT study demonstrated that both compounds predominantly exhibit antiradical capacity through HAT and SPLET mechanisms. The estimated overall rate constants (k(overall)) proved that A-4OH shows better antioxidant capacity than A-3OH which is well-correlated with the results obtained by EPR measurement.en
dc.publisherMDPI, Basel
dc.relationEIT's HEI Initiative SMART-2M project
dc.relationEIT Raw Materials
dc.relationEuropean UnionEuropean Commission
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.sourceInternational Journal of Molecular Sciences
dc.subjectradical scavengingen
dc.subjectQM-ORSAen
dc.subjecthydroxy radicalen
dc.subjectEPRen
dc.subjectDFTen
dc.subjectantiradical activityen
dc.subject7-dihydroxycoumarinen
dc.subject4en
dc.titleMechanism of Antiradical Activity of Newly Synthesized 4,7-Dihydroxycoumarin Derivatives-Experimental and Kinetic DFT Studyen
dc.typearticle
dc.rights.licenseBY
dc.citation.issue24
dc.citation.other22(24): -
dc.citation.rankM21~
dc.citation.volume22
dc.identifier.doi10.3390/ijms222413273
dc.identifier.fulltexthttp://rimsi.imsi.bg.ac.rs/bitstream/id/419/1501.pdf
dc.identifier.pmid34948070
dc.identifier.scopus2-s2.0-85120802238
dc.identifier.wos000738585600001
dc.type.versionpublishedVersion


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Приказ основних података о документу