Polyphenols containing new azo-aroylhydrazone hybrids: theoretical insights and evaluation of antioxidant potential via CUPRAC and DPPH assays

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dc.contributor.authorYesil, Tolga Acar
dc.date.accessioned2026-04-25T14:19:55Z
dc.date.available2026-04-25T14:19:55Z
dc.date.issued2026
dc.departmentSinop Üniversitesi
dc.description.abstractThe growing interest in multifunctional antioxidants has drawn attention to hybrid scaffolds that unify distinct redox-active pharmacophores. Azo groups, aroylhydrazones, and gallic acid derivatives are individually recognized for their notable antioxidant potential, yet molecular hybrids integrating all three remain scarce. To address this gap, a new series of compounds (5a-j) combining azo, aroylhydrazone, and polyhydroxyphenyl moieties was designed and synthesized to enhance antioxidant activity through structural synergy. The synthesized molecules were thoroughly characterized by FTIR, 1H, 13C NMR, 2D NOESY/COSY, UV-Vis, and mass spectrometry. Their electronic and structural properties were further evaluated using DFT calculations at the B3LYP/6-311++G(d,p) level. In silico ADMEt predictions and molecular docking studies revealed favorable pharmacokinetic profiles and strong binding affinities toward key antioxidant-related enzymes-glutathione reductase (PDB: 1XAN), myeloperoxidase (PDB: 3F9P), and NAD(P)H oxidase (PDB: 2CDU). In vitro antioxidant activity was assessed using CUPRAC and DPPH assays, with Trolox serving as the standard. Remarkably, this is the first study to report the combined use of DMF in the CUPRAC and DMSO in the DPPH assays, offering a novel solvent strategy that enhanced compound solubility and assay compatibility. Among the tested compounds, 5b and 5e showed the highest antioxidant activities, surpassing Trolox in both methods. These results suggest that the azo-aroylhydrazone-polyphenol hybrid structure holds strong promise as a platform for developing nextgeneration antioxidant agents.
dc.description.sponsorshipScientific Research Projects of Sinop University [TMYO-1901-25-001]
dc.description.sponsorshipThis research was supported by the Scientific Research Projects of Sinop University (Project No: TMYO-1901-25-001) .
dc.identifier.doi10.1016/j.bioorg.2025.109377
dc.identifier.issn0045-2068
dc.identifier.issn1090-2120
dc.identifier.pmid41412066
dc.identifier.scopus2-s2.0-105025006066
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.bioorg.2025.109377
dc.identifier.urihttps://hdl.handle.net/11486/8259
dc.identifier.volume168
dc.identifier.wosWOS:001644208900001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorYesil, Tolga Acar
dc.language.isoen
dc.publisherAcademic Press Inc Elsevier Science
dc.relation.ispartofBioorganic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20260420
dc.subjectAroylhydrazone
dc.subjectCUPRAC
dc.subjectDPPH
dc.subjectMolecular docking
dc.subjectQuantum chemical calculations
dc.titlePolyphenols containing new azo-aroylhydrazone hybrids: theoretical insights and evaluation of antioxidant potential via CUPRAC and DPPH assays
dc.typeArticle

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