Synthesis, Biological Activities, Antioxidant Properties, and Molecular Docking Studies of Novel Bis-Schiff Base Podands as Responsive Chemosensors for Anions

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dc.authoridYalcin, Gozde/0000-0002-9689-2239
dc.authoridKiraz, Askin/0000-0002-2350-8291
dc.contributor.authorYapar, Gonul
dc.contributor.authorDemir, Neslihan
dc.contributor.authorKiraz, Askin
dc.contributor.authorOzkat, Gozde Yalcin
dc.contributor.authorYıldız, Mustafa
dc.date.accessioned2025-01-27T21:02:13Z
dc.date.available2025-01-27T21:02:13Z
dc.date.issued2022
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractIn this study, bis-carbonyl podand (triethylene glycol bis(2-carbonylphenyl)ether) ( 1 ) was synthesized from the reaction of triethylene glycol dichloride with salicylaldehyde. Then, Schiff base podans ( 2 and 3 ) were prepared from the interaction of bis(carbonyl) podand with 2-amino-4-methylphenol and 2-amino3-hydroxypyridine in ethanol medium. The structures of podands have been investigated by elementary analysis, FT-IR, UV-Vis,H- 1-NMR, C-13-NMR and MS spectroscopy. The antimicrobial activities of the podands have been investigated for their minimum inhibitory concentration (MIC) to bacteria and yeast cultures. Furthermore, the interactions of Schiff base podands with DNA were investigated by UV-Vis spectra and gel electrophoresis method. The efficiency of molecules in DNA cleavage has also been investigated by computational examination of the interaction between Schiff base podands and human topoisomerase II alpha (hTop alpha) enzyme by molecular docking method. Docking results of podands were compared with known topo inhibitors. UV-Vis spectroscopy studies of the interactions between the podands and calf thymus DNA (CT-DNA) showed that the compounds interact with CT-DNA via electrostatic binding. DNA cleavage study showed that the podands cleaved DNA oxidatively. It has been observed that especially podand 2 shows the best interactions with the hTop alpha's binding site by molecular docking method compared to known inhibitors. In addition, antioxidant activities of Schiff base podands were measured using the DPPH method. Podands showed similar antioxidant activity with BHT. It was also found that activity increased with increasing concentration of compounds. In addition, the anion recognition ability of all Schiff bases was examined by colorimetric, UV-Vis and fluorescence spectroscopy. Schiff base podand 2 showed a visually and spectroscopically detectable color and absorbance change against fluoride, cyanide and hydroxyl anions, while Schiff base podand 3 showed the same change against fluoride, cyanide, acetate, dihydrogen phosphate and hydroxyl anions. No significant color and absorbance change were observed upon addition of other anions such as bromide, iodide, thiocyanate, perchlorate, and hydrogen sulphate.(c) 2022 Elsevier B.V. All rights reserved.
dc.description.sponsorshipIstanbul Technical University [33467]
dc.description.sponsorshipThe authors thank Istanbul Technical University Grants Commission for a research grant (Project No: 33467).
dc.identifier.doi10.1016/j.molstruc.2022.133530
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85132748442
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.133530
dc.identifier.urihttps://hdl.handle.net/20.500.12428/27310
dc.identifier.volume1266
dc.identifier.wosWOS:000822689500005
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectSchiff base
dc.subjectpodand
dc.subjecttautomerism
dc.subjectanion sensors
dc.subjectcalf thymus-DNA
dc.subjectantioxidant
dc.subjectmolecular docking
dc.titleSynthesis, Biological Activities, Antioxidant Properties, and Molecular Docking Studies of Novel Bis-Schiff Base Podands as Responsive Chemosensors for Anions
dc.typeReview Article

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