Synthesis, characterization, and evaluation of (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate as a biological agent and an anion sensor

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dc.authoridASLAN, KADIR/0000-0002-7617-0175
dc.authoridUnver, Huseyin/0000-0003-3968-4385
dc.authoridBoyacioglu, Bahadir/0000-0003-3757-3622
dc.authoridZeyrek, Celal Tugrul/0000-0001-6744-7841
dc.contributor.authorZeyrek, Celal Tugrul
dc.contributor.authorBoyacioglu, Bahadir
dc.contributor.authorYıldız, Mustafa
dc.contributor.authorUnver, Hilseyin
dc.contributor.authorYolal, Devrim
dc.contributor.authorDemir, Neslihan
dc.contributor.authorElmali, Ayhan
dc.date.accessioned2025-01-27T20:56:13Z
dc.date.available2025-01-27T20:56:13Z
dc.date.issued2016
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractAn amino acid based and bidentate Schiff base, (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate (ligand), was synthesized from the reaction of glycine-methyl ester hydrochloride with 2-hydroxy-l-naphthaldehyde. Characterization of the ligand was carried out using theoretical quantum -mechanical calculations and experimental spectroscopic methods. The molecular structure of the compound was confirmed using X-ray single-crystal data, NMR, FTIR and UV-Visible spectroscopy, which were in good agreement with the structure predicted by the theoretical calculations using density functional theory (DFT). Antimicrobial activity of the ligand was investigated for its minimum inhibitory concentration (MIC) to several bacteria and yeast cultures. UV-Visible spectroscopy studies also shown that the ligand can bind calf thymus DNA (CT-DNA) electrostatic binding. In addition, DNA cleavage study showed that the ligand cleaved DNA without the need for external agents. Energetically most favorable docked structures were obtained from the rigid molecular docking of the compound with DNA. The compound binds at the active site of the DNA proteins by weak non-covalent interactions. The colorimetric response of the ligand in DMSO to the addition of equivalent amount of anions (F-, Br-, I-, CN-, SCN-, ClO4-, HSO4-, AcO-, H2PO4-, N-3(-) and OH-) was investigated and the ligand was shown to be sensitive to CN- anion. (C) 2016 Elsevier Ltd. All rights reserved.
dc.description.sponsorshipAnkara University Grants Commission [16H0504001]
dc.description.sponsorshipThe authors are grateful to Ankara University Grants Commission for a research grant (Project No.: 16H0504001).
dc.identifier.doi10.1016/j.bmc.2016.09.018
dc.identifier.endpage5601
dc.identifier.issn0968-0896
dc.identifier.issn1464-3391
dc.identifier.issue21
dc.identifier.pmid27658791
dc.identifier.scopus2-s2.0-84991720136
dc.identifier.scopusqualityQ1
dc.identifier.startpage5592
dc.identifier.urihttps://doi.org/10.1016/j.bmc.2016.09.018
dc.identifier.urihttps://hdl.handle.net/20.500.12428/26342
dc.identifier.volume24
dc.identifier.wosWOS:000386990200061
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofBioorganic & Medicinal Chemistry
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectMolecular docking
dc.subjectDFT
dc.subjectGlycine-methyl ester hydrochloride
dc.subjectAnti-microbial activity
dc.subjectDNA binding
dc.subjectAnion sensor
dc.titleSynthesis, characterization, and evaluation of (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate as a biological agent and an anion sensor
dc.typeArticle

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