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.contributor.authorZeyrek, C. Tuğrul
dc.contributor.authorBoyacıoğlu, Bahadır
dc.contributor.authorYıldız, Mustafa
dc.contributor.authorÜnver, Hüseyin
dc.contributor.authorYolal, Devrim
dc.contributor.authorDemir, Neslihan
dc.contributor.authorElmalı, Ayhan
dc.contributor.authorAslan, Kadir
dc.contributor.authorID0000-0001-6744-7841tr_TR
dc.contributor.departmentTAEK-ANAEMtr_TR
dc.date.accessioned2018-11-26T08:06:14Z
dc.date.available2018-11-26T08:06:14Z
dc.date.issued2016
dc.description.abstractAn amino acid derived 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-1-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-, N3- and OH-) was investigated and the ligand was shown to be sensitive to CN- anion.tr_TR
dc.identifier.citationZeyrek, C. T. ... [ve arkadaşları]. (2016). Synthesis, characterization, and evaluation of (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate as a biological agent and an anion sensor. Bioorganic & Medicinal Chemistry, 24(21), 5592-5601.tr_TR
dc.identifier.endpage5601tr_TR
dc.identifier.issn0968-0896tr_TR
dc.identifier.issue21tr_TR
dc.identifier.startpage5592tr_TR
dc.identifier.urihttps://www.sciencedirect.com/science/article/pii/S0968089616307052?via%3Dihub
dc.identifier.urihttp://kurumsalarsiv.tenmak.gov.tr/handle/20.500.12878/981
dc.identifier.volume24tr_TR
dc.language.isoengtr_TR
dc.publisherElseviertr_TR
dc.relation.isversionofhttps://doi.org/10.1016/j.bmc.2016.09.018tr_TR
dc.relation.journalBioorganic & Medicinal Chemistrytr_TR
dc.rightsinfo:eu-repo/semantics/openAccesstr_TR
dc.subjectMolecular dockingtr_TR
dc.subjectMoleküler kenetlemetr_TR
dc.subjectAnti-microbial activitytr_TR
dc.subjectAnti-mikrobiyal aktivititr_TR
dc.subjectAnion sensortr_TR
dc.subjectAnyon algılayıcıtr_TR
dc.subjectX-raystr_TR
dc.subjectX-ışınlarıtr_TR
dc.subjectDFTtr_TR
dc.subjectDNAtr_TR
dc.titleSynthesis, characterization, and evaluation of (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate as a biological agent and an anion sensortr_TR
dc.typearticletr_TR
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