title: Synthesis, characterization, and evaluation of (E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate as a biological agent and an anion sensor.
abstract: An 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-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.
authors.affiliation: Ankara Nuclear Research and Training Center, Turkish Atomic Energy Authority, TR-06100 Besevler-Ankara, Turkey.
authors.forename: Celal Tuğrul
authors.initials: CT
authors.lastname: Zeyrek
authors.affiliation: Vocational School of Health Services, Ankara University, TR-06290 Kecioren-Ankara, Turkey.
authors.forename: Bahadir
authors.initials: B
authors.lastname: Boyacioğlu
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, TR-17100 Çanakkale, Turkey. Electronic address: myildiz@comu.edu.tr.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Yıldız
authors.affiliation: Department of Physics, Faculty of Science, Ankara University, 06100 Beşevler-Ankara, Turkey.
authors.forename: Hüseyin
authors.initials: H
authors.lastname: Ünver
authors.affiliation: Department of Physics, Faculty of Science, Ankara University, 06100 Beşevler-Ankara, Turkey.
authors.forename: Devrim
authors.initials: D
authors.lastname: Yolal
authors.affiliation: Department of Biology, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, TR-17100 Çanakkale, Turkey.
authors.forename: Neslihan
authors.initials: N
authors.lastname: Demir
authors.affiliation: Department of Physics Engineering, Faculty of Engineering, University of Ankara, TR-06100 Besevler-Ankara, Turkey.
authors.forename: Ayhan
authors.initials: A
authors.lastname: Elmali
authors.affiliation: Morgan State University, Department of Chemistry, 1700 East Cold Spring Lane, Baltimore, MD 21251, USA.
authors.forename: Solomon
authors.initials: S
authors.lastname: Tadesse
authors.affiliation: Morgan State University, Department of Chemistry, 1700 East Cold Spring Lane, Baltimore, MD 21251, USA. Electronic address: kadir.aslan@morgan.edu.
authors.forename: Kadir
authors.initials: K
authors.lastname: Aslan
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000838:Anions / Q000032:analysis; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D002417:Cattle; D003486:Cyanides / Q000032:analysis*; D004247:DNA / Q000187:drug effects; D053837:DNA Cleavage; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011789:Quantum Theory; D012441:Saccharomyces cerevisiae / Q000187:drug effects*; D055672:Static Electricity; D013329:Structure-Activity Relationship
chemical_list: C000621635:(E)-methyl 2-((2-oxonaphthalen-1(2H)-ylidene)methylamino)acetate; D000085:Acetates; D000838:Anions; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003486:Cyanides; D009281:Naphthalenes; D004247:DNA; C427203:calf thymus DNA
keywords: Anion sensor; Anti-microbial activity; DFT; DNA binding; Glycine-methyl ester hydrochloride; Molecular docking