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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| Institution: | 1. Ankara Nuclear Research and Training Center, Turkish Atomic Energy Authority, TR-06100 Besevler-Ankara, Turkey;2. Vocational School of Health Services, Ankara University, TR-06290 Kecioren-Ankara, Turkey;3. Department of Chemistry, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, TR-17100 Çanakkale, Turkey;4. Department of Physics, Faculty of Science, Ankara University, 06100 Beşevler-Ankara, Turkey;5. Department of Biology, Faculty of Arts and Sciences, Çanakkale Onsekiz Mart University, TR-17100 Çanakkale, Turkey;6. Department of Physics Engineering, Faculty of Engineering, University of Ankara, TR-06100 Besevler-Ankara, Turkey;7. Morgan State University, Department of Chemistry, 1700 East Cold Spring Lane, Baltimore, MD 21251, USA;1. International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan;2. School of Chemical and Biomolecular Engineering, The University of Sydney, Darlington, NSW 2006, Australia;3. Department of Chemistry, College of Science, King Saud University, Riyadh 11451, Saudi Arabia;4. School of Natural Sciences, Griffith University, Nathan, QLD 4111, Australia;5. Australian Institute for Innovative Materials (AIIM), University of Wollongong, Squires Way, North Wollongong, NSW 2500, Australia;1. Department of Chemistry, University of Central Arkansas, Conway, AR 72035, USA;2. Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA;3. Department of Chemistry & Physics, University of South Carolina-Aiken, Aiken, SC 29801, USA;1. College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, PR China;2. Institute of Quality and Standard for Agro-products, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, PR China;1. Department of Chemistry, The University of Burdwan, Golapbag, Burdwan 713104, India;2. Department of Chemistry, Dr. Bhupendranath Dutta Smriti Mahavidyalaya, Burdwan 713407, West Bengal, India;1. Chemistry Department, Faculty of Science, King Abdulaziz University, 80203 Jeddah, Saudi Arabia;2. Chemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt;1. Department of Analytical Chemistry, Faculty of Chemistry, Razi University, Kermanshah, Iran;2. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran |
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| 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. |
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| Keywords: | Molecular docking DFT Glycine-methyl ester hydrochloride Anti-microbial activity DNA binding Anion sensor |
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