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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• 作者：Celal Tuğrul Zeyrek^a ; Bahadir Boyacioğlu^b ; Mustafa Yıldız^c ; ^{myildiz@comu.edu.tr" class="auth_mail" title="E-mail the corresponding author} ; H&uuml ; seyin &Uuml ; nver^d ; Devrim Yolal^d ; Neslihan Demir^e ; Ayhan Elmali^f ; Solomon Tadesse^g ; Kadir Aslan^g ; ^{kadir.aslan@morgan.edu" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Molecular docking ; DFT ; Glycine-methyl ester hydrochloride ; Anti-microbial activity ; DNA binding ; Anion sensor
• 刊名：Bioorganic & Medicinal Chemistry
• 出版年：2016
• 出版时间：1 November 2016
• 年：2016
• 卷：24
• 期：21
• 页码：5592-5601
• 全文大小：2137 K

文摘

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⁻, ClOb>4b>⁻, HSOb>4b>⁻, AcO⁻, Hb>2b>POb>4b>⁻, Nb>3b>⁻ and OH⁻) was investigated and the ligand was shown to be sensitive to CN⁻ anion.