A rapid synthesis of 2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid: Experimental, DFT study and DNA cleavage activity
| Autor: | Fatih Duman, Tahir Tilki, Sevgi Özdemir Kart, Merve Gökalp, Çiğdem Karabacak Atay |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
pBR322 DNA cleavage
Electrophoresis Computation theory Computational chemistry 010402 general chemistry Spectroscopic analysis 01 natural sciences Computational geometry Analytical Chemistry Agarose gel electrophoresis Inorganic Chemistry chemistry.chemical_compound DNA double helices Heterocyclic dye Anthranilic acid Thermal analysis techniques Benzoic acid Spectroscopic property Spectroscopy Nuclear magnetic resonance spectroscopy Disruptive effects DNA cleavage Mass spectrometry 010405 organic chemistry Chemical shift Organic Chemistry DNA Thermoanalysis 0104 chemical sciences Crystallography chemistry Proton NMR Mass spectrum Density functional theory Quantum chemistry Spectroscopic measurements |
| DOI: | 10.1016/j.molstruc.2018.06.032 |
| Popis: | The newly synthesized 2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid has been prepared by diazotization of anthranilic acid and coupling with 2-amino-4,6-dimethylpyrimidine. Its structure has been characterized by spectroscopic measurements (1H NMR spectra, FT-IR spectra, mass spectra and UV–visible spectra) and thermal analysis technique. The DNA cleavage activity of compound is evaluated by agarose gel electrophoresis with a series of concentrations. Our measurements show that neither a disruptive effect created by 2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid on pBR 322 DNA are observed, nor the dependence of the concentration on the activity of newly synthetized chemical on pBR 322 plasmid DNA such as cleavage or break DNA double helix structure. Moreover, computational chemistry method based on Density Functional Theory (DFT) employing B3LYP level with 6-31G(d) basis set has been used to study geometry and spectroscopic properties such as FT-IR and UV–vis spectra of the titled compound considered in this work. The computations of the chemical shifts for 1H NMR of the title compound have been carried out via Gauge-Invariant Atomic Orbital (GIAO) method utilizing the same basis set. It is observed that DFT results are compatible with the experimental results. © 2018 Elsevier B.V. |
| Databáze: | OpenAIRE |
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