Synthesis, characterization, antimicrobial activity, 3D‐QSAR, DFT, and molecular docking of some ciprofloxacin derivatives and their copper(II) complexes,Applied Organometallic Chemistry

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Synthesis, characterization, antimicrobial activity, 3D‐QSAR, DFT, and molecular docking of some ciprofloxacin derivatives and their copper(II) complexes
Applied Organometallic Chemistry ( IF 3.7 ) Pub Date : 2020-10-10 , DOI: 10.1002/aoc.5998
Tarek E. Khalil ₁ , Ali El‐Dissouky ₁ , Dhuha Al‐Wahaib ₂ , Nada M. Abrar ₂ , Doaa S. El‐Sayed ₁

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Six new derivatives of ciprofloxacin compounds and their copper(II) complexes were synthesized, characterized by spectroscopic methods (ultraviolet–visible [UV–vis], Fourier transform infrared [FTIR], nuclear magnetic resonance [NMR], mass spectrometry [MS], and electron paramagnetic resonance [EPR]), and tested for antibacterial activities against gram‐negative and gram‐positive bacteria. The data showed that ciprofloxacin derivatives act as bidentate ligands and the metal ions coordinate through the pyridone carbonyl and the carboxylate oxygen atoms. Tetragonally distorted octahedral ligand fields were assumed for all complexes based on their spectral studies. Copper(II) complexes of the synthesized ciprofloxacin derivatives revealed higher antibacterial activities against gram‐positive and gram‐negative bacterial species than the parent ciprofloxacin antibiotic. Furthermore, three‐dimensional quantitative structure–activity relationship (3D‐QSAR) models were evaluated by studying 30 antibiotic compounds of the quinolone class. Density function theory (DFT) calculations were applied to evaluate the optimized geometrical structures using the B3LYP method and 6‐311G(d,p) basis set. The 3D‐QSAR study revealed that there are eight optimum parameters that give the best predictive modulation with good reliability (R² = 0.996, F = 12.004, sigma = 0.426). In silico molecular docking was also performed on the derivatives, and the results revealed the presence of two types of interactions between the Escherichia coli and the derivatives, H‐bonding and Van der Waals interactions, and an effective inhibition at the docked site.

中文翻译：

环丙沙星衍生物及其铜（II）配合物的合成，表征，抗菌活性，3D-QSAR，DFT和分子对接

合成了六种新的环丙沙星化合物及其铜（II）配合物衍生物，并通过分光光度法（紫外可见[UV-vis]，傅立叶变换红外[FTIR]，核磁共振[NMR]，质谱[MS]，和电子顺磁共振[EPR]），并测试了对革兰氏阴性和革兰氏阳性细菌的抗菌活性。数据表明环丙沙星衍生物充当双齿配体，金属离子通过吡啶酮羰基和羧酸根氧原子配位。根据它们的光谱研究，假定所有配合物都呈四边形扭曲的八面体配体场。合成的环丙沙星衍生物的铜（II）配合物对革兰氏阳性和革兰氏阴性细菌的抗菌活性高于母体环丙沙星抗生素。此外，通过研究30种喹诺酮类抗生素化合物，对三维定量构效关系（3D-QSAR）模型进行了评估。使用B3LYP方法和6-311G（d，p）基集，应用密度函数理论（DFT）计算来评估优化的几何结构。3D-QSAR研究表明，有八个最佳参数可提供最佳的预测调制并具有良好的可靠性（使用B3LYP方法和6-311G（d，p）基集，应用密度函数理论（DFT）计算来评估优化的几何结构。3D-QSAR研究表明，有八个最佳参数可提供具有良好可靠性的最佳预测调制（使用B3LYP方法和6-311G（d，p）基集，使用密度函数理论（DFT）计算来评估优化的几何结构。3D-QSAR研究表明，有八个最佳参数可提供最佳的预测调制并具有良好的可靠性（R ²＝ 0.996，F＝ 12.004，sigma ＝ 0.426）。还对衍生物进行了计算机分子对接，结果揭示了大肠杆菌和衍生物之间存在两种相互作用，即H键和范德华相互作用，以及对接位点的有效抑制。

更新日期：2020-11-06

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