基于喹啉的柔性酰胺受体的 Cu(II)和 Zn(II)配合物的合成作为用于二氢膦酸和硫酸氢根的荧光探针及其抗菌活性。

Synthesis of Cu (II) and Zn (II) Complexes of a Quinoline Based Flexible Amide Receptor as Fluorescent Probe for Dihydrogen Phosphate and Hydrogen Sulphate and Their Antibacterial Activity.

机构信息

Department of Chemistry, University of North Bengal, Raja Rammohunpur, Darjeeling, 734013, India.

Department of Chemistry, Faculty of Engineering & Technology, Veer Bahadur Singh Purvanchal University, Jaunpur, Uttar Pradesh, 222003, India.

出版信息

J Fluoresc. 2024 Jul;34(4):1829-1840. doi: 10.1007/s10895-023-03416-8. Epub 2023 Aug 30.

Abstract

A novel 8-hydroxy quinoline-derived amide receptor, in conjunction with its Cu (II) and Zn (II) complexes, has been strategically developed to function as remarkably efficient fluorescent receptors with a distinct capability for anion sensing. The comprehensive characterization of the synthesized compounds were achieved through UV-Vis, IR, NMR, and HRMS spectroscopic techniques. Among the Cu (II) and Zn (II) complexes, the latter exhibits superior selectivity for anions, specifically dihydrogen phosphate and hydrogen sulfate, as their tetrabutylammonium salts in a 9:1 acetonitrile-water (v/v) mixture. The Cu (II) complex demonstrates enhanced anion binding compared to the amide ligand, albeit with reduced selectivity. Furthermore, the affinity was evaluated using the Benesi-Hildebrand plot. The binding constants and Limit of Detection (LOD) for both complexes were precisely quantified. The Job plot illustrates a clear 1:1 binding interaction between the metal complexes and the guest anions. Significantly, both metal-complex receptors display a broad spectrum of antibacterial activity, against both gram-positive and gram-negative bacteria. It is worth highlighting that the Zn (II) complexed receptor outperforms the Cu (II) complexed receptor, as evidenced by its considerably lower Minimum Inhibitory Concentration (MIC) value against both bacterial strains.

摘要

一种新型的 8-羟基喹啉衍生酰胺受体,与它的 Cu(II) 和 Zn(II) 配合物一起,被策略性地开发为具有独特阴离子传感能力的高效荧光受体。通过紫外-可见、红外、核磁共振和高分辨率质谱等光谱技术对合成化合物进行了全面表征。在 Cu(II) 和 Zn(II) 配合物中,后者对阴离子,特别是磷酸二氢盐和硫酸氢盐,表现出更高的选择性,作为它们的四丁基铵盐在 9:1 的乙腈-水(v/v)混合物中。Cu(II) 配合物与酰胺配体相比,虽然选择性降低,但对阴离子的结合能力增强。此外,还使用 Benesi-Hildebrand 图评估了亲和力。精确地定量了两个配合物的结合常数和检测限(LOD)。Job 图说明了金属配合物和客体阴离子之间清楚的 1:1 结合相互作用。值得注意的是,两种金属配合物受体都表现出广谱的抗菌活性,对革兰氏阳性菌和革兰氏阴性菌均有效。值得强调的是,Zn(II) 配合物受体的表现优于 Cu(II) 配合物受体,这体现在它对两种细菌菌株的最低抑菌浓度(MIC)值明显更低。

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