Metal-Based Antibacterial and Antifungal Agents: Synthesis, Characterization, and In Vitro Biological Evaluation of Co(II), Cu(II), Ni(II), and Zn(II) Complexes With Amino Acid-Derived Compounds.
Metal-Based Antibacterial and Antifungal Agents: Synthesis, Characterization, and In Vitro Biological Evaluation of Co(II), Cu(II), Ni(II), and Zn(II) Complexes With Amino Acid-Derived Compounds.
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DOI：
10.1155/bca/2006/83131
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发表时间：
2006
影响因子：
3.8
通讯作者：
Supuran, Claudiu T.
中科院分区：
文献类型：
--
作者：
Chohan, Zahid H.;Arif, M.;Akhtar, Muhammad A.;Supuran, Claudiu T.
合成了一系列抗菌和抗真菌氨基酸衍生化合物及其钴（II）、铜（II）、镍（II）和锌（II）金属配合物，并通过元素分析、摩尔电导、磁矩、红外光谱和电子光谱测量进行了表征。配体（L1）−（L5）是由β-二酮与甘氨酸、苯丙氨酸、缬氨酸和组氨酸缩合而得，并通过相应氨基酸的甲亚胺-N和去质子化-O对金属离子（钴、铜、镍和锌）起双齿作用。金属离子与配体按摩尔比M：L（1：1）进行化学计量反应，生成[M（L）（H2O）4]Cl型金属配合物（其中M = Co（II）、Cu（II）和Zn（II））和[M（L）2（H2O）2]类型的M：L（1：2）（其中M = Co（II）、Cu（II）、Ni（II）和Zn（II））。磁矩数据表明配合物具有围绕中心金属原子的八面体几何构型。电子光谱数据也支持相同的八面体几何的配合物。配体及其金属配合物的元素分析和NMR光谱数据与它们的结构一致。合成的配体，沿着与它们的金属（II）配合物，筛选它们对四种革兰氏阴性菌的体外抗菌活性（大肠杆菌、福氏志贺菌、铜绿假单胞菌和伤寒沙门氏菌）和两种革兰氏阳性（枯草芽孢杆菌和金黄色葡萄球菌）细菌菌株的体外抗真菌活性和针对长梭毛癣菌、白色念珠菌、黄曲霉、犬小孢子菌、腐皮镰刀菌、和Candida glaberata。这些研究的结果表明，与未络合的配体相比，金属（II）络合物对一种或多种物种更具抗菌/抗真菌性。并进行了卤虫生物测定，以研究其体外细胞毒性。5个化合物（3）、（7）、（10）、（11）和（22）对卤虫显示出较强的细胞毒活性，LD 50分别为8.974 × 10−4、7.022 × 10−4、8.839 × 10−4、7.133 × 10−4和9.725 × 10−4 M/mL。
A series of antibacterial and antifungal amino acid-derived compounds and their cobalt(II), copper(II), nickel(II), and zinc(II) metal complexes have been synthesized and characterized by their elemental analyses, molar conductances, magnetic moments, and IR, and electronic spectral measurements. Ligands (L1)−(L5) were derived by condensation of β-diketones with glycine, phenylalanine, valine, and histidine and act as bidentate towards metal ions (cobalt, copper, nickel, and zinc) via the azomethine-N and deprotonated-O of the respective amino acid. The stoichiometric reaction between the metal(II) ion and synthesized ligands in molar ratio of M : L (1 : 1) resulted in the formation of the metal complexes of type [M(L)(H2O)4]Cl (where M = Co(II), Cu(II), and Zn(II)) and of M : L (1 : 2) of type [M(L)2(H2O)2] (where M = Co(II), Cu(II), Ni(II), and Zn(II)). The magnetic moment data suggested for the complexes to have an octahedral geometry around the central metal atom. The electronic spectral data also supported the same octahedral geometry of the complexes. Elemental analyses and NMR spectral data of the ligands and their metal(II) complexes agree with their proposed structures. The synthesized ligands, along with their metal(II) complexes, were screened for their in vitro antibacterial activity against four Gram-negative (Escherichia coli, Shigella flexeneri, Pseudomonas aeruginosa, and Salmonella typhi) and two Gram-positive (Bacillus subtilis and Staphylococcus aureus) bacterial strains and for in vitro antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani, and Candida glaberata. The results of these studies show the metal(II) complexes to be more antibacterial/antifungal against one or more species as compared to the uncomplexed ligands. The brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties. Five compounds, (3), (7), (10), (11), and (22), displayed potent cytotoxic activity as LD50 = 8.974 × 10−4, 7.022 × 10−4, 8.839 × 10−4, 7.133 × 10−4, and 9.725 × 10−4 M/mL, respectively, against Artemia salina.