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Synthesis, characterization and antibacterial activity of metalloporphyrins: Role of central metal ion
Results in Chemistry Pub Date : 2020-10-13 , DOI: 10.1016/j.rechem.2020.100073
Belete B. Beyene , Ayenew M. Mihirteu , Misganaw T. Ayana , Amogne W. Yibeltal

Modification of synthetic porphyrins is one of the promising strategies in an attempt to get molecules with desired properties and applications. Here in we report synthesis, photophysical characterization and antibacterial activity of 5, 10, 15, 20-tetrakis-(4- methoxy carbonyl phenyl) porphyrin M(II); where M = Co, Fe, Ni, Zn. Metallation of the ligand was confirmed by using UV–Vis spectroscopy and ESI-Ms measurement, in which the number of Q bands in absorption spectra of the ligand decreased from four to one or two as a result of metal insertion to the porphyrin core. The antibacterial activity study of the complexes toward two Gram-positive (Staphylococcus aureus (S. aureus) and Streptococcus pyogenes (s. pyogenes)) and two Gram-negative (Escherichia coli (E. coli) and Klebsiella pneumoniae (K. pneumoniae)) bacteria by disc diffusion method showed a promising inhibitory activity. The complexes exhibited highest activities at highest concentration and are better than the activity of free base ligand, the salts and blank solution. This could be explained on the basis of Overton's concept of cell permeability and Tweed's Chelation theory. An increased lipo-solubility enhances the penetration of the complexes in to the lipid membrane and interferes in the normal activities of the bacteria. Our study, therefore, showed that the growth inhibitory effect of these metalloporphyrins is generally in order of ZnTPPCOOMe > NiTPPCOOMe > CoTPPCOOMe> FeTPPCOOMe, which may be attributed to the better lipophilicity and binding of the complex with the cellular components.



中文翻译:

金属卟啉的合成,表征和抗菌活性:中心金属离子的作用

合成卟啉的修饰是试图获得具有所需性质和应用的分子的有前途的策略之一。在这里我们报告5、10、15、20-四-(4-甲氧基羰基苯基)卟啉M(II)的合成,光物理特性和抗菌活性;其中M = Co,Fe,Ni,Zn。通过UV-Vis光谱和ESI-Ms测量证实了配体的金属化,其中由于金属插入到卟啉核中,配体吸收光谱中的Q带数量从4个减少到1个或2个。走向两个革兰氏阳性的复合物的抗菌活性的研究(金黄色葡萄球菌小号金黄色葡萄球菌)和化脓性链球菌(一个或多个。酿脓))和两个革兰氏阴性(大肠杆菌Ë大肠杆菌)和肺炎克雷伯氏菌(K. pneumoniae)细菌通过圆盘扩散法显示出有希望的抑制活性。该复合物在最高浓度下表现出最高的活性,并且优于游离碱配体,盐和空白溶液的活性。这可以根据Overton的细胞渗透性概念和Tweed的螯合理论来解释。脂溶性的增加增强了复合物对脂质膜的渗透,并干扰了细菌的正常活动。因此,我们的研究表明,这些金属卟啉的生长抑制作用通常按ZnTPPCOOMe> NiTPPCOOMe> CoTPPCOOMe> FeTPPCOOMe的顺序排列,这可能归因于更好的亲脂性和复合物与细胞组分的结合。

更新日期:2020-11-03
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