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Antimicrobial properties of triazolato terpyridine Pd(II) and Pt(II) complexes formed by [3+2] cycloaddition coupling reaction
Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2024-03-06 , DOI: 10.1016/j.bioorg.2024.107262
Ahmed M. Mansour , Krzysztof Radacki , Gamal A.E. Mostafa , Essam A. Ali , Ola R. Shehab

Modern classes of antimicrobials are crucial because most drugs in development today are basically antibiotic derivatives. Even though a large number of metal-based compounds have been studied as antimicrobial agents, relatively few studies have examined the antimicrobial properties of Pd(II) and Pt(II) compounds. The [3+2] cycloaddition reactions of [M(N)L]PF (M = Pd(II) and Pt(II); L = 4′-(2-pyridyl)-2,2′:6′,2″-terpyridine) with 4,4,4-trifluoro-2-butynoic acid ethyl ester gave the corresponding triazolate complexes. The reaction products were fully characterized with a variety of analytical and spectroscopic tools including X-ray crystallographic analysis. The crystal structure of [Pd(triazolato)L]PF provided cut-off evidence that the kinetically formed N1-triazolato isomer favoured the isomerization to the thermodynamically stable N2-analogue. The experimental work was complemented with computational work to get an insight into the nature of the predominant triazolate isomer. The lysozyme binding affinity of the triazolate complexes was examined by mass spectrometry. An analysis of the lysozyme Pd(II) adducts suggests a coordinative covalent mode of binding the loss of the triazolato ligand. The free ligand and its triazolate complexes displayed selective toxicity against and , while no cytotoxicity was observed against the normal human embryonic kidney cell line.

中文翻译:

[3+2]环加成偶联反应形成的三唑三联吡啶Pd(II)和Pt(II)配合物的抗菌性能

现代类型的抗菌药物至关重要,因为当今开发的大多数药物基本上都是抗生素衍生物。尽管已经研究了大量的金属基化合物作为抗菌剂,但相对较少的研究检验了 Pd(II) 和 Pt(II) 化合物的抗菌特性。 [M(N)L]PF 的 [3+2] 环加成反应 (M = Pd(II) 和 Pt(II); L = 4′-(2-吡啶基)-2,2′:6′,2 '-三联吡啶)与4,4,4-三氟-2-丁炔酸乙酯生成相应的三唑酯络合物。使用包括 X 射线晶体学分析在内的各种分析和光谱工具对反应产物进行了全面表征。 [Pd(三唑基)L]PF 的晶体结构提供了截止证据,表明动力学形成的 N1-三唑基异构体有利于异构化为热力学稳定的 N2-类似物。实验工作辅以计算工作,以深入了解主要三唑酯异构体的性质。通过质谱法检查三唑盐复合物的溶菌酶结合亲和力。对溶菌酶 Pd(II) 加合物的分析表明,结合三唑配体损失的配位共价模式。游离配体及其三唑盐复合物对 和 表现出选择性毒性,而对正常人胚胎肾细胞系没有观察到细胞毒性。
更新日期:2024-03-06
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