Antimicrobial properties of triazolato terpyridine Pd(II) and Pt(II) complexes formed by [3+2] cycloaddition coupling reaction

被引:1
|
作者
Mansour, Ahmed M. [1 ,2 ]
Radacki, Krzysztof [3 ]
Mostafa, Gamal A. E. [4 ]
Ali, Essam A. [4 ]
Shehab, Ola R. [2 ]
机构
[1] United Arab Emirates Univ, Dept Chem, Al Ain, U Arab Emirates
[2] Cairo Univ, Fac Sci, Dept Chem, Gamma St, Cairo 12613, Egypt
[3] Julius Maximilians Univ Wurzburg, Inst Anorgan Chem, D-97074 Wurzburg, Germany
[4] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
基金
英国惠康基金;
关键词
Click reaction; Terpyridine; Lysozyme; Candida albicans; Cryptococcus neoformans; Pd(II) complexes; EFFECTIVE CORE POTENTIALS; MOLECULAR CALCULATIONS; BINDING-AFFINITY; PLATINUM; DNA; CISPLATIN; LYSOZYME; AGENTS; LIGAND; AZIDO;
D O I
10.1016/j.bioorg.2024.107262
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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(N3)L]PF6 (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(triazolatoCF3,COOCH2CH3)L]PF6 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 via the loss of the triazolato ligand. The free ligand and its triazolate complexes displayed selective toxicity against Candida albicans and Cryptococcus neoformans, while no cytotoxicity was observed against the normal human embryonic kidney cell line.
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页数:8
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