Amphiphilic silicone-bridged bis-triazoles as effective, selective metal ligands and biologically active agents in lipophilic environment

Publication date: 15 November 2019Source: Journal of Molecular Liquids, Volume 294Author(s): Georgiana-Oana Turcan-Trofin, Mirela-Fernanda Zaltariov, Gheorghe Roman, Sergiu Shova, Nicoleta Vornicu, Mihaela Balan-Porcarasu, Dragos Lucian Isac, Andrei Neamtu, Maria CazacuAbstractPairs of different substituted 3-mercapto-1,2,4-triazole units are coupled, through thioether bridges, to organic-inorganic substrates consisting in short hydrophobic silicone segment. A library of six compounds are isolated as crystalline solids and structurally characterized by X-ray single crystal diffraction, elemental, spectral and thermal analysis. The flexibility of the silicone spacer makes the small molecular compounds exhibit glass transition in the negative domain. The metal binding capacity is evaluated by quantum mechanics calculations, the results being in line with experimental data obtained by UV–vis spectroscopy titration. The results indicate that the prepared compounds can act as ligands for metal ions with high selectivity for Cu2+, an element of interest in biological processes, forming 1:1 stable mononuclear complexes with an association constant up to 8.87 × 103 M−1. The presence of the highly hydrophobic silicone spacer makes the behavior of bis-triazoles obtained more sensitive to the nature of the environment. The preliminary bioassay indicates lipophilic medium more suitable for biocide action of silicone-bridged bis-triazoles, which in some cases far exceeds that o...
Source: Journal of Molecular Liquids - Category: Molecular Biology Source Type: research