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A simple and easy-to-prepare imidazole-based probe for the selective chromo-fluorogenic recognition of biothiols and Cu(II) in aqueous environments
Dyes and Pigments ( IF 4.5 ) Pub Date : 2018-10-12 , DOI: 10.1016/j.dyepig.2018.10.017
Hazem Essam Okda , Sameh El Sayed , Ismael Otri , Rosa C.M. Ferreira , Susana P.G. Costa , M. Manuela M. Raposo , Ramón Martínez-Máñez , Félix Sancenón

A new simple and easy-to-prepare imidazole-based probe 1 was synthesized and used to detect Cu(II) and biothiols (Cys, Hcy and GSH) in aqueous environments. Addition of increasing amounts of Cu(II) to water (pH 7.4)-acetonitrile 90:10 v/v solutions of probe 1 induced the apperance of a red-shifted absorption together with a marked colour change from colorless to deep blue. In addition, probe 1 was fluorescent and a marked emission quenching in the presence of Cu(II) was observed. The optical response is selective and other cations tested do not induce significant chromo-fluorogenic modulations. Limits of detection for Cu(II) of 0.7 and 3.2 μM using UV–visible and fluorescence data were determined. On the other hand, addition of Cys, Hcy and GSH to the deep-blue water (pH 7.4)-acetonitrile 90:10 v/v solutions of the 1-Cu(II) complex reulted in a marked bleaching together with the appearance of a highly emissive band centred at 475 nm. Other amino acids tested induced negligible response. The limits of detection for Cys, Hcy and GSH using 1-Cu(II) and emission data are 6.5, 5.0 and 10.2 μM, respectively. These optical changes were ascribed to a biothiol-induced demetallation process of the 1-Cu(II) complex that released the free probe. Besides, probe 1 is non-toxic and can be used for Cu(II) detection in HeLa cells.



中文翻译:

一种简单且易于制备的咪唑基探针,用于在水性环境中选择性色谱荧光识别生物硫醇和Cu(II)

合成了一种新的简单易制备的基于咪唑的探针1,并用于检测水性环境中的Cu(II)和生物硫醇(Cys,Hcy和GSH)。向探针1的水(pH 7.4)-乙腈90:10 v / v溶液中添加越来越多的Cu(II)会引起红移吸收的出现,以及从无色到深蓝色的明显颜色变化。另外,探针1呈荧光并且在存在Cu(II)的情况下观察到明显的发射猝灭。光学响应是选择性的,测试的其他阳离子不会引起显着的发色荧光调节。确定了使用紫外可见光和荧光数据检测的Cu(II)的检出限为0.7和3.2μM。另一方面,在1- Cu(II)配合物的深蓝色水(pH 7.4)-乙腈90:10 v / v溶液中添加Cys,Hcy和GSH导致显着的漂白和色相的出现。 475 nm处的高发射带。测试的其他氨基酸诱导的反应可忽略不计。使用1对Cys,Hcy和GSH的检出限-Cu(II)和发射数据分别为6.5、5.0和10.2μM。这些光学变化归因于释放自由探针的1- Cu(II)配合物的生物硫醇诱导的脱金属过程。此外,探针1无毒,可用于HeLa细胞中的Cu(II)检测。

更新日期:2018-10-12
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