RESUMO
A new colorimetric and fluorescent probe was reported, which can be used in a very low dosage (<20 nM) for rapid, highly selective and sensitive detection of biothiols.
Assuntos
Corantes Fluorescentes/química , Imagem Molecular , Compostos de Sulfidrila/análise , Colorimetria , Células HeLa , Humanos , Estrutura MolecularRESUMO
We report a simple and readily available fluorescent probe for rapid, specific, and ratiometric fluorescent detection of the biologically important cysteine (Cys). This probe uses a visible-light excitable excited-state intramolecular proton transfer (ESIPT) dye (4'-dimethylamino-3-hydroxyflavone) as the fluorophore and an acrylate group as the ESIPT blocking agent as well as the recognition unit. Cleavage of the acrylate moiety can be achieved specifically and rapidly by Cys in aqueous solution under mild conditions, which leads to restore the ESIPT process and enables the probe to show a rapid, ratiometric fluorescent detection process for Cys with high selectivity over various analytes, including homocysteine (Hcy) and glutathione (GSH). The detection limit of this probe for Cys was found to be â¼0.2 µM and bioimaging of intracellular Cys by this probe was successfully applied in living cells, indicating that this probe holds great potential for biological applications.
Assuntos
Cisteína/análise , Corantes Fluorescentes/química , Técnicas de Sonda Molecular , Cisteína/química , Corantes Fluorescentes/síntese química , Glutationa/química , Células HeLa , Homocisteína/química , Humanos , Cinética , Espectrometria de FluorescênciaRESUMO
The development of probes for rapid, selective, and sensitive detection of the highly toxic thiophenols is of great importance in both environmental and biological science. Despite the appealing advantages of near-infrared (NIR) fluorescent detection, no NIR fluorescent probes have been reported for thiophenols to date. Using the chemical properties of thiophenols that are able to cleave sulfonamide selectively and efficiently under mild conditions, we herein report a dicyanomethylene-benzopyran (DCMB)-based NIR fluorescent probe for thiophenols. This probe features remarkable large Stokes shift and shows a rapid, highly selective, and sensitive detection process for thiophenols with significant NIR fluorescent turn-on responses. The potential applications of this new NIR fluorescent probe were demonstrated by the quantitative detection of thiophenol in real water samples and by fluorescent imaging of thiophenol in living cells.
Assuntos
Técnicas de Química Analítica/instrumentação , Corantes Fluorescentes/química , Fenóis/análise , Espectroscopia de Luz Próxima ao Infravermelho , Compostos de Sulfidrila/análise , Benzopiranos/química , Água Doce/química , Células HeLa , Humanos , Microscopia de Fluorescência , Nitrilas/químicaRESUMO
We report herein a new approach, which combines fast nucleophilic addition of H2S to an aldehyde group and the subsequent intramolecular thiolysis of dinitrophenyl ether, and can be used to develop efficient and effective H2S probes.