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The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study |
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| Authors: | Olimpo García-Beltrán Natalia MenaEdwin G Pérez Bruce K Cassels Marco T Nuñez Francisca WerlingerDaniel Zavala Margarita E Aliaga Paulina Pavez |
| Institution: | a Department of Chemistry, Faculty of Sciences, University of Chile, Santiago, Chile b Department of Biology, Faculty of Sciences, University of Chile, Santiago, Chile c Institute for Cell Dynamics and Biotechnology, University of Chile, Santiago, Chile d Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andrés Bello, Avenida República 275, Piso 3, Santiago, Chile e Facultad de Química, Pontificia Universidad Católica de Chile, Av. Vicuña Mackenna 4860, Santiago 6094411, Chile |
| Abstract: | Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells. |
| Keywords: | Biothiols Coumarin-based derivatives Fluorescence probes Michael addition |
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