The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

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...

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Veröffentlicht in:Tetrahedron letters 2011-12, Vol.52 (49), p.6606-6609
Hauptverfasser: García-Beltrán, Olimpo, Mena, Natalia, Pérez, Edwin G., Cassels, Bruce K., Nuñez, Marco T., Werlinger, Francisca, Zavala, Daniel, Aliaga, Margarita E., Pavez, Paulina
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Sprache:eng
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Zusammenfassung: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.09.137