Abstract
(E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles derivatives (compounds 1, 2, and 3) were synthesized and assessed for their ability to recognize cysteine (Cys) in aqueous solution via a Michael-type reaction. The sensors can be used for the quantification of Cys with detection limits of ca. 10-5 M. The sensors showed excellent selectivity for Cys over other amino acids. The most reactive five-membered heterocyclic substituent in the tested compounds was the isoxazole derivative (compound 2). The reactivity study was complemented with a theoretical analysis based on the global electrophilicity and hardness. Interestingly, both descriptors correctly assign the reactivity trend 2 > 1 ≈ 3, in accordance with the experimental evidence. Finally, these sensors were successfully applied to the fluorescence imaging of intracellular Cys in SH-SY5Y cells.
Original language | English |
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Pages (from-to) | 391-399 |
Number of pages | 9 |
Journal | Sensors and Actuators, B: Chemical |
Volume | 193 |
DOIs | |
Publication status | Published - 31 Mar 2014 |
Keywords
- Acrylonitriles derivatives
- Cysteine
- Fluorescent sensors
- Michael addition
ASJC Scopus subject areas
- Electronic, Optical and Magnetic Materials
- Instrumentation
- Condensed Matter Physics
- Surfaces, Coatings and Films
- Metals and Alloys
- Electrical and Electronic Engineering
- Materials Chemistry