(E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles as efficient Michael acceptors for cysteine: Real application in biological imaging

Pedro De La Torre, Olimpo García-Beltrán, William Tiznado, Natalia Mena, Luis Astudillo Saavedra, Margarita Gutiérrez Cabrera, Jorge Trilleras, Paulina Pavez, Margarita E. Aliaga

Resultado de la investigación: Contribución a una revistaArtículo

9 Citas (Scopus)

Resumen

(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.

Idioma originalInglés
Páginas (desde-hasta)391-399
Número de páginas9
PublicaciónSensors and Actuators, B: Chemical
Volumen193
DOI
EstadoPublicada - 31 mar 2014

Áreas temáticas de ASJC Scopus

  • Instrumental
  • Química de los materiales
  • Superficies, recubrimientos y láminas
  • Metales y aleaciones
  • Materiales electrónicos, ópticos y magnéticos
  • Física de la materia condensada
  • Ingeniería eléctrica y electrónica

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