(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

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

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 languageEnglish
Pages (from-to)391-399
Number of pages9
JournalSensors and Actuators, B: Chemical
Volume193
DOIs
Publication statusPublished - 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

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