(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: Article

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

Huella dactilar

cysteine
Cysteine
Imaging techniques
Sensors
Derivatives
sensors
reactivity
Isoxazoles
Amino acids
Fluorescence
Hardness
amino acids
hardness
selectivity
aqueous solutions
trends
Amino Acids
fluorescence
cells

ASJC Scopus subject areas

  • Instrumentation
  • Materials Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Electrical and Electronic Engineering

Citar esto

De La Torre, Pedro ; García-Beltrán, Olimpo ; Tiznado, William ; Mena, Natalia ; Saavedra, Luis Astudillo ; Cabrera, Margarita Gutiérrez ; Trilleras, Jorge ; Pavez, Paulina ; Aliaga, Margarita E. / (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles as efficient Michael acceptors for cysteine : Real application in biological imaging. En: Sensors and Actuators, B: Chemical. 2014 ; Vol. 193. pp. 391-399.
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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.",
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(E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles as efficient Michael acceptors for cysteine : Real application in biological imaging. / De La Torre, Pedro; García-Beltrán, Olimpo; Tiznado, William; Mena, Natalia; Saavedra, Luis Astudillo; Cabrera, Margarita Gutiérrez; Trilleras, Jorge; Pavez, Paulina; Aliaga, Margarita E.

En: Sensors and Actuators, B: Chemical, Vol. 193, 31.03.2014, p. 391-399.

Resultado de la investigación: Article

TY - JOUR

T1 - (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles as efficient Michael acceptors for cysteine

T2 - Real application in biological imaging

AU - De La Torre, Pedro

AU - García-Beltrán, Olimpo

AU - Tiznado, William

AU - Mena, Natalia

AU - Saavedra, Luis Astudillo

AU - Cabrera, Margarita Gutiérrez

AU - Trilleras, Jorge

AU - Pavez, Paulina

AU - Aliaga, Margarita E.

PY - 2014/3/31

Y1 - 2014/3/31

N2 - (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.

AB - (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.

KW - Acrylonitriles derivatives

KW - Cysteine

KW - Fluorescent sensors

KW - Michael addition

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U2 - 10.1016/j.snb.2013.12.001

DO - 10.1016/j.snb.2013.12.001

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EP - 399

JO - Sensors and Actuators, B: Chemical

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