TY - JOUR
T1 - (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles as efficient Michael acceptors for cysteine: 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. © 2013 Elsevier B.V.
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. © 2013 Elsevier B.V.
UR - https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84891290692&origin=inward
UR - https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=84891290692&origin=inward
U2 - 10.1016/j.snb.2013.12.001
DO - 10.1016/j.snb.2013.12.001
M3 - Article
SP - 391
EP - 399
JO - Sensors and Actuators, B: Chemical
JF - Sensors and Actuators, B: Chemical
SN - 0925-4005
ER -