A colorimetric and red emissive fluorescent probe for cysteine and its application in bioimaging

作者:Hou Ji Ting; Yang Jin; Li Kun*; Yu Kang Kang; Yu Xiao Qi
来源:Sensors and Actuators B: Chemical , 2015, 214: 92-100.
DOI:10.1016/j.snb.2015.02.112

摘要

Developing effective methods to detect and image Cys in vivo has become an increasingly important area of research. In this work, two colorimetric and fluorescent sensors 1 and 2 were presented for detecting Cys with different reactive rates in an intramolecular cyclization reaction between acrylate and thiols. Probe 2 is the isomer of the probe 1, which has greater steric hindrance than probe 1. The performed reaction kinetics experiments showed that the reaction rates of 1 with thiols were far more rapid than those of 2 with thiols. From the observed crystal structures of these two compounds, we speculate that the larger steric hindrance around the acrylate group in probe 2 outweighs the electronic effect, thus slowing down the reaction between the acrylate and thiols. Probe 1 was successfully applied with negligible cell toxicity toward the imaging of biothiols in living cells and zebrafish.