Reaction-based fluorescent probe for detection of endogenous cyanide in real biological samples.

Abstract

Herein, two compounds (1 a and 1 b) were rationally constructed as novel reaction-based fluorescent probes for CN(-) by making use of the electron-withdrawing ability of the cyano group that was formed from the sensing reaction. Notably, this design strategy was first employed for the development of fluorescent CN(-) probes. The experimental details showed that probe 1 a exhibited a fluorescence turn-on response to CN(-), whereas other anions, biological thiols, and hydrogen sulfide gave almost no interference. The detection limit of probe 1 a for CN(-) was found to be 0.12 μM. The sensing reaction product of 1 a with CN(-) was characterized by NMR spectroscopy and mass spectrometry. TD-DFT calculations demonstrated that the formed cyano group drives the intramolecular charge transfer (ICT) process from coumarin dye to the cyano group and thus the original strong ICT from the coumarin dye to the 3-position pyridyl vinyl ketone substituent is weakened, which results in recovery of coumarin fluorescence. The practical utility of 1 a was also examined. By fabricating paper strips, probe 1 a can be used as a simple tool to detect CN(-) in field measurements. Moreover, probe 1 a has been successfully applied for quantitative detection of endogenous CN(-) from cassava root.