Dicyanoisophorone-based fluorescent probe with large Stokes shift for ratiometric detection and imaging of exogenous/endogenous hypochlorite in cell and zebrafish.

Abstract

A novel dicyanoisophorone-based red-emissive fluorescence probe (YT) with large Stokes shift (230nm) was synthesized for rapid (<20s) and selective detection of hypochlorite ions in nearly 100% aqueous medium. YT responded to hypochlorite ions via the ClO--promoted oxidative deprotection of thioacetal, leading to a red shift in its fluorescence maximum from 590nm to 640nm accompanied by naked-eye color change from orange to red. The emission response of the probe toward ClO- presented a good linear relationship in the 5-160μM concentration range, with the LOD of 4.64μM. Further, the probe YT was successfully employed in exogenous and LPS-induced endogenous imaging of ClO- in live cells and zebrafish, demonstrating its potential applications in biological science.