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

A novel dicyanoisophorone-based red-emissive fluorescence probe (YT) with large Stokes shift (230 nm) was synthesized for rapid (<20 s) 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 590 nm to 640 nm 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 5-160 μM concentration range, with the LOD of 4.64 μM. 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.