Near-infrared fluorescence probe with a large Stokes shift for selectively imaging of hydrogen peroxide in living cells and in vivo

In this work, we have designed and synthesized a large stokes shift and near-infrared (NIR) probe DCM-HNU for visualization of H 2 O 2 in both living HeLa cells and zebra fish. The probe DCM-HNU was structured based on phenylborate pincinol ester as the recognition group connecting DCM-OH via nucleophilic substitution reaction . The probe possessed large stokes shift (205 nm), near-infrared (NIR) emission (658 nm). 0.17 μM detection Limit, 10,550 L·mol −1 cm −1 molar extinction coefficient , 2.06 × 10 −3 S −1 reaction rate constant, and excellent selectivity proved the condition for practical application. There was a good linear relationship between fluorescence intensity and H 2 O 2 concentration from 0 to 200 μM (R 2 = 0.9955) to facilitate quantitative analysis of H 2 O 2 . More importantly, the probe is able to visualize exogenous and endogenous H 2 O 2 in living HeLa cells and zebra fish. The superior properties of the probe provide potential for exploring the function and participation of H 2 O 2 in biological systems. • Large stokes shift (205 nm), near-infrared (NIR) emission (658 nm). • The probe is able to visualize exogenous and endogenous H 2 O 2 .