A NIR fluorescent probe for the selective detection of hydrogen peroxide by acetyl-hydrolyzing in cells

• A near-infrared fluorescent probe was developed for the detection of H 2 O 2 . • The probe had high selectivity and large Stokes shift (128 nm) in respond to H 2 O 2 . • The response mechanism was confirmed by HRMS and DFT calculation. • It was capable of visualizing exogenous and endogenous H 2 O 2 in living cells. Hydrogen peroxide (H 2 O 2 ) is a short-lived, highly reactive oxidant and plays a vital role in biology. Therefore, developing an effective and selective approach for H 2 O 2 detection is very important to better understand it's biological functions. In this paper, a near-infrared fluorescent probe ( YQ-2 ) has been developed for the detection of H 2 O 2 by using an easily synthesized dicyanoisophorone derivative as the near-infrared (NIR) fluorophore and a distinctive acetyl group as the H 2 O 2 recognition group. YQ-2 exhibited high selectivity toward H 2 O 2 with a significant Stokes shift (128 nm). In addition, the recognition mechanism of YQ-2 for H 2 O 2 was confirmed by HRMS and DFT calculation. Inspired by the favorable properties of YQ-2 including NIR emission, high selectivity and low cytotoxicity, YQ-2 was successfully utilized for detecting and imaging exogenous and endogenous H 2 O 2 in living cells with satisfactory results.