A NIR fluorescent probe based on phenazine with a large Stokes shift for the detection and imaging of endogenous H2O2 in RAW 264.7 cells

Abstract

Hydrogen peroxide (H₂O₂), one of the reactive oxygen species (ROS), plays vital roles in diverse physiological processes. Thus, herein, to improve the signal-to-noise ratio, a new near-infrared region (NIR) fluorophore (PCN) based on reduced phenazine was developed. PCN was further designed as a “turn on” fluorescent probe (PCN-BP) for the detection of H₂O₂ by introducing p-boratebenzyl. After H₂O₂ was added, the p-boratebenzyl group in PCN-BP was oxidized to p-hydroxy benzyl; it then self-departed, forming PCN, which displayed 24-fold NIR emission at 680 nm with a large Stokes shift (more than 200 nm). This probe presented an excellent linear relation with the concentration of H₂O₂ and good selectivity to various ions, ROS and biothiols; thus, it can be utilized as a colorimetric and fluorescence turn-on probe. More importantly, the probe was also employed for the exogenous and endogenous imaging of H₂O₂ in RAW 264.7 cells.