Oxidative cleavage-based near-infrared fluorescent probe for hypochlorous acid detection and myeloperoxidase activity evaluation

Abstract

A near-infrared (NIR) fluorescent probe was synthesized and demonstrated to be highly selective in reaction with hypochlorous acid (HOCl), an endogenous reactive oxygen species (ROS) produced by myeloperoxidase in neutrophils. The reaction with HOCl resulted in the NIR fluorescence quenching at 774 nm and the absorbance decreasing at 710 nm, accompanied by the appearance of a new absorption band at 520 nm. The reaction mechanism was carefully examined and proposed to proceed by initial formation of chlorohydrins and subsequent degradation. This NIR fluorescent probe was successfully applied as a selective and sensitive indicator for HOCl on the basis of either colorimetry or fluorometry, which showed detection limits of 0.13 and 0.70 μM, respectively. In addition, the molecular probe was further demonstrated for NIR fluorescence imaging of HOCl in cells and for evaluating the enzymatic activity of myeloperoxidase in the HOCl generation by measuring absorbance change. © 2013 American Chemical Society.