A turn-on near-infrared fluorescence probe with aggregation-induced emission based on dibenzo[<i>a</i>,<i>c</i>]phenazine for detection of superoxide anions and its application in cell imaging

Abstract

A new turn-on near-infrared fluorescence probe (BDP) based on dibenzo[a,c]phenazine for superoxide anion detection with aggregation-induced emission properties as well as a desirable large Stokes shift was designed and synthesized. After BDP reacted with superoxide, the initial diphenyl-phosphinyl groups of BDP were cleaved, resulting in the production of the pyridinium modified fluorophore (BD) with near-infrared emission. The fluorescent sensor BDP has a high selectivity for superoxide anions over some other intracellular ROSs, reductants, metal ions and amino acids. When HepG2 cells undergo apoptosis and inflammation, BDP is a good probe to keep track of the endogenous superoxide anion level by confocal laser scanning microscopic imaging.