A distinctive mitochondrion-targeting, <i>in situ</i>-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations <i>in vivo</i>

Abstract

Sulfur dioxide derivatives are intimately involved in some physiological processes in organisms, and high levels of these substances can cause many diseases. Herein, we rationally prepared a mitochondrion-targeting, in situ-activatable near-infrared (NIR) fluorescent probe (DCQN) by coupling 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile with 3-quinolinium carboxaldehyde. DCQN displayed a NIR fluorescence turn-on signal to indicate the presence of HSO3-, along with a considerable hyperchromic shift from light yellow to purple via a 1,4-nucleophilic addition reaction. We were able to use DCQN to instantaneously and quantitatively determine the concentration of HSO3- with high specificity, a low detection limit (24 nM), a large Stokes shift (∼110 nm), and a high contrast ratio. Moreover, DCQN displayed good mitochondrion-targeting abilities and was in situ-activated by HSO3- to produce NIR fluorescence for imaging HSO3- in the mitochondria of live breast cancer cells. Furthermore, DCQN was used to monitor HSO3- in zebrafish with a high contrast ratio.