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

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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.

Graphical abstract: A distinctive mitochondrion-targeting, in situ-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations in vivo

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Article information


Submitted
18 Nov 2019
Accepted
28 Jan 2020
First published
29 Jan 2020

J. Mater. Chem. B, 2020, Advance Article
Article type
Paper

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

L. Zeng, T. Chen, B. Chen, H. Yuan, R. Sheng and G. Bao, J. Mater. Chem. B, 2020, Advance Article , DOI: 10.1039/C9TB02593F

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