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

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,...

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Veröffentlicht in:Journal of materials chemistry. B, Materials for biology and medicine Materials for biology and medicine, 2020-03, Vol.8 (9), p.1914-1921
Hauptverfasser: Zeng, Lintao, Chen, Tianhong, Chen, Bao-Quan, Yuan, Hou-Qun, Sheng, Ruilong, Bao, Guang-Ming
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container_end_page 1921
container_issue 9
container_start_page 1914
container_title Journal of materials chemistry. B, Materials for biology and medicine
container_volume 8
creator Zeng, Lintao
Chen, Tianhong
Chen, Bao-Quan
Yuan, Hou-Qun
Sheng, Ruilong
Bao, Guang-Ming
description 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.
doi_str_mv 10.1039/c9tb02593f
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ispartof Journal of materials chemistry. B, Materials for biology and medicine, 2020-03, Vol.8 (9), p.1914-1921
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source MEDLINE; Royal Society Of Chemistry Journals 2008-
subjects Animals
Breast cancer
Derivatives
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Fluorescent indicators
Humans
I.R. radiation
Infrared Rays
Malononitrile
MCF-7 Cells
Mitochondria
Mitochondria - chemistry
Molecular Structure
Optical Imaging
Sulfur
Sulfur dioxide
Sulfur Dioxide - analysis
Tumor Cells, Cultured
Variation
Zebrafish
title 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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