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Issue 11, 2019
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Near-infrared fluorescence probe for hydrogen peroxide detection: design, synthesis, and application in living systems

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Abstract

Using fluorescent probes to detect endogenous hydrogen peroxide, which is associated with many diseases in the human body, remains an essential technique. Cyanine fluorochromes are a class of dyes that have attracted much attention and are widely used in the synthesis of fluorescent probes. In this article, a novel near-infrared (NIR) fluorescence probe for the detection of hydrogen peroxide was constructed and successfully applied to imaging endogenous hydrogen peroxide in vivo. Notably, probe 1 was designed by connecting 4-(bromomethyl)benzeneboronic acid pinacol ester as the sensing unit to the IR-780 hemicyanine skeleton, which exhibits excellent properties like NIR fluorescence emission over 700 nm. Probe 1 has satisfactory sensitivity to hydrogen peroxide with a low detection limit of 0.14 μM (S/N = 3), attributed to a responding mechanism that leads to the oxidation of phenylboronic acid pinacol ester and thereby releases fluorophore 2. Moreover, probe 1 displays excellent selectivity towards hydrogen peroxide over other substances. Taking advantage of these properties, the probe proved to be cell-permeable. Based on the results of N-acetylcysteine and rotenone together, probe 1 is capable of clearly visualizing endogenously produced hydrogen peroxide in living HepG2 cells and mice. The superior performance of the probe, as a reliable chemical tool, makes it of great potential application for exploring the role played by hydrogen peroxide in biological systems.

Graphical abstract: Near-infrared fluorescence probe for hydrogen peroxide detection: design, synthesis, and application in living systems

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Publication details

The article was received on 27 Feb 2019, accepted on 18 Apr 2019 and first published on 25 Apr 2019


Article type: Paper
DOI: 10.1039/C9AN00385A
Analyst, 2019,144, 3643-3648

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    Near-infrared fluorescence probe for hydrogen peroxide detection: design, synthesis, and application in living systems

    J. Zhang, L. Shi, Z. Li, D. Li, X. Tian and C. Zhang, Analyst, 2019, 144, 3643
    DOI: 10.1039/C9AN00385A

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