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Near-infrared Fluorescence Probe for Hydrogen Peroxide Detection: Design, Synthesis, and Application in Living Systems

Jiahang Zhang, Liang Shi, Zhao Li, Dongyu Li, Xinwei Tian, Chengxiao Zhang

Analyst. 2019 Jun 7;144(11):3643-3648.

PMID: 31073567

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP91983141 2-(Bromomethyl)phenylboronic acid 2-(Bromomethyl)phenylboronic acid 91983-14-1 Price
LS793369 N-[2-hydroxyethyl]benzamide-3-boronic acid, pinacol ester N-[2-hydroxyethyl]benzamide-3-boronic acid, pinacol ester Price
LS793399 4-(N-cyclopropylsulfonamide)phenylboronic acid pinacol ester 4-(N-cyclopropylsulfonamide)phenylboronic acid pinacol ester Price
LS793437 3-(Tetrahydrofurfurylaminocarbonyl)phenylboronic acid pinacol ester 3-(Tetrahydrofurfurylaminocarbonyl)phenylboronic acid pinacol ester Price
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