A nitrobenzoxadiazole-based near-infrared fluorescent probe for the specific imaging of H2S in inflammatory and tumor mice

Wen-Xin Wang; Zhi-Qing Wang; Zhi-Ke Tan; Guo-Jiang Mao; Dong-Hua Chen; Chun-Yan Li

doi:10.1039/D2AN00623E

A nitrobenzoxadiazole-based near-infrared fluorescent probe for the specific imaging of H₂S in inflammatory and tumor mice†

Wen-Xin Wang,^a Zhi-Qing Wang,^a Zhi-Ke Tan,^a Guo-Jiang Mao,^b Dong-Hua Chen^a and Chun-Yan Li

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, PR China
E-mail: lichunyan79@sina.com

^b Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, PR China

Abstract

As a common gaseous signaling molecule, hydrogen sulfide (H₂S) plays a vital role in physiology and pathology. The development of fluorescent probes for detecting H₂S has attracted widespread attention. However, most of the reported fluorescent probes with nitrobenzoxadiazole (NBD) as the recognition group have been widely used to simultaneously detect biothiols and H₂S, instead of specifically detecting H₂S. Herein, a novel NBD-based near-infrared (NIR) fluorescent probe named CX-N for the detection of H₂S is synthesized. The selectivity of CX-N for H₂S is significantly higher than that for biothiols and other potential interferences. After reacting with H₂S, CX-N shows a significant increase in NIR fluorescence (75-fold), large Stokes shift (155 nm) and fast response (4 min). And the possible response mechanism of CX-N to H₂S is given and confirmed by HPLC and HRMS. Based on the low cytotoxicity of CX-N, it has been used for H₂S imaging in live cells and zebrafish. More importantly, CX-N has also been successfully applied for the real-time imaging of H₂S in inflammatory and tumor mice based on its NIR emission, which provides a reliable platform for the specific recognition of H₂S in complex biological systems.

This article is part of the themed collection: Analyst HOT Articles 2022

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Article information

DOI: https://doi.org/10.1039/D2AN00623E
Article type: Paper
Submitted: 09 Apr 2022
Accepted: 01 May 2022
First published: 30 May 2022

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Analyst, 2022,147, 2712-2717

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A nitrobenzoxadiazole-based near-infrared fluorescent probe for the specific imaging of H₂S in inflammatory and tumor mice

W. Wang, Z. Wang, Z. Tan, G. Mao, D. Chen and C. Li, Analyst, 2022, 147, 2712 DOI: 10.1039/D2AN00623E

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