A near-infrared ratiometric fluorescent probe for hydrazine and its application for gaseous sensing and cell imaging

Lijie Luo; Jiayuan Cheng; Shu Chen; Peisheng Zhang; Song Chen; Zilong Tang; Rongjin Zeng; Maotian Xu; Yuanqiang Hao

doi:10.1016/j.saa.2023.122692

A near-infrared ratiometric fluorescent probe for hydrazine and its application for gaseous sensing and cell imaging

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Aug 5:296:122692. doi: 10.1016/j.saa.2023.122692. Epub 2023 Mar 31.

Authors

Lijie Luo¹, Jiayuan Cheng¹, Shu Chen², Peisheng Zhang¹, Song Chen³, Zilong Tang¹, Rongjin Zeng¹, Maotian Xu⁴, Yuanqiang Hao⁵

Affiliations

¹ Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
² Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China. Electronic address: chenshu@hnust.edu.cn.
³ Key Laboratory of Hunan Province for Water Environment and Agriculture Product Safety, Central South University, Changsha 410083, China; College of Pharmacy, Qiqihar Medical University, Qiqihar 161006, China.
⁴ Henan Key Laboratory of Biomolecular Recognition and Sensing, Henan Joint International Research Laboratory of Chemo/Biosensing and Early Diagnosis of Major Diseases, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China.
⁵ Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China; Henan Key Laboratory of Biomolecular Recognition and Sensing, Henan Joint International Research Laboratory of Chemo/Biosensing and Early Diagnosis of Major Diseases, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China. Electronic address: hao0736@163.com.

PMID: 37023655
DOI: 10.1016/j.saa.2023.122692

Abstract

Hydrazine (N₂H₄) is a widely used raw material in the chemical industry, but at the same time hydrazine has extremely high toxicity. Therefore, the development of efficient detection methods is crucial for monitoring hydrazine in the environment and evaluating the biological toxicity of hydrazine. This study reports a near-infrared ratiometric fluorescent probe (DCPBCl₂-Hz) for the detection of hydrazine by coupling a chlorine-substituted D-π-A fluorophore (DCPBCl₂) to the recognition group acetyl. Due to the halogen effect of chlorine substitution, the fluorophore has an elevated fluorescence efficiency and a lowered pKa value and is suitable for physiological pH conditions. Hydrazine can specifically react with the acetyl group of the fluorescent probe to release the fluorophore DCPBCl₂, so the fluorescence emission of the probe system significantly shifted from 490 nm to 660 nm. The fluorescent probe has many advantages, such as good selectivity, high sensitivity, large Stokes shift, and wide applicable pH range. The probe-loaded silica plates can realize convenient sensing gaseous hydrazine with content down to 1 ppm (mg/m³). Subsequently, DCPBCl₂-Hz was successfully applied to detect hydrazine in soils. In addition, the probe can also penetrate living cells and allow the visualization of intracellular hydrazine. It can be anticipated that probe DCPBCl₂-Hz will be a useful tool for sensing hydrazine in biological and environmental applications.

Keywords: Cell imaging; Fluorescent probe; Gaseous sensing; Halogen effects; Hydrazine.

MeSH terms

Chlorine
Fluorescent Dyes* / chemistry
Gases*
HeLa Cells
Humans
Hydrazines / chemistry
Spectrometry, Fluorescence

Substances

Fluorescent Dyes
Gases
Chlorine
Hydrazines