Highly selective and sensitive benzopyran-based fluorescent probes for imaging exogenous and endogenous peroxynitrite

Jun Wang; Shu-Yang Liu; Guan-Hua Yu; Hao-Ran Hu; Ying Fang; Shao-Jin Chen; Kun-Peng Wang; Zhi-Qiang Hu

doi:10.1016/j.saa.2023.122747

Highly selective and sensitive benzopyran-based fluorescent probes for imaging exogenous and endogenous peroxynitrite

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Sep 5:297:122747. doi: 10.1016/j.saa.2023.122747. Epub 2023 Apr 14.

Authors

Jun Wang¹, Shu-Yang Liu¹, Guan-Hua Yu¹, Hao-Ran Hu¹, Ying Fang², Shao-Jin Chen¹, Kun-Peng Wang³, Zhi-Qiang Hu⁴

Affiliations

¹ Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
² Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China. Electronic address: fangyingqust@126.com.
³ Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China. Electronic address: wangkunpeng@qust.edu.cn.
⁴ Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China. Electronic address: huzhiqiang@qust.edu.cn.

PMID: 37080056
DOI: 10.1016/j.saa.2023.122747

Abstract

Peroxynitrite is widely present in organisms and closely related to many pathophysiological functions. Therefore, it is of great physiological significance to develop capable probes for detecting ONOO^-. In this work, a novel fluorescent probe B-Ch was designed based on the intramolecular charge transfer (ICT) effect. By means of molecular engineering, the replacement from diethylamine group to hydroxyl group has improved the detection sensitivity of the probe. After the addition of ONOO^-, the solution color and fluorescence showed noticeable changes, which were visible to the naked eye. The probe showed excellent advantages: visualization, good selectivity, low sensitivity (22.4 nM), good stability and biocompatibility, exogenous and endogenous imaging of ONOO^- in HeLa cells.

Keywords: Benzopyran; Cell imaging; Dicyano-vinyl; Fluorescent probe; Peroxynitrite.

MeSH terms

Benzopyrans
Diagnostic Imaging
Fluorescent Dyes*
HeLa Cells
Humans
Optical Imaging
Peroxynitrous Acid*

Substances

Fluorescent Dyes
Peroxynitrous Acid
Benzopyrans