A specific AIE and ESIPT fluorescent probe for peroxynitrite detection and imaging in living cells

Youming Shen; Mengyue Li; Ming Yang; Youyu Zhang; Haitao Li; Xiangyang Zhang

doi:10.1016/j.saa.2019.117230

A specific AIE and ESIPT fluorescent probe for peroxynitrite detection and imaging in living cells

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Nov 5:222:117230. doi: 10.1016/j.saa.2019.117230. Epub 2019 Jun 3.

Authors

Youming Shen¹, Mengyue Li², Ming Yang², Youyu Zhang³, Haitao Li⁴, Xiangyang Zhang²

Affiliations

¹ Hunan Province Cooperative Innovation Center for the Construction & Development of Dongting Lake Ecological Economic Zone, Collaborative Innovation Center for Efficient and Health Production of Fisheries in Hunan Province, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde 415000, PR China; Key Laboratory of Preparation and Application of Environmentally Friendly Materials (Jilin Normal University), Ministry of Education, Changchun 130103, PR China. Electronic address: ymshen79@163.com.
² Hunan Province Cooperative Innovation Center for the Construction & Development of Dongting Lake Ecological Economic Zone, Collaborative Innovation Center for Efficient and Health Production of Fisheries in Hunan Province, College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde 415000, PR China.
³ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China. Electronic address: zhangyy@hunnu.edu.cn.
⁴ Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, PR China.

PMID: 31177001
DOI: 10.1016/j.saa.2019.117230

Abstract

Developing specific and sensitive method for endogenous peroxynitrite (ONOO^-) in living systems is valuable to understand its various pathological events. In this work, a simple and novel fluorescent probe (HPP) based on aggregation induced emission (AIE) as well as excited state intramolecular proton transfer (ESIPT) processes for endogenous ONOO^- detection was constructed containing a diphenylphosphinate as the reactive site and a salicylaldehyde azine as the fluorophore. The probe showed specific fluorescence turn-on response toward ONOO^- owing to the diphenylphosphinate group of HPP reacted with ONOO^-, releasing the salicylaldehyde azine with both AIE and ESIPT characteristics. In addition, the probe exhibited a large Stokes shift, an excellent light-up ratio, high selectivity and excellent sensitivity with a low detection limit of 8 × 10^-8 M for endogenous ONOO^-. Moreover, the probe could be applied to bioimaging of endogenous ONOO^- in live cell, which demonstrated the probe can be used as effective tool for investigation of ONOO^- in biological systems.

Keywords: Aggregation induced emission; Excited state intramolecular proton transfer; Fluorescent sensor; Living cell imaging; ONOO(−).

MeSH terms

Aldehydes / chemistry
Fluorescent Dyes / chemistry*
HeLa Cells
Humans
Limit of Detection
Models, Molecular
Optical Imaging / methods
Peroxynitrous Acid / analysis*
Protons
Spectrometry, Fluorescence / methods

Substances

Aldehydes
Fluorescent Dyes
Protons
Peroxynitrous Acid
salicylaldehyde