Two phenanthroimidazole turn-on probes for the rapid detection of selenocysteine and its application in living cells imaging

Zongcheng Wang; Weikang Su; Huihuang Zheng; Shun Yang; Tingting Yang; Ting Han; Wubliker Dessie; Xingrui He; Yuren Jiang; Yuanqiang Hao

doi:10.1016/j.saa.2021.120585

Two phenanthroimidazole turn-on probes for the rapid detection of selenocysteine and its application in living cells imaging

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Feb 15;267(Pt 2):120585. doi: 10.1016/j.saa.2021.120585. Epub 2021 Nov 6.

Authors

Affiliations

¹ College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China; Hunan Engineering Technology Research Center for Comprehensive Development and Utilization of Biomass Resources, Hunan University of Science and Engineering, Yongzhou 425199, China.
² Hunan Engineering Technology Research Center for Comprehensive Development and Utilization of Biomass Resources, Hunan University of Science and Engineering, Yongzhou 425199, China.
³ College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China.
⁴ College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China. Electronic address: jiangyr@mail.csu.edu.cn.
⁵ Key Laboratory of Theoretical Organic Chemistry and Function Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China. Electronic address: hao0736@163.com.

PMID: 34782266
DOI: 10.1016/j.saa.2021.120585

Abstract

Detection of selenocysteine (Sec) content in cells by fluorescence probe is of great significance for the identification of human related diseases. To achieve fast and sensitive detection of Sec, two isomers A4 and B4 as turn-on fluorescent probes to detect Sec were designed and synthesized. Both A4 and B4 display fast turn-on response, high selectivity and sensitivity toward Sec, which can be applied for fluorescence imaging of Sec in living cells. Compared with B4, A4 has a larger Stokes shift (125 nm), wider pH range (5-10) and lower detection limit (65.4 nM) due to its ESIPT (excited state intramolecular proton transfer) effect. In view of the detection performance of these two probes, they can be used as effective tools for detecting Sec in biological systems.

Keywords: Cell fluorescence imaging; Fluorescence probe; Phenanthroimidazole; Selenocysteine.

MeSH terms

Fluorescent Dyes
HeLa Cells
Humans
Optical Imaging*
Protons
Selenocysteine*

Substances

Fluorescent Dyes
Protons
Selenocysteine