A colorimetric and fluorescent probe for detecting intracellular GSH

Chunyang Chen; Wei Liu; Cong Xu; Weisheng Liu

doi:10.1016/j.bios.2015.04.016

A colorimetric and fluorescent probe for detecting intracellular GSH

Biosens Bioelectron. 2015 Sep 15:71:68-74. doi: 10.1016/j.bios.2015.04.016. Epub 2015 Apr 8.

Authors

Chunyang Chen¹, Wei Liu¹, Cong Xu¹, Weisheng Liu²

Affiliations

¹ Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
² Key Laboratory of Nonferrous Metals Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China. Electronic address: liuws@lzu.edu.cn.

PMID: 25889346
DOI: 10.1016/j.bios.2015.04.016

Abstract

A new rapid and highly sensitive coumarin-based probe (probe 1) has been designed and synthesized for detecting intracellular GSH. Probe 1 was prepared from 4-methylumbelliferone using a 3-step procedure. It was converted into a latent fluorescence probe, which allowed it to achieve high sensitivity (LOD 122 nM) and fluorescence turn-on response (F/F0>15) toward GSH over other various natural amino acids in PBS buffer solution at pH 7.4. Owing to a specific Michael addition between thiols and the double bond of nitroolefin moiety, probe 1 displayed a high selectivity toward GSH. Afterwards, probe 1 was successfully used for fluorescence imaging of GSH in Hela and Hek-293a cells, and a rapid response was observed in the Hek-293a cells after incubating with probe 1 for 1 min. Simultaneously, a quantitative determination was achieved in Hela cells in the range of 8-48 μM. Specific fluorescence imaging of plants tissue was obtained for proving the permeability of probe 1. Finally, the viability was measured to be more than 80%, which shows probe 1 can serve as a rapid and biocompatible probe for GSH in cells.

Keywords: Bioimaging; Colorimetric; Coumarin; Fluorescent; Glutathione; Probe.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biosensing Techniques / methods*
Cell Survival
Colorimetry / methods*
Coumarins / chemical synthesis
Coumarins / chemistry*
Fluorescent Dyes / chemical synthesis
Fluorescent Dyes / chemistry*
Glutathione / analysis*
HEK293 Cells
HeLa Cells
Humans
Optical Imaging / methods*
Spectrometry, Fluorescence / methods

Substances

Coumarins
Fluorescent Dyes
coumarin
Glutathione