A fluorescence turn-on probe for cysteine and homocysteine based on thiol-triggered benzothiazolidine ring formation

Shi-Rong Liu; Chao-Yiu Chang; Shu-Pao Wu

doi:10.1016/j.aca.2014.08.024

A fluorescence turn-on probe for cysteine and homocysteine based on thiol-triggered benzothiazolidine ring formation

Anal Chim Acta. 2014 Nov 7:849:64-9. doi: 10.1016/j.aca.2014.08.024. Epub 2014 Aug 16.

Authors

Shi-Rong Liu¹, Chao-Yiu Chang¹, Shu-Pao Wu²

Affiliations

¹ Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan, ROC.
² Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan, ROC. Electronic address: spwu@mail.nctu.edu.tw.

PMID: 25300219
DOI: 10.1016/j.aca.2014.08.024

Abstract

We synthesized a new coumarin-based probe TP, containing a disulfide moiety, to detect biothiols in cells. A fluorescence turn-on response is induced by the thiol-disulfide exchange of the probe, with subsequent intramolecular benzothiazolidine ring formation giving rise to a fluorescent product. The probe exhibits an excellent selectivity for cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The fluorescent probe also exhibits a highly sensitive fluorescence turn-on response to Cys and Hcy with detection limits of 0.8 μM for Cys and 0.5 μM for Hcy. In addition, confocal fluorescence microscopy imaging using RAW264.7 macrophages demonstrates that the probe TP could be an efficient fluorescent detector for thiols in living cells.

Keywords: Bioimaging; Coumarin; Cysteine; Fluorescent probe; Homocysteine.

Publication types

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

MeSH terms

Animals
Cell Line
Cysteine / analysis*
Fluorescent Dyes / chemistry*
Homocysteine / analysis*
Limit of Detection
Mice
Microscopy, Fluorescence
Optical Imaging
Spectrometry, Fluorescence
Sulfhydryl Compounds / chemistry*
Thiazolidines / chemistry*

Substances

Fluorescent Dyes
Sulfhydryl Compounds
Thiazolidines
Homocysteine
Cysteine