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Issue 4, 2015

A dual-response BODIPY-based fluorescent probe for the discrimination of glutathione from cystein and homocystein

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Abstract

In situ monitoring of intracellular thiol activity in cell growth and function is highly desirable. However, the discriminative detection of glutathione (GSH) from cysteine (Cys) and homocystein (Hcy) and from common amino acids still remains a challenge due to the similar reactivity of the thiol groups in these amino acids. Here we report a novel strategy for selectively sensing GSH by a dual-response mechanism. Integrating two independent reaction sites with a disulfide linker and a thioether function into a fluorescent BODIPY-based chemsensor can guarantee the synergetic dual-response in an elegant fashion to address the discrimination of GSH. In the first synergetic reaction process, the thiol group in GSH, Cys and Hcy induces disulfide cleavage and subsequent intramolecular cyclization to release the unmasked phenol-based BODIPY (discriminating thiol amino acids from other amino acids). In the second synergetic process, upon the substitution of the thioether with the nucleophilic thiolate to form a sulfenyl-BODIPY, only the amino groups of Cys and Hcy, but not that of GSH, undergo a further intramolecular displacement to yield an amino-substituted BODIPY. In this way, we make full use of the kinetically favorable cyclic transition state in the intramolecular rearrangement, and enable photophysical distinction between sulfenyl- and amino-substituted BODIPY for allowing the discriminative detection of GSH over Cys and Hcy and thiol-lacking amino acids under physiological conditions. Moreover, this probe exhibits a distinguishable ratiometric fluorescence pattern generated from the orange imaging channel to the red channel, which proves the differentiation of GSH from Cys and Hcy in living cells.

Graphical abstract: A dual-response BODIPY-based fluorescent probe for the discrimination of glutathione from cystein and homocystein

Supplementary files

Article information


Submitted
20 Jan 2015
Accepted
18 Feb 2015
First published
18 Feb 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 2584-2589
Article type
Edge Article
Author version available

A dual-response BODIPY-based fluorescent probe for the discrimination of glutathione from cystein and homocystein

F. Wang, L. Zhou, C. Zhao, R. Wang, Q. Fei, S. Luo, Z. Guo, H. Tian and W. Zhu, Chem. Sci., 2015, 6, 2584 DOI: 10.1039/C5SC00216H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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