Issue 15, 2018

The development of a novel AND logic based fluorescence probe for the detection of peroxynitrite and GSH

Abstract

We have developed a novel AND logic based fluorescence probe for the simultaneous detection of ONOO and GSH (GSH-PF3). The GSH-PF3 probe was synthesised over three steps starting from commercially available fluorescein. The probe was constructed by attaching the GSH reactive motif, 2,4-dinitrobenzenesulfonyl, to the previously reported boronate fluorescence based probe, PF3. GSH-PF3 produced only a small fluorescence response towards the addition of GSH or ONOO separately. However, when the probe was exposed to both analytes, there was a significant (40-fold) fluorescence enhancement. GSH-PF3 demonstrated an excellent selectivity towards both GSH and ONOO. In cellular imaging experiments the probe was shown to be cell permeable with no ‘turn-on’ response observed for the addition of either GSH or ONOO separately. However, in the presence of both analytes, a clear fluorescence response was observed in live cells. GSH-PF3 was further able to monitor the co-existence of metabolically produced ONOO and GSH by exogenous stimulation.

Graphical abstract: The development of a novel AND logic based fluorescence probe for the detection of peroxynitrite and GSH

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Feb 2018
Accepted
10 Mar 2018
First published
16 Mar 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 3672-3676

The development of a novel AND logic based fluorescence probe for the detection of peroxynitrite and GSH

A. C. Sedgwick, H. Han, J. E. Gardiner, S. D. Bull, X. He and T. D. James, Chem. Sci., 2018, 9, 3672 DOI: 10.1039/C8SC00733K

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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