A simple umbelliferone based fluorescent probe for the detection of nitroreductase

Abstract

A simple nitrobenzyl-umbelliferone (NCOU1) was synthesised containing a nitroreductase (NTR) trigger moiety. The presence of NTR, resulted in the fragmentation of the parent molecule and release of the highly emissive fluorophore umbelliferone via an NTR-catalyzed reduction of the nitro group. In the presence of the NTR enzyme, NCOU1 gave rise to a 5-fold increase in fluorescence intensity at 455 nm and was selective for NTR over other reductive enzymes. These results indicate that NCOU1 can be used as a simple assay for the detection of NTR.

Graphical abstract

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Acknowledgements

We would like to thank the EPSRC and the University of Bath for funding. TDJ wishes to thank the Royal Society for a Wolfson Research Merit Award. ACS thanks the EPSRC for his studentship. RBPE acknowledges support funding from Maynooth University. NMR characterisation facilities were provided through the Chemical Characterisation and Analysis Facility (CCAF) at the University of Bath (www.bath.ac.uk/ccaf). All data supporting this study are provided as supplementary information accompanying this paper.

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-017-1697-0 and is accessible for authorized users.

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