Dual enzyme activated fluorescein based fluorescent probe

Abstract

A simple dual analyte fluorescein-based probe (PF3-Glc) was synthesised containing β-glucosidase (β-glc) and hydrogen peroxide (H₂O₂) trigger units. The presence of β-glc, resulted in fragmentation of the parent molecule releasing glucose and the slightly fluorescent mono-boronate fluorescein (PF3). Subsequently, in the presence of glucose oxidase (GOx), the released glucose was catalytically converted to D-glucono-δ-lactone, which produced H₂O₂ as a by-product. The GOx-produced H₂O_2, resulted in classic H₂O₂-mediated boronate oxidation and the release of the highly emissive fluorophore, fluorescein. This unique cascade reaction lead to an 80-fold increase in fluorescence intensity.

Graphical abstract

Keywords

chemosensors / dual-activation / GOx / fluorescence / β-glucosidase / molecular logic

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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. MLO, JEG and ACS thank the EPSRC for their studentships. NMR and MS Characterisation facilities were provided through the Chemical Characterisation and Analysis Facility (CCAF) at the University of Bath. The EPSRC UK National Mass Spectrometry Facility at Swansea University is thanked for analyses. 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/s11705-018-1785-9 and is accessible for authorized users.

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RIGHTS & PERMISSIONS

2019 The Author(s) 2019. This article is published with open access at link.springer.com and journal.hep.com.cn 2019