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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 H2O2, 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.

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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 Material and Chemical Characterisation Facility (MC2) 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.

Author information

Correspondence to Steven D. Bull or Tony D. James.

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Odyniec, M.L., Gardiner, J.E., Sedgwick, A.C. et al. Dual enzyme activated fluorescein based fluorescent probe. Front. Chem. Sci. Eng. 14, 117–121 (2020). https://doi.org/10.1007/s11705-018-1785-9

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Keywords

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