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.
References
Medina R, Owen G I. Glucose transporters: Expression, regulation and cancer. Journal of Biological Research (Thessaloniki), 2002, 35(1): 9–26
Iadecola C. Sugar and Alzheimer’s disease: A bittersweet truth. Nature Neuroscience, 2015, 18(4): 477–478
An Y, Varma V R, Varma S, Casanova R, Dammer E, Pletnikova O, Chia C W, Egan J M, Ferrucci L, Troncoso J, Levey A I, Lah J, Seyfried N T, Legido-Quigley C, O’Brien R, Thambisetty M. Evidence for brain glucose dysregulation in Alzheimer’s disease. Alzheimer’s & Dementia, 2018, 14(3): 318–329
Körschen H G, Yildiz Y, Raju D N, Schonauer S, Bönigk W, Jansen V, Kremmer E, Kaupp U B, Wachten D. The non-lysosomal β-glucosidase GBA2 is a non-integral membrane-associated protein at the endoplasmic reticulum (ER) and Golgi. Journal of Biological Chemistry, 2012, 288(5): 12–20
Zhou X, Huang Z, Yang H, Jiang Y, Wei W, Li Q, Mo Q, Lui J. β-Glucosidase inhibtion sensitises breast cancer to chemotherapy. Journal of Biomedicine and Pharmacotherapy, 2017, 91: 504–509
Wong C M, Wong K H, Chen X D. Glucose oxidase: Natural occurrence, function, properties and industrial applications. Applied Microbiology and Biotechnology, 2008, 78(6): 927–938
Ramanavicius A, Ryskevic N, Kausaite-Minkstimiene A, Bubniene U, Baleviciute I, Oztekin Y, Ramanaviciene A. Fluorescence study of glucose oxidase self-encapsulated within polypyrrole. Sensors and Actuators. B, Chemical, 2012, 171: 753–759
Chan J, Dodani S C, Chang C J. Reaction-based small-molecule fluorescent probes for chemoselective bioimaging. Nature Chem-istry, 2012, 4(12): 973–984
Wu D, Sedgwick A C, Gunnlaugsson T, Akkaya E U, Yoon J, James T D. Fluorescent chemosensors: The past, present and future. Chemical Society Reviews, 2017, 46(23): 7105–7123
Reeves E P, Lu H, Jacobs H L, Messina C G M, Bolsover S, Gabella G, Potma E O, Warley A, Roes J, Segal A W. Killing activity of neutrophils is mediated through activation of proteases by K Flux. Nature, 2002, 416(6878): 291–297
Winterbourn C C. Reconciling the chemistry and biology of reactive oxygen species. Nature Chemical Biology, 2008, 4(5): 278–286
Wang N N, Miller C J, Wang P, Waite T D. Quantitative determination of trace hydrogen peroxide in the presence of sulfide using the Amplex Red/horseradish peroxidase assay. Analytica Chimica Acta, 2017, 963: 61–67
Quinlan C L, Perevoschikova I V, Goncalves R L S, Hey-Mogensen M, Brand M D. The determination and analysis of site-specific rates of mitochondrial reactive oxygen species production. Methods in Enzymology, 2013, 523: 189–217
Wannajuk K, Jamkatoke M, Tuntulani T, Tomapatanaget B. Highly specific-glucose fluorescence sensing based on boronic anthraquinone derivatives via the GOx enzymatic reaction. Tetrahedron, 2012, 68(43): 8899–8904
Sedgwick A C, Han H H, Gardiner J E, Bull S D, He X P, James T D. The development of a novel AND logic based fluorescence probe for the detection of peroxynitrite and GSH. Chemical Science (Cambridge), 2018, 9(15): 3672–3676
Dickinson B C, Huynh C, Chang C J. A palette of fluorescent probes with varying emission colours for imaging hydrgoen peroxide signalling in living cells. Journal of the American Chemical Society, 2010, 132(16): 5906–5915
Dickinson B C, Chang C J. A targetable fluorescent probe for imaging hydrogen peroxide in the mitochondria of living cells. Journal of the American Chemical Society, 2008, 130(30): 9638–9639
Hong K H, Kim D I, Kwon H, Kim H J. A fluoresceinylcarbonate-based fluorescent probe for the sensitive detection of biothiols in a HEPES buffer and its cellular expression. RSC Advances, 2014, 4 (2): 978–982
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.
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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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DOI: https://doi.org/10.1007/s11705-018-1785-9
Keywords
- chemosensors
- dual-activation
- GOx
- fluorescence
- β-glucosidase
- molecular logic