Please wait a minute...
Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

邮发代号 80-969

2019 Impact Factor: 3.552

Frontiers of Chemical Science and Engineering  2020, Vol. 14 Issue (1): 117-121   https://doi.org/10.1007/s11705-018-1785-9
  本期目录
Dual enzyme activated fluorescein based fluorescent probe
Maria L. Odyniec1, Jordan E. Gardiner1, Adam C. Sedgwick1,2, Xiao-Peng He3, Steven D. Bull1(), Tony D. James1()
1. Department of Chemistry, University of Bath, Bath, BA2 7AY, UK
2. Department of Chemistry, University of Texas at Austin, Austin, TX 78712-1224, USA
3. Key Laboratory for Advanced Materials & Feringa Nobel Prize Scientist Joint Research Center, East China University of Science and Technology, Shanghai 200237, China
 全文: PDF(427 KB)   HTML
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.

Key wordschemosensors    dual-activation    GOx    fluorescence    β-glucosidase    molecular logic
收稿日期: 2018-08-15      出版日期: 2020-01-20
Corresponding Author(s): Steven D. Bull,Tony D. James   
 引用本文:   
. [J]. Frontiers of Chemical Science and Engineering, 2020, 14(1): 117-121.
Maria L. Odyniec, Jordan E. Gardiner, Adam C. Sedgwick, Xiao-Peng He, Steven D. Bull, Tony D. James. Dual enzyme activated fluorescein based fluorescent probe. Front. Chem. Sci. Eng., 2020, 14(1): 117-121.
 链接本文:  
https://academic.hep.com.cn/fcse/CN/10.1007/s11705-018-1785-9
https://academic.hep.com.cn/fcse/CN/Y2020/V14/I1/117
Fig.1  
Fig.2  
Fig.3  
Fig.4  
Fig.5  
1 R Medina, G I Owen. Glucose transporters: Expression, regulation and cancer. Journal of Biological Research (Thessaloniki), 2002, 35(1): 9–26
2 C Iadecola. Sugar and Alzheimer’s disease: A bittersweet truth. Nature Neuroscience, 2015, 18(4): 477–478
https://doi.org/10.1038/nn.3986
3 Y An, V R Varma, S Varma, R Casanova, E Dammer, O Pletnikova, C W Chia, J M Egan, L Ferrucci, J Troncoso, A I Levey, J Lah, N T Seyfried, C Legido-Quigley, R O’Brien, M Thambisetty. Evidence for brain glucose dysregulation in Alzheimer’s disease. Alzheimer’s & Dementia, 2018, 14(3): 318–329
https://doi.org/10.1016/j.jalz.2017.09.011
4 H G Körschen, Y Yildiz, D N Raju, S Schonauer, W Bönigk, V Jansen, E Kremmer, U B Kaupp, D Wachten. 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
5 X Zhou, Z Huang, H Yang, Y Jiang, W Wei, Q Li, Q Mo, J Lui. β-Glucosidase inhibtion sensitises breast cancer to chemotherapy. Journal of Biomedicine and Pharmacotherapy, 2017, 91: 504–509
https://doi.org/10.1016/j.biopha.2017.04.113
6 C M Wong, K H Wong, X D Chen. Glucose oxidase: Natural occurrence, function, properties and industrial applications. Applied Microbiology and Biotechnology, 2008, 78(6): 927–938
https://doi.org/10.1007/s00253-008-1407-4
7 A Ramanavicius, N Ryskevic, A Kausaite-Minkstimiene, U Bubniene, I Baleviciute, Y Oztekin, A Ramanaviciene. Fluorescence study of glucose oxidase self-encapsulated within polypyrrole. Sensors and Actuators. B, Chemical, 2012, 171: 753–759
https://doi.org/10.1016/j.snb.2012.05.067
8 J Chan, S C Dodani, C J Chang. Reaction-based small-molecule fluorescent probes for chemoselective bioimaging. Nature Chemistry, 2012, 4(12): 973–984
https://doi.org/10.1038/nchem.1500
9 D Wu, A C Sedgwick, T Gunnlaugsson, E U Akkaya, J Yoon, T D James. Fluorescent chemosensors: The past, present and future. Chemical Society Reviews, 2017, 46(23): 7105–7123
https://doi.org/10.1039/C7CS00240H
10 E P Reeves, H Lu, H L Jacobs, C G M Messina, S Bolsover, G Gabella, E O Potma, A Warley, J Roes, A W Segal. Killing activity of neutrophils is mediated through activation of proteases by K Flux. Nature, 2002, 416(6878): 291–297
https://doi.org/10.1038/416291a
11 C C Winterbourn. Reconciling the chemistry and biology of reactive oxygen species. Nature Chemical Biology, 2008, 4(5): 278–286
https://doi.org/10.1038/nchembio.85
12 N N Wang, C J Miller, P Wang, T D Waite. 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
https://doi.org/10.1016/j.aca.2017.02.033
13 C L Quinlan, I V Perevoschikova, R L S Goncalves, M Hey-Mogensen, M D Brand. The determination and analysis of site-specific rates of mitochondrial reactive oxygen species production. Methods in Enzymology, 2013, 523: 189–217
https://doi.org/10.1016/B978-0-12-405883-5.00012-0
14 K Wannajuk, M Jamkatoke, T Tuntulani, B Tomapatanaget. Highly specific-glucose fluorescence sensing based on boronic anthraquinone derivatives via the GOx enzymatic reaction. Tetrahedron, 2012, 68(43): 8899–8904
https://doi.org/10.1016/j.tet.2012.08.037
15 A C Sedgwick, H H Han, J E Gardiner, S D Bull, X P He, T D James. 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
https://doi.org/10.1039/C8SC00733K
16 B C Dickinson, C Huynh, C J Chang. 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
https://doi.org/10.1021/ja1014103
17 B C Dickinson, C J Chang. 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
https://doi.org/10.1021/ja802355u
18 K H Hong, D I Kim, H Kwon, H J Kim. 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
https://doi.org/10.1039/C3RA42935K
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed