Dual enzyme activated fluorescein based fluorescent probe

doi:10.1007/s11705-018-1785-9

Front. Chem. Sci. Eng.

2020, Vol. 14

Issue (1) : 117-121 https://doi.org/10.1007/s11705-018-1785-9

COMMUNICATION

Dual enzyme activated fluorescein based fluorescent probe

Maria L. Odyniec¹, Jordan E. Gardiner¹, Adam C. Sedgwick^1,², 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

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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.

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

Corresponding Author(s): Steven D. Bull,Tony D. James

Online First Date: 01 March 2019 Issue Date: 20 January 2020

Cite this article:

Maria L. Odyniec,Jordan E. Gardiner,Adam C. Sedgwick, et al. Dual enzyme activated fluorescein based fluorescent probe[J]. Front. Chem. Sci. Eng., 2020, 14(1): 117-121.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-018-1785-9
https://academic.hep.com.cn/fcse/EN/Y2020/V14/I1/117

Fig.1 Scheme 1 Structure of PF3-Glc/PF3 and the proposed sensing mechanism for sequential detection of β-glc and H₂O₂

Fig.2 Scheme 2 Synthesis of PF3-Glc

Fig.3 Fluorescence spectra of PF3-Glc (500 nmol/L) with a titration of GOx (1, 2, 4, 6, 8, 10 U, blue lines) in the presence of CelTec2 (0.5 U). Spectra of sensor with GOx (10 U, dotted line) only and CelTec2 (0.5 U, dashed) only are also shown. The spectra were obtained after 1.5 h of incubation with both enzymes. The data was taken in PBS buffer pH= 7.4 (100% H₂O) at 25°C where l_ex = 472 (bandwidth 16 nm)

Fig.4 Emission spectra for PF3-Glc (250 nmol/L) in the presence of CeTec2 (0.5 U) incubated for 30 min at 25°C, prior to addition of H₂O₂ (0.5 mmol/L) which was left to react for a further 60 min. The data was obtained in PBS buffer, pH= 7.3 (100% H₂O w/w) at 25°C, l_ex = 472 (bandwidth 16 nm). The black solid line represents the sensor only. The dotted line represents CeTec2 (0.5 U). The dashed line represents H₂O₂ (0.5 mmol/L)

Fig.5 Selectivity data for PF3-Glc (250 nmol/L). The sensor is incubated with CelTec2 (0.5 U) for 1 h, followed by the addition of ROS. Hydrogen peroxide (0.5 mmol/L) was incubated for 1 hour before measurement. HClO^– (0.5 mmol/L) and ROO^– (0.5 mmol/L) were incubated for 30 minutes before measurement was taken. Singlet oxygen (0.5 mmol/L), superoxide (0.5 mmol/L) and –OH (0.5 mmol/L) were measured immediately after addition. Data shows difference in fluorescence intensity at l = 510 nm after 1 h. The data was taken at pH= 7.3 and25°C.

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