Dual enzyme activated fluorescein based fluorescent probe

Maria L. Odyniec; Jordan E. Gardiner; Adam C. Sedgwick; Xiao Peng He; Steven D. Bull; Tony D. James

doi:10.1007/s11705-018-1785-9

Dual enzyme activated fluorescein based fluorescent probe

Maria L. Odyniec, Jordan E. Gardiner, Adam C. Sedgwick, Xiao Peng He, Steven D. Bull, Tony D. James

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

13 Citations (SciVal)

Abstract

A simple dual analyte fluorescein-based probe (PF3-Glc) was synthesised containing β-glucosidase (β-glc) and hydrogen peroxide (H ₂ O ₂ ) 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 H ₂ O ₂ as a by-product. The GOx-produced H ₂ O ₂ , resulted in classic H ₂ O ₂ -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.[Figure not available: see fulltext.].

Original language	English
Pages (from-to)	117–121
Journal	Frontiers of Chemical Science and Engineering
Volume	14
Early online date	1 Mar 2019
DOIs	https://doi.org/10.1007/s11705-018-1785-9
Publication status	Published - 1 Feb 2020

Keywords

chemosensors
dual-activation
fluorescence
GOx
molecular logic
β-glucosidase

ASJC Scopus subject areas

General Chemical Engineering

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10.1007/s11705-018-1785-9Licence: CC BY

Cite this

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title = "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 (H 2 O 2 ) 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 H 2 O 2 as a by-product. The GOx-produced H 2 O 2 , resulted in classic H 2 O 2 -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.[Figure not available: see fulltext.]. ",

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T1 - Dual enzyme activated fluorescein based fluorescent probe

AU - Odyniec, Maria L.

AU - Gardiner, Jordan E.

AU - Sedgwick, Adam C.

AU - He, Xiao Peng

AU - Bull, Steven D.

AU - James, Tony D.

PY - 2020/2/1

Y1 - 2020/2/1

N2 - A simple dual analyte fluorescein-based probe (PF3-Glc) was synthesised containing β-glucosidase (β-glc) and hydrogen peroxide (H 2 O 2 ) 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 H 2 O 2 as a by-product. The GOx-produced H 2 O 2 , resulted in classic H 2 O 2 -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.[Figure not available: see fulltext.].

AB - A simple dual analyte fluorescein-based probe (PF3-Glc) was synthesised containing β-glucosidase (β-glc) and hydrogen peroxide (H 2 O 2 ) 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 H 2 O 2 as a by-product. The GOx-produced H 2 O 2 , resulted in classic H 2 O 2 -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.[Figure not available: see fulltext.].

KW - chemosensors

KW - dual-activation

KW - fluorescence

KW - GOx

KW - molecular logic

KW - β-glucosidase

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Dual enzyme activated fluorescein based fluorescent probe

Abstract

Keywords

ASJC Scopus subject areas

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