Coumarin-based fluorescent probe for the detection of glutathione and nitroreductase

Xue Tian; Lokesh K. Kumawat; Steven D. Bull; Robert B. P. Elmes; Luling Wu; Tony D. James

doi:10.1016/j.tet.2020.131890

Coumarin-based fluorescent probe for the detection of glutathione and nitroreductase

Xue Tian, Lokesh K. Kumawat, Steven D. Bull, Robert B. P. Elmes, Luling Wu, Tony D. James

Maynooth University

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Abstract

With this research we set out to develop a coumarin-based novel fluorescent probe NTR-AHC for the detection of biological thiols and nitroreductase (NTR). Probe NTR-AHC was constructed by attaching the NTR trigger moiety (p-nitrobenzyl) and biothiol acceptor (maleic acid monoamide), to the core fluorophore AHC. In the presence of both glutathione (GSH) and NTR, probe NTR-AHC produced a >8-fold increase in fluorescence intensity at 463 nm.

Original language	English
Article number	131890
Journal	Tetrahedron
Volume	82
Early online date	28 Dec 2020
DOIs	https://doi.org/10.1016/j.tet.2020.131890
Publication status	Published - 26 Feb 2021

Funding

XT wishes to thank the University of Bath for supporting her PhD in the UK. LKK wishes to acknowledge the Irish Research Council for a Government of Ireland Postdoctoral Research Fellowship ( GOIPD/2017/1091 ) and Science Foundation Ireland are acknowledged for the funding of Advion Mass Spec facilities through the Opportunistic Infrastructure Fund ( 16/RI/3399 ). RBPE would like to thank Science Foundation Ireland ( SFI ) and the European Regional Development Fund ( 12/RC/2275_P2 ). LW wishes to thank China Scholarship Council and the University of Bath for supporting his PhD in the UK. 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 and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support ( 2020ZD01 ). NMR characterisation facilities were provided by the Material and Chemical Characterisation Facility (MC 2 ) at the University of Bath ( http://go.bath.ac.uk/mc2 ). The EPSRC UK National Mass Spectrometry Facility at Swansea University is thanked for analyses. All data supporting this study are provided as ESI† accompanying this paper. XT wishes to thank the University of Bath for supporting her PhD in the UK. LKK wishes to acknowledge the Irish Research Council for a Government of Ireland Postdoctoral Research Fellowship (GOIPD/2017/1091) and Science Foundation Ireland are acknowledged for the funding of Advion Mass Spec facilities through the Opportunistic Infrastructure Fund (16/RI/3399). RBPE would like to thank Science Foundation Ireland (SFI) and the European Regional Development Fund (12/RC/2275_P2). LW wishes to thank China Scholarship Council and the University of Bath for supporting his PhD in the UK. 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 and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01). NMR characterisation facilities were provided by the Material and Chemical Characterisation Facility (MC2) at the University of Bath (http://go.bath.ac.uk/mc2). The EPSRC UK National Mass Spectrometry Facility at Swansea University is thanked for analyses. All data supporting this study are provided as ESI? accompanying this paper.

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10.1016/j.tet.2020.131890

Tetrahedron manuscript 24012021.PDFAccepted author manuscript, 557 KBLicence: CC BY-NC-ND

https://linkinghub.elsevier.com/retrieve/pii/S0040402020311546

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)
Material and Chemical Characterisation (MC2)
Facility/equipment: Equipment

Cite this

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title = "Coumarin-based fluorescent probe for the detection of glutathione and nitroreductase",

abstract = "With this research we set out to develop a coumarin-based novel fluorescent probe NTR-AHC for the detection of biological thiols and nitroreductase (NTR). Probe NTR-AHC was constructed by attaching the NTR trigger moiety (p-nitrobenzyl) and biothiol acceptor (maleic acid monoamide), to the core fluorophore AHC. In the presence of both glutathione (GSH) and NTR, probe NTR-AHC produced a >8-fold increase in fluorescence intensity at 463 nm.",

author = "Xue Tian and Kumawat, {Lokesh K.} and Bull, {Steven D.} and Elmes, {Robert B. P.} and Luling Wu and James, {Tony D.}",

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AU - Tian, Xue

AU - Kumawat, Lokesh K.

AU - Bull, Steven D.

AU - Elmes, Robert B. P.

AU - Wu, Luling

AU - James, Tony D.

PY - 2021/2/26

Y1 - 2021/2/26

N2 - With this research we set out to develop a coumarin-based novel fluorescent probe NTR-AHC for the detection of biological thiols and nitroreductase (NTR). Probe NTR-AHC was constructed by attaching the NTR trigger moiety (p-nitrobenzyl) and biothiol acceptor (maleic acid monoamide), to the core fluorophore AHC. In the presence of both glutathione (GSH) and NTR, probe NTR-AHC produced a >8-fold increase in fluorescence intensity at 463 nm.

AB - With this research we set out to develop a coumarin-based novel fluorescent probe NTR-AHC for the detection of biological thiols and nitroreductase (NTR). Probe NTR-AHC was constructed by attaching the NTR trigger moiety (p-nitrobenzyl) and biothiol acceptor (maleic acid monoamide), to the core fluorophore AHC. In the presence of both glutathione (GSH) and NTR, probe NTR-AHC produced a >8-fold increase in fluorescence intensity at 463 nm.

U2 - 10.1016/j.tet.2020.131890

DO - 10.1016/j.tet.2020.131890

M3 - Article

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VL - 82

JO - Tetrahedron

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M1 - 131890

ER -

Coumarin-based fluorescent probe for the detection of glutathione and nitroreductase

Abstract

Funding

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