A two-step fluorinase enzyme mediated 18F labelling of an RGD peptide for positron emission tomography

Stephen Thompson; Mayca Ónega; Sharon Ashworth; Ian N. Fleming; Jan Passchier; David O'Hagan

doi:10.1039/C5CC05013H

A two-step fluorinase enzyme mediated ¹⁸F labelling of an RGD peptide for positron emission tomography

Stephen Thompson, Mayca Ónega, Sharon Ashworth, Ian N. Fleming , Jan Passchier , David O'Hagan

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Abstract

A two-step radiolabelling protocol of a cancer relevant cRGD peptide is described where the fluorinase enzyme is used to catalyse a transhalogenation reaction to generate [¹⁸F]-5'-fluoro-5'-deoxy-2-ethynyladenosine, [¹⁸F]FDEA, followed by a ‘click’ reaction to an azide tethered cRGD peptide. This protocol offers an efficient radiolabelling of a biologically relevant peptide construct in water at pH 7.8, 37^oC in 2 hours, that was metabolically stable in rats and retained high affinity for the α_Vβ₃ integrin.

Original language	English
Pages (from-to)	13542-13545
Journal	Chemical Communications
Volume	51
Issue number	70
Early online date	17 Jul 2015
DOIs	https://doi.org/10.1039/C5CC05013H
Publication status	Published - 11 Sept 2015

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10.1039/C5CC05013H

OHagan_2015_ChemComm_TwoStep_CC
Copyright 2015 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
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Cite this

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title = "A two-step fluorinase enzyme mediated 18F labelling of an RGD peptide for positron emission tomography",

abstract = "A two-step radiolabelling protocol of a cancer relevant cRGD peptide is described where the fluorinase enzyme is used to catalyse a transhalogenation reaction to generate [18F]-5'-fluoro-5'-deoxy-2-ethynyladenosine, [18F]FDEA, followed by a {\textquoteleft}click{\textquoteright} reaction to an azide tethered cRGD peptide. This protocol offers an efficient radiolabelling of a biologically relevant peptide construct in water at pH 7.8, 37oC in 2 hours, that was metabolically stable in rats and retained high affinity for the αVβ3 integrin.",

author = "Stephen Thompson and Mayca {\'O}nega and Sharon Ashworth and Fleming, {Ian N.} and Jan Passchier and David O'Hagan",

note = "The authors thank EPSRC and the Scottish Imaging Network (SINAPSE) for grants. DO{\textquoteright}H thanks the Royal Society for a Wolfson Research Merit Award and ST is grateful to the John and Kathleen Watson Scholarship for financial support. ",

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doi = "10.1039/C5CC05013H",

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T1 - A two-step fluorinase enzyme mediated 18F labelling of an RGD peptide for positron emission tomography

AU - Thompson, Stephen

AU - Ónega, Mayca

AU - Ashworth, Sharon

AU - Fleming , Ian N.

AU - Passchier , Jan

AU - O'Hagan, David

N1 - The authors thank EPSRC and the Scottish Imaging Network (SINAPSE) for grants. DO’H thanks the Royal Society for a Wolfson Research Merit Award and ST is grateful to the John and Kathleen Watson Scholarship for financial support.

PY - 2015/9/11

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N2 - A two-step radiolabelling protocol of a cancer relevant cRGD peptide is described where the fluorinase enzyme is used to catalyse a transhalogenation reaction to generate [18F]-5'-fluoro-5'-deoxy-2-ethynyladenosine, [18F]FDEA, followed by a ‘click’ reaction to an azide tethered cRGD peptide. This protocol offers an efficient radiolabelling of a biologically relevant peptide construct in water at pH 7.8, 37oC in 2 hours, that was metabolically stable in rats and retained high affinity for the αVβ3 integrin.

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DO - 10.1039/C5CC05013H

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A two-step fluorinase enzyme mediated ¹⁸F labelling of an RGD peptide for positron emission tomography

Abstract

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Extending fluorinase C-18F-bond: Extending fluorinase [C-18F]-bond biocatalysis for Positron Emission Tomography (PET)

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A two-step fluorinase enzyme mediated 18F labelling of an RGD peptide for positron emission tomography

Abstract

UN SDGs

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Extending fluorinase C-18F-bond: Extending fluorinase [C-18F]-bond biocatalysis for Positron Emission Tomography (PET)

Cite this

A two-step fluorinase enzyme mediated ¹⁸F labelling of an RGD peptide for positron emission tomography