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

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

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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SDG 3 Good Health and Well-being

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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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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. ",

year = "2015",

month = sep,

day = "11",

doi = "10.1039/C5CC05013H",

language = "English",

volume = "51",

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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

Y1 - 2015/9/11

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.

AB - 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.

UR - http://www.rsc.org/suppdata/c5/cc/c5cc05013h/c5cc05013h1.pdf

U2 - 10.1039/C5CC05013H

DO - 10.1039/C5CC05013H

M3 - Article

SN - 1359-7345

VL - 51

SP - 13542

EP - 13545

JO - Chemical Communications

JF - Chemical Communications

IS - 70

ER -

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