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A solid-phase route to (18)F-labeled tracers, exemplified by the synthesis of [(18)F]2-fluoro-2-deoxy-D-glucose

A solid-phase route to (18)F-labeled tracers, exemplified by the synthesis of [(18)F]2-fluoro-2-deoxy-D-glucose
A solid-phase route to (18)F-labeled tracers, exemplified by the synthesis of [(18)F]2-fluoro-2-deoxy-D-glucose
Due to the short half-life of [18F] (half-life = 110min), the synthesis and purification ofradiotracers incorporating this positron-emitting radionuclide needs to be carried out as rapidly aspossible for applications in imaging using positron emission tomography (PET). Here we describe a conceptually new strategy for the synthesis of [18F]-containing molecules, which releases theradiotracer from a solid-supported precursor using limiting [18F]-fluoride. A major advantage overexisting solution methods lies in the fact that incorporation of the radionuclide occurs by means of nucleophilic displacement of a sulfonate ester linkage to the solid-phase, which occurs withconcomitant release of the radiotracer into solution. The vast excess of precursor that istraditionally employed remains attached to the solid-phase and is removed by simple filtration. The potential of the methodology is illustrated by the synthesis of the most important and widelyused [18F]-radiotracer 2-[18F]-fluoro-2-deoxyglucose (FDG) with good radiochemical yield (73%,decay corrected) and superior chemical purity.
medical imaging, positron emission tomography, solid-phase synthesis, triflate linker, fluorination
1433-7851
941-944
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Bouvet, Denis R.
f0b8b86f-3470-42ed-95a7-4e7ac6870a22
Champion, Sue
9f8f6e1a-d1e8-4bca-93bb-029982552fb7
Gibson, Alex M.
8a1e0997-db08-45c9-9597-aca8dee8c79e
Hu, Yulai
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Jackson, Alex
352997fe-a55f-4c72-8b2d-a1e951889de7
Khan, Imtiaz
472f2db0-2192-4200-b2a7-9ac4cc798fd9
Ma, Nianchun
f911e90a-c94d-494d-812c-5a55ba99e66f
Millot, Nicholas
66cec4c6-a989-458e-8340-c93ee35dd37f
Wadsworth, Harry
f337a299-e45d-45d6-936e-75c88492270f
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Bouvet, Denis R.
f0b8b86f-3470-42ed-95a7-4e7ac6870a22
Champion, Sue
9f8f6e1a-d1e8-4bca-93bb-029982552fb7
Gibson, Alex M.
8a1e0997-db08-45c9-9597-aca8dee8c79e
Hu, Yulai
5f6957ca-475f-42b3-892f-e2d64cf2ef11
Jackson, Alex
352997fe-a55f-4c72-8b2d-a1e951889de7
Khan, Imtiaz
472f2db0-2192-4200-b2a7-9ac4cc798fd9
Ma, Nianchun
f911e90a-c94d-494d-812c-5a55ba99e66f
Millot, Nicholas
66cec4c6-a989-458e-8340-c93ee35dd37f
Wadsworth, Harry
f337a299-e45d-45d6-936e-75c88492270f
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Brown, Lynda J., Bouvet, Denis R., Champion, Sue, Gibson, Alex M., Hu, Yulai, Jackson, Alex, Khan, Imtiaz, Ma, Nianchun, Millot, Nicholas, Wadsworth, Harry and Brown, Richard C.D. (2007) A solid-phase route to (18)F-labeled tracers, exemplified by the synthesis of [(18)F]2-fluoro-2-deoxy-D-glucose. Angewandte Chemie International Edition, 46 (6), 941-944. (doi:10.1002/anie.200603394). (PMID:17183499)

Record type: Article

Abstract

Due to the short half-life of [18F] (half-life = 110min), the synthesis and purification ofradiotracers incorporating this positron-emitting radionuclide needs to be carried out as rapidly aspossible for applications in imaging using positron emission tomography (PET). Here we describe a conceptually new strategy for the synthesis of [18F]-containing molecules, which releases theradiotracer from a solid-supported precursor using limiting [18F]-fluoride. A major advantage overexisting solution methods lies in the fact that incorporation of the radionuclide occurs by means of nucleophilic displacement of a sulfonate ester linkage to the solid-phase, which occurs withconcomitant release of the radiotracer into solution. The vast excess of precursor that istraditionally employed remains attached to the solid-phase and is removed by simple filtration. The potential of the methodology is illustrated by the synthesis of the most important and widelyused [18F]-radiotracer 2-[18F]-fluoro-2-deoxyglucose (FDG) with good radiochemical yield (73%,decay corrected) and superior chemical purity.

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e-pub ahead of print date: 20 December 2006
Published date: 29 January 2007
Keywords: medical imaging, positron emission tomography, solid-phase synthesis, triflate linker, fluorination

Identifiers

Local EPrints ID: 44202
URI: http://eprints.soton.ac.uk/id/eprint/44202
ISSN: 1433-7851
PURE UUID: b3a7ba01-e5bf-472f-8f16-2e0e08ec80f1
ORCID for Lynda J. Brown: ORCID iD orcid.org/0000-0002-5678-0814
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 19 Feb 2007
Last modified: 16 Mar 2024 03:00

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Contributors

Author: Lynda J. Brown ORCID iD
Author: Denis R. Bouvet
Author: Sue Champion
Author: Alex M. Gibson
Author: Yulai Hu
Author: Alex Jackson
Author: Imtiaz Khan
Author: Nianchun Ma
Author: Nicholas Millot
Author: Harry Wadsworth

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