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Molecules. 2019 Aug 7;24(16). pii: E2866. doi: 10.3390/molecules24162866.

A Comprehensive Review of Non-Covalent Radiofluorination Approaches Using Aluminum [18F]fluoride: Will [18F]AlF Replace 68Ga for Metal Chelate Labeling?

Author information

1
Institut de Recherche en Cancérologie de Montpellier (IRCM), University of Montpellier, INSERM U1194, Montpellier Cancer Institute (ICM), 34298 Montpellier, France. cyril.fersing@icm.unicancer.fr.
2
Nuclear Medicine Department, Montpellier Cancer Institute (ICM), University of Montpellier, 208 Avenue des Apothicaires, 34298 Montpellier CEDEX 5, France. cyril.fersing@icm.unicancer.fr.
3
CERIMED, Aix-Marseille University, 13005 Marseille, France.
4
Centre de recherche en CardioVasculaire et Nutrition (C2VN), Aix-Marseille University, INSERM 1263, INRA 1260, 13385 Marseille, France.
5
Institut de Recherche en Cancérologie de Montpellier (IRCM), University of Montpellier, INSERM U1194, Montpellier Cancer Institute (ICM), 34298 Montpellier, France.
6
Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Université de Montpellier, ENSCM, UFR des Sciences Pharmaceutiques et Biologiques, 34093 Montpellier CEDEX, France.
7
Department of Nuclear Medicine, Aix-Marseille University, Assistance Publique-Hôpitaux de Marseille (AP-HM), 13385 Marseille, France.

Abstract

Due to its ideal physical properties, fluorine-18 turns out to be a key radionuclide for positron emission tomography (PET) imaging, for both preclinical and clinical applications. However, usual biomolecules radiofluorination procedures require the formation of covalent bonds with fluorinated prosthetic groups. This drawback makes radiofluorination impractical for routine radiolabeling, gallium-68 appearing to be much more convenient for the labeling of chelator-bearing PET probes. In response to this limitation, a recent expansion of the 18F chemical toolbox gave aluminum [18F]fluoride chemistry a real prominence since the late 2000s. This approach is based on the formation of an [18F][AlF]2+ cation, complexed with a 9-membered cyclic chelator such as NOTA, NODA or their analogs. Allowing a one-step radiofluorination in an aqueous medium, this technique combines fluorine-18 and non-covalent radiolabeling with the advantage of being very easy to implement. Since its first reports, [18F]AlF radiolabeling approach has been applied to a wide variety of potential PET imaging vectors, whether of peptidic, proteic, or small molecule structure. Most of these [18F]AlF-labeled tracers showed promising preclinical results and have reached the clinical evaluation stage for some of them. The aim of this report is to provide a comprehensive overview of [18F]AlF labeling applications through a description of the various [18F]AlF-labeled conjugates, from their radiosynthesis to their evaluation as PET imaging agents.

KEYWORDS:

NOTA; PET; aluminum fluoride; bifunctional chelating agent; coordination chemistry; molecular imaging; radiofluorination

PMID:
31394799
DOI:
10.3390/molecules24162866
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