Fluorous Synthesis of <sup>18</sup>F Radiotracers with the [<sup>18</sup>F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process

Béjot, Romain; Fowler, Thomas; Carroll, Laurence; Boldon, Sophie; Moore, Jane E.; Declerck, Jérôme; Gouverneur, Véronique

doi:10.1002/ange.200803897

Cited by 17 publications

(10 citation statements)

References 43 publications

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“…The goal of this paper was the development of a simplified purification procedure based on fluorous solid phase extraction (FSPE) using highly fluorinated starting materials. In a previous publication, 2‐[ 18 F]fluoroethyl azide ([ 18 F] 15 ) was successfully synthesized from the perfluorinated sulfonate precursor 52 . [ 18 F] 15 was obtained in an RCY of 76% and a molar activity of 10 GBq/μmol after purification via FSPE.…”

Section: Indirect Approachmentioning

confidence: 99%

Recent progress using the Staudinger ligation for radiolabeling applications

Mamat

Gott

Steinbach

2018

Labelled Comp Radiopharmac

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The increasing application of positron emission tomography and single-photon emission computer tomography in radiopharmacy and nuclear medicine has stimulated the development of a multitude of novel and versatile bioorthogonal conjugation techniques. Currently, there is particular interest in radiolabeling biologically active, high molecular weight compounds like peptides, proteins, or antibodies, but also for the labeling of small organic compounds. An enormous challenge in radiolabeling these biologically active molecules is that the introduction of radiohalogens like fluorine-18 as well as various radiometals proceeds under harsh conditions, which could destroy the biomolecule. The Staudinger ligation is one of the most powerful bioorthogonal conjugation techniques. The reaction proceeds over wide temperature and pH ranges; an amide (peptide) bond is formed as the ligation unit, which minimizes distortion of the structure; no isomers are obtained; and the reaction proceeds without any metal catalyst. Due to this adaptability, this robust ligation type is a perfect candidate with a high potential for various applications in the field of radiopharmacy for the labeling of biomolecules under mild conditions. This review summarizes recent research concerning the implementation of the Staudinger ligation for radiolabeling applications.

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Section: Indirect Approachmentioning

confidence: 99%

Recent progress using the Staudinger ligation for radiolabeling applications

Mamat

Gott

Steinbach

2018

Labelled Comp Radiopharmac

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“…Several patents also describe novel uses of SPE processes for the purification of [ 18 F]fluorinated products. For example, Isis Innovation Limited patented a strategy [28] that was also later reported in the academic literature [29] for improving the speed and ease of purification of [ 18 F]-labeled radiotracers and radioligands by making use of precursors bearing perfluorinated sulfonyl-leaving groups ( Figure 2C). The described isolation/purification strategy relies on 'fluorous detagging', whereby reaction of perfluorinated precursor with [ 18 F]fluoride results in the production of the desired (monofluorinated) radiolabeled product, along with a perfluorinated sulfonate anion.…”

Section: Purification Technologymentioning

confidence: 99%

Fluorine-18 Patents (2009–2015). Part 2: New Radiochemistry

et al. 2016

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Fluorine-18 ((18)F) is one of the most common positron-emitting radionuclides used in the synthesis of positron emission tomography radiotracers due to its ready availability, convenient half-life and outstanding imaging properties. In Part 1 of this review, we presented the first analysis of patents issued for novel radiotracers labeled with fluorine-18. In Part 2, we follow-up with a focus on patents issued for new radiochemistry methodology using fluorine-18 issued between January 2009 and December 2015.

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“…The purification step of this labeling reaction was improved using fluorous solid phase extraction (FSPE). For this purpose, derivative 132 was prepared with a fluorous tag [139] (C 4 F 9 chain on the aromatic ring of the phosphane) attached onto the phosphino fragment. Adversely, this compound was faster oxidized to the corresponding phosphine than the non fluorous counterpart.…”

Section: Staudinger Ligationmentioning

confidence: 99%