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/anie.200803897

Cited by 64 publications

(33 citation statements)

References 43 publications

(19 reference statements)

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“…10). These approaches have been used to produce several agents, including fialuridine, iodeoxyuridine (71), and metaiodobenzylguanidine (72), and have recently been applied to the production of 18 F-labeled compounds (73).…”

Section: Challenges In Probe Developmentmentioning

confidence: 99%

A Bridge Not Too Far: Linking Disciplines Through Molecular Imaging Probes

Valliant

2016

J. Nucl. Med. Technol.

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CE credit: For CE credit, you can access the test for this article, as well as additional JNMT CE tests, online at https://www.snmmilearningcenter.org. Complete the test online no later than September 2016. Your online test will be scored immediately. You may make 3 attempts to pass the test and must answer 80% of the questions correctly to receive 1.0 CEH (Continuing Education Hour) credit. SNMMI members will have their CEH credit added to their VOICE transcript automatically; nonmembers will be able to print out a CE certificate upon successfully completing the test. The online test is free to SNMMI members; nonmembers must pay $15.00 by credit card when logging onto the website to take the test.The field of nuclear medicine will rely increasingly on the discovery, proper evaluation, and clinical use of molecular imaging probes and on collaborations. Collaborations will include new initiatives among experts already involved in the field and with researchers, technologists, and clinicians from different areas of science and medicine. This article serves to highlight some of the opportunities in which molecular imaging and nuclear medicine in conjunction with probe development, new imaging technologies, and multidisciplinary collaborations can have a significant impact on health care and basic science from the perspective of a person involved in probe development. The article emphasizes breast cancer, but the concepts are readily applied to other areas of medicine and medical research. Nucl ear medicine is a unique field in that it relies on habitual collaboration between groups possessing disparate expertise. Nuclear medicine physicians work collaboratively on a daily basis with imaging physicists and nuclear medicine technologists who directly and indirectly rely on partnerships with biologists, chemists, engineers, and medical research teams to develop, validate, and produce radiopharmaceuticals. The future of nuclear medicine involves exploiting the full potential of molecular imaging and targeted radiotherapy and will require building on the existing culture of collaboration. To be truly successful, nuclear medicine will need to form bridges to groups outside the present sphere of collaboration-the underlying theme of this article.Society is facing challenging times that will shape the future of probe development. There has been a significant downturn in the world's economy that is affecting economic decisions made by consumers and governments, particularly with respect to health care. The world is in the midst of a protracted and ongoing isotope shortage, both an acute shortage associated with the shutdown of the reactor at Chalk River, limiting the supply of 99 Mo and 99m Tc, and a chronic underfunding of cyclotron laboratories. Economic pressures are affecting the way decisions are made about which new diagnostic technologies will ultimately be funded. This effect is true in public, private, and hybrid-model health-care systems, in which groups developing new probes must be conscious about both the healt...

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Section: Challenges In Probe Developmentmentioning

confidence: 99%

A Bridge Not Too Far: Linking Disciplines Through Molecular Imaging Probes

Valliant

2016

J. Nucl. Med. Technol.

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“…Compounds 7 and 9 (Scheme 6) were prepared using the published procedure. 6 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-Heptadecafluoro-10-iododecane was converted to (diaminomethylene) (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)sulfonium iodide (23) by reaction with thiourea in ethanol. This was further transformed into the sulfonyl chloride 24 and combined with phenylmethanol or 4-phenylbutan-1-ol to give the respective compound 7 or 9.…”

Section: Precursor Synthesismentioning

confidence: 99%

“…Compound 9, 6 Scheme 2, was labelled in 50% yield, compared with the previously published 88% radiochemical yield. 6 This indicates that the reactivity of the perfluoroalkyl chains and their possible interactions with [ 18 F]fluoride are clearly impacted by the hydrocarbon spacer.…”

Section: Introductionmentioning

confidence: 98%

“…As time is an important parameter in labelling chemistry, it would be advantageous to improve the reactivity of the leaving group and/or the ease of purification of a nucleophilic substitution reaction. 5 Fluorous-labelling strategies have previously been used in radiolabelling with 18 F, using perfluoro chains with two-carbon spacers, 6 as well as with other nuclides. A perfluoro leaving group has been used in the synthesis of [ 18 F]FDG, 7 and an iododemetalation 125 I-labelling reaction was achieved using a fluorine-rich tin support.…”

Section: Introductionmentioning

confidence: 99%

“…18 As a comparison, published labelling experiments that used a chain containing a two-carbon spacer between the fluorous chain and the sulfonyl group were repeated. 6 Compound 7, was labelled in 10% analytical radiochemical yield in acetonitrile at 1101C after 15 min. Compound 9, 6 Scheme 2, was labelled in 50% yield, compared with the previously published 88% radiochemical yield.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Use of perfluoro groups in nucleophilic ¹⁸F‐fluorination

Blom¹,

Karimi²,

Långström³

2009

Labelled Comp Radiopharmac

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Substrates with leaving groups that contained perfluoro moieties were investigated in labelling chemistry in order to exploit their properties to improve reactivity and purification. [18 F](Fluoromethyl)benzene was used as the model target compound. Precursors containing perfluoroalkyl and perfluoroaryl sulfonate moieties were subjected to nucleophilic 18 F-fluorination, and the impact of perfluoro groups on the substitution reaction and product purification was investigated. [ 18 F]Fluoride interacted with perfluoroalkyl chains, precluding nucleophilic substitution. When perfluoroaryl groups were used, the substitution proceeded, and the separation of product was explored. The radiolabelled product was obtained in 32% analytical yield and the radiochemical purity was increased to approximately 77% using fluorous solid phase extraction purification.

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