Preparation of N.C.A. [17‐<sup>18</sup>F]‐fluoroheptadecanoic acid in high yields via aminopolyether supported, nucleophilic fluorination

Coenen, Heinrich Hubert; Schüller, Manfred; Stöcklin, G.; Klatte, Bernd; Knöchel, A.

doi:10.1002/jlcr.2580230502

Cited by 107 publications

(43 citation statements)

References 6 publications

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“…47,48 All three precursors for labelling synthesized above (derivatives 8, 9 and 11) were tested within a range of 10-30 mmol engaged per run. DMSO as the solvent and 1651C as the temperature were selected for these reactions based on literature, 49,50 whereas different times of reaction were studied.…”

Section: Chemistrymentioning

confidence: 99%

[¹⁸F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

Kühnast

Hinnen

Tavitian

et al. 2008

Labelled Comp Radiopharmac

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FPyKYNE (2‐fluoro‐3‐pent‐4‐yn‐1‐yloxypyridine) is a novel fluoropyridine‐based structure, designed for the fluorine‐18 labelling of macromolecules using copper‐catalysed Huisgen 1,3‐dipolar cycloaddition (click chemistry). FPyKYNE (non‐labelled as reference), as well as the 2‐bromo, 2‐nitro and 2‐trimethylammonium analogues (as precursors for labelling with fluorine‐18), was synthesized in 44, 95, 60 and 41%, respectively, from commercially available 5‐chloropent‐1‐yne and the appropriate 2‐substituted‐3‐hydroxypyridines. [18F]FPyKYNE was synthesized in one single radiochemical step by reaction of no‐carrier‐added K[18F]F‐Kryptofix®222 (DMSO, 165°C, 3–5 min) followed by C‐18 SepPak cartridge pre‐purification and finally semi‐preparative HPLC purification on a Hewlett Packard SiO2 Zorbax® Rx‐SIL. Using the 2‐nitropyridine or the pyridin‐2‐yltrimethylammonium trifluoromethanesulphonate precursor for labelling (30 and 10 µmol, respectively), incorporation yields up to 90% were observed and 7.0–8.9 GBq (190–240 mCi) of [18F]FPyKYNE ([18F]‐1) could be isolated within 60–70 min (HPLC purification included), starting from a 37.0 GBq (1.0 Ci) [18F]fluoride batch (overall decay‐corrected and isolated yields: 30–35%). Copyright © 2008 John Wiley & Sons, Ltd.

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Section: Chemistrymentioning

confidence: 99%

[¹⁸F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

Kühnast

Hinnen

Tavitian

et al. 2008

Labelled Comp Radiopharmac

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“…This approach allowed no carrier added (n.c.a) introduction of F-18 by nucleophilic substitution. 5 As leaving group the p-tosyloxy residue was chosen. Before starting the F-18 labelling we had to synthesize the reference compound 5 and the precursor 10.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of [¹⁸F]Fluoroclofilium as a potential cardiac imaging agent for PET studies

Yu¹,

Kim²,

Kim³

et al. 2003

Labelled Comp Radiopharmac

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Summary N-4-(4-chlorophenyl)butyl-N,N-diethyl-7-[18 F]fluoroheptylammonium ([ 18 F]-fluoroclofilium) has been prepared as a potential cardiac imaging agent. For the synthesis of this radiolabelled ammonium salt, its tosyloxylated analogue was prepared as a precursor, and the non-radioactive fluorine analogue was synthesized as a reference compound. Radiofluorination was achieved by the treatment of N-4-(4-chlorophenyl)butyl-N,N-diethyl-7-(p-toluenesulfonyloxy)-heptylammonium p-toluenesulfonate with 18 F À in the presence of Kryptofix-2.2.2 in acetonitrile.

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“…The major impetus came through the production of 18 F in large quantities via the 18 O( p, n) 18 F reaction [13,16] at a small cyclotron followed by a simplified method of nucleophilic substitution by 18 F in organic molecules [17]. This led in particular to the preparation of the most frequently used PET-tracer 2-[…”

Section: Positron Emitters For Petmentioning

confidence: 99%

The present and future of medical radionuclide production

Qaim

2012

Radiochimica Acta

103

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Reactor and cyclotron production of medical radionuclides / γ -ray emitters for SPECT / Positron emitters for PET / Corpuscular radiation emitters for internal radiotherapy / Low and intermediate energy nuclear reactions / Radionuclide generators / Future directionsSummary. Medical radionuclide production technology is well established. Both reactors and cyclotrons are utilized for production; the positron emitters, however, are produced exclusively using cyclotrons. A brief survey of the production methods of most commonly used diagnostic and therapeutic radionuclides is given. The emerging radionuclides are considered in more detail. They comprise novel positron emitters and therapeutic radionuclides emitting low-range electrons and α-particles. The possible alternative production routes of a few established radionuclides, like 68 Ga and 99m Tc, are discussed. The status of standardisation of production data of the commonly used as well as of some emerging radionuclides is briefly mentioned. Some notions on anticipated future trends in the production and application of radionuclides are considered.

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Preparation of N.C.A. [17‐¹⁸F]‐fluoroheptadecanoic acid in high yields via aminopolyether supported, nucleophilic fluorination

Cited by 107 publications

References 6 publications

[¹⁸F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

[¹⁸F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

Synthesis of [¹⁸F]Fluoroclofilium as a potential cardiac imaging agent for PET studies

The present and future of medical radionuclide production

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Preparation of N.C.A. [17‐18F]‐fluoroheptadecanoic acid in high yields via aminopolyether supported, nucleophilic fluorination

Cited by 107 publications

References 6 publications

[18F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

[18F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

Synthesis of [18F]Fluoroclofilium as a potential cardiac imaging agent for PET studies

The present and future of medical radionuclide production

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Product

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Preparation of N.C.A. [17‐¹⁸F]‐fluoroheptadecanoic acid in high yields via aminopolyether supported, nucleophilic fluorination

[¹⁸F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

[¹⁸F]FPyKYNE, a fluoropyridine‐based alkyne reagent designed for the fluorine‐18 labelling of macromolecules using click chemistry

Synthesis of [¹⁸F]Fluoroclofilium as a potential cardiac imaging agent for PET studies