Precision Radiochemistry for Fluorine‐18 Labeling of
            <scp>PET</scp>
            Tracers

Rong, Jian; Haider, Ahmed; Liang, Steven H.

doi:10.1002/9783527825158.ch12

Cited by 3 publications

(1 citation statement)

References 90 publications

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“…The aprotic conditions in SN2 nucleophilic reactions are very important for the reactivity of fluoride, as a nucleophile. This reaction mechanism is the most prominent reaction in the production of a variety of clinically relevant [ 18 F]Fradiopharmaceuticals, using common leaving groups such as sulfonic acid esters or halides [2, 17,18]. Fluoride ions in water as strongly hydrated anion is generally unreactive in nucleophilic substitution reactions.…”

Section: Resultsmentioning

confidence: 99%

Optimization of reaction conditions for synthesis of [18F]FMISO using stable [19F]F-

CHOCHEVSKA,

KOLEVSKA,

LAZAREVA

et al. 2023

jrp

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The increasing number of fluorinated pharmaceuticals in pharmaceutical chemistry and fluorine radiopharmaceuticals in radiochemistry highlights the importance of optimizing their synthesis processes.[ 18 F]Fluoromisonidazole ([ 18 F]FMISO) radiopharmaceutical synthesized using aqueous [ 18 F]Fand 1-(2'-nitro-1'imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulfonylpropanediol precursor (NITTP), is one such example. This radiolabeled compound is used for imaging tumor hypoxia by positron emission tomography (PET). When working with ionizing radiation, ensuring the operator's safety is crucial. As a result, the synthesis process for [ 18 F]FMISO takes place within automated modules in closed lead-shielded hot cells. This protective measure prohibits the collection of control samples during the synthesis process. Our experiments involved utilizing the stable isotope [ 19 F]Finstead of [ 18 F]Fto examine various aspects. These included analyzing the intermediate compound produced after the fluorination reaction, assessing unhydrolyzed/hydrolyzed intermediates, and detecting unexpected or unknown chemical impurities in both the unpurified and final purified products. HPLC analysis was employed to analyze the collected samples. The results obtained from these experiments proved invaluable in addressing the challenge of unwanted chemical impurities during the radiosynthesis of [ 18 F]FMISO. They provided valuable insights that aided in the further development of the synthesis process. Overall, this study demonstrates the significance of utilizing nonradioactive chemistry to optimize radiosynthesis, allowing for the safe and efficient production of [ 18 F]FMISO without the need for radiation exposure.

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Section: Resultsmentioning

confidence: 99%

Optimization of reaction conditions for synthesis of [18F]FMISO using stable [19F]F-

CHOCHEVSKA,

KOLEVSKA,

LAZAREVA

et al. 2023

jrp

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Difluoromethoxide Is a Strong Leaving Group in the Photoredox Deoxyradiofluorination of 2-Phenylpyridines

Jiang,

Ellin,

Telu

et al. 2024

J. Org. Chem.

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A 2-phenyl-3-difluoromethoxy-pyridinyl moiety features in potent phosphodiesterase 4D inhibitors that are considered to be candidate radiotracers for positron emission tomography if they are labeled with fluorine-18. Fluorine-18 could be installed as desired at the 3′-phenyl position with acridinium-mediated photoredox radiodeoxyfluorination in homologues bearing variously substituted 3′-aryloxy groups. However, a distal 3-difluoromethoxide (-OCHF 2 ) group strongly competes as a leaving group, especially when an electron-deficient aryloxy group is present at position 3′. A yield of up to 50% may occur without observable 19 F for 18 F exchange.

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Aryl Radical Enabled, Copper-Catalyzed Sonogashira-Type Cross-Coupling of Alkynes with Alkyl Iodides

et al. 2023

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Despite the success of Sonogashira coupling for the synthesis of arylalkynes and conjugated enynes, the engagement of unactivated alkyl halides in such reactions remains historically challenging. We report herein a strategy that merges Cu-catalyzed alkyne transfer with the aryl radical activation of carbon–halide bonds to enable a general approach for the coupling of alkyl iodides with terminal alkynes. This unprecedented Sonogashira-type cross-coupling reaction tolerates a broad range of functional groups and has been applied to the late-stage cross-coupling of densely functionalized pharmaceutical agents as well as the synthesis of positron emission tomography tracers.

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Precision Radiochemistry for Fluorine‐18 Labeling of PET Tracers

Cited by 3 publications

References 90 publications

Optimization of reaction conditions for synthesis of [18F]FMISO using stable [19F]F-

Optimization of reaction conditions for synthesis of [18F]FMISO using stable [19F]F-

Difluoromethoxide Is a Strong Leaving Group in the Photoredox Deoxyradiofluorination of 2-Phenylpyridines

Aryl Radical Enabled, Copper-Catalyzed Sonogashira-Type Cross-Coupling of Alkynes with Alkyl Iodides

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