Comparison between [ 18 F]fluorination and [ 18 F]fluoroethylation reactions for the synthesis of the PDE10A PET radiotracer [ 18 F]MNI-659

Mori, Wakana; Takei, Makoto; Furutsuka, Kenji; Fujinaga, Masayuki; Kumata, Katsushi; Muto, Masatoshi; Ohkubo, Takayuki; Hashimoto, H.; Tamagnan, Gilles; Higuchi, Makoto; Kawamura, Kazunori; Zhang, Ming‐Rong

doi:10.1016/j.nucmedbio.2017.08.002

Cited by 7 publications

(14 citation statements)

References 39 publications

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“…Radiosynthesis of [ 11 C]PBB3, a specific PET tracer for aggregated filamentous tau protein, was described previously 29 . [ 18 F]MNI659, a highly selective antagonist against phosphodiesterase 10A (PDE10A), was radiosynthesized by previously described methods 37 . [ 11 C]GF120918 and [ 11 C]verapamil were radiosynthesized as described previously 36 .…”

Section: Methodsmentioning

confidence: 99%

Genetically targeted reporter imaging of deep neuronal network in the mammalian brain

Shimojo

Ono

Takuwa

et al. 2020

Preprint

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Positron Emission Tomography (PET) allows biomolecular tracking, while PET monitoring of brain networks has been hampered by the lack of a suitable reporter. Here, we describe invivo brain reporters utilizing bacterial dihydrofolate reductase, ecDHFR, and its antagonist, TMP. In mice, peripheral administration of radiofluorinated and fluorescent TMP analogs enabled PET and intravital microscopy, respectively, of neuronal ecDHFR expressions. This technique was applicable to the visualization of chemogenetically provoked neuronal ensemble activities in the hippocampus. Notably, ecDHFR-PET captured neuronal projections in non-human primate brains, indicating the availability of ecDHFR-based techniques for network monitoring. Finally, we demonstrated PET assays of turnover and self-assembly of proteins tagged with ecDHFR mutants. Collectively, the current reporter technology offers diverse in-vivo molecular analyses of a brain circuit.

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Section: Methodsmentioning

confidence: 99%

Genetically targeted reporter imaging of deep neuronal network in the mammalian brain

Shimojo

Ono

Takuwa

et al. 2020

Preprint

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“…Regarding the radiosynthesis of [ 18 F]30, Mori et al [138] reported on the comparison between direct 18 F-labeling of the corresponding tosylate precursor as previously described by Barret et al [122] and a two-step approach by 18 F-labeling of bromoethyl triflate and using the resulting 1-bromo-2-[ 18 F]fluoroethane for 18 F-fluoroethylation of the respective phenol precursor (see Scheme 12). The aim was to establish an appropriate strategy for routine production of the radioligand with high quality and sufficient activity for clinical application using an in-house developed automated multi-purpose synthesizer [138,139]. Regarding the radiosynthesis of [ 18 F]30, Mori et al [138] reported on the comparison between direct 18 F-labeling of the corresponding tosylate precursor as previously described by Barret et al [122] and a two-step approach by 18 F-labeling of bromoethyl triflate and using the resulting 1-bromo-2-[ 18 F]fluoroethane for 18 F-fluoroethylation of the respective phenol precursor (see Scheme 12).…”

Section: Recent Pet Studies Using Already Known Pde10a Radioligandsmentioning

confidence: 99%

“…The aim was to establish an appropriate strategy for routine production of the radioligand with high quality and sufficient activity for clinical application using an in-house developed automated multi-purpose synthesizer [138,139]. Regarding the radiosynthesis of [ 18 F]30, Mori et al [138] reported on the comparison between direct 18 F-labeling of the corresponding tosylate precursor as previously described by Barret et al [122] and a two-step approach by 18 F-labeling of bromoethyl triflate and using the resulting 1-bromo-2-[ 18 F]fluoroethane for 18 F-fluoroethylation of the respective phenol precursor (see Scheme 12). The aim was to establish an appropriate strategy for routine production of the radioligand with high quality and sufficient activity for clinical application using an in-house developed automated multi-purpose synthesizer [138,139].…”

Section: Recent Pet Studies Using Already Known Pde10a Radioligandsmentioning

confidence: 99%

“…For these purposes, the D2/3R-dual specific radioligand [ 11 C]raclopride and the PDE10A-selective radioligand [ 18 F]30 have been applied for brain PET imaging in a cohort Scheme 12. Radiosynthesis of [ 18 F]30 by (A) direct 18 F-labeling of the tosylate precursor and (B) two-step approach via 18 F-fluoroethylation of the phenol precursor [138]. Mori et al found out that the radiolabeling efficiency of the direct nucleophilic aliphatic substitution of the tosylate group using the K + /[ 18 F]F − /K 2.2.2 -carbonate complex is highly dependent on the amounts of precursor and potassium carbonate [138].…”

Section: Recent Pet Studies Using Already Known Pde10a Radioligandsmentioning

confidence: 99%

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Challenges on Cyclic Nucleotide Phosphodiesterases Imaging with Positron Emission Tomography: Novel Radioligands and (Pre-)Clinical Insights since 2016

Schröder

Scheunemann

Wenzel

et al. 2021

IJMS

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Cyclic nucleotide phosphodiesterases (PDEs) represent one of the key targets in the research field of intracellular signaling related to the second messenger molecules cyclic adenosine monophosphate (cAMP) and/or cyclic guanosine monophosphate (cGMP). Hence, non-invasive imaging of this enzyme class by positron emission tomography (PET) using appropriate isoform-selective PDE radioligands is gaining importance. This methodology enables the in vivo diagnosis and staging of numerous diseases associated with altered PDE density or activity in the periphery and the central nervous system as well as the translational evaluation of novel PDE inhibitors as therapeutics. In this follow-up review, we summarize the efforts in the development of novel PDE radioligands and highlight (pre-)clinical insights from PET studies using already known PDE radioligands since 2016.

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“…This direct [ 18 F] uorination was achieved within the same reaction vessel in an automated synthesizer. Moreover, the one-step radiolabeling technique for 18 F-labeled tracers could be readily transferred to other PET centers to perform multisite studies using the same study protocol (Kawamura et al 2016;Kawamura et al 2021;Mori et al 2017). In fact, automated radiosynthesis of [ 18 F]PM-PBB3 by direct [ 18 F] uorination has been transferred to a dozen of PET centers in Japan, China, Taiwan, and the USA (Hsu et al 2020;Su et al 2020;Weng et al 2020).…”

Section: Introductionmentioning

confidence: 99%

Automated radiosynthesis of two 18F-labeled tracers containing 3-fluoro-2-hydroxypropyl moiety, [18F]FMISO and [18F]PM-PBB3, via [18F]epifluorohydrin

Kawamura

Ohkubo

Kurihara

et al. 2021

Preprint

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Background [18F]Fluoromisonidazole ([18F]FMISO) and 1-[18F]fluoro-3-((2-((1E,3E)-4-(6-(methylamino)pyridine-3-yl)buta-1,3-dien-1-yl)benzo[d]thiazol-6-yl)oxy)propan-2-ol ([18F]PM-PBB3 or [18F]APN-1607) are clinically used radiotracers for imaging for hypoxia and tau pathology, respectively. Both radiotracers were produced by direct [18F]fluorination using the corresponding tosylate precursors 1 or 2 and [18F]F−, followed by the removal of protecting groups. In this study, we synthesized [18F]FMISO and [18F]PM-PBB3 by [18F]fluoroalkylation using [18F]epifluorohydrin ([18F]5) for clinical applications. Results First, [18F]5 was synthesized by the reaction of 1,2-epoxypropyl tosylate (8) with [18F]F− and was purified by distillation. Subsequently, [18F]5 was reacted with 2-nitroimidazole (6) or PBB3 (7) as a precursor for 18F-labeling, and each reaction mixture was refined by semipreparative high-performance liquid chromatography and formulation to obtain the [18F]FMISO or [18F]PM-PBB3 injection. All synthetic sequences were performed using an automated 18F-labeling synthesizer. The [18F]FMISO thus obtained showed sufficient radioactivity (0.83 ± 0.20 GBq at the end of synthesis; n = 8) with appropriate radiochemical yield based on [18F]F− (26 ± 7.5% at the end of irradiation with decay-corrected; n = 8). [18F]PM-PBB3 thus obtained showed sufficient radioactivity (0.79 ± 0.10 GBq; n = 11) with appropriate radiochemical yield based on [18F]F− (16 ± 3.2% at the end of irradiation with decay-corrected; n = 11). Conclusions Both [18F]FMISO and [18F]PM-PBB3 injections were successfully synthesized with sufficient radioactivity by [18F]fluoroalkylation using [18F]5.

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Comparison between [ 18 F]fluorination and [ 18 F]fluoroethylation reactions for the synthesis of the PDE10A PET radiotracer [ 18 F]MNI-659

Cited by 7 publications

References 39 publications

Genetically targeted reporter imaging of deep neuronal network in the mammalian brain

Genetically targeted reporter imaging of deep neuronal network in the mammalian brain

Challenges on Cyclic Nucleotide Phosphodiesterases Imaging with Positron Emission Tomography: Novel Radioligands and (Pre-)Clinical Insights since 2016

Automated radiosynthesis of two 18F-labeled tracers containing 3-fluoro-2-hydroxypropyl moiety, [18F]FMISO and [18F]PM-PBB3, via [18F]epifluorohydrin

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