Development of carbon-11 labeled acryl amides for selective PET imaging of active tissue transglutaminase

Wildt, Berend van der; Wilhelmus, Micha M.M.; Bijkerk, Jonne; Haveman, Lizeth Y.F.; Kooijman, Esther; Schuit, Robert C.; Bol, John G.J.M.; Jongenelen, Cornelis A.M.; Lammertsma, Adriaan A.; Drukarch, Benjamin; Windhorst, Albert D.

doi:10.1016/j.nucmedbio.2016.01.003

Cited by 30 publications

(38 citation statements)

References 36 publications

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“…148 Several radiotracer development efforts have attempted to leverage the combinatorial potential of metal-catalyzed 11 C-carbonylation for targets including TSPO, EGFR, VEGFR-2, VAChT, and TG2. 155,165–168 It is hoped that recent advances in production and handling of [ 11 C]CO will unlock this highly versatile reagent for greater use in novel radiotracer development efforts in the near future.…”

Section: [11c]co Carbonylationmentioning

confidence: 99%

¹¹CO bonds made easily for positron emission tomography radiopharmaceuticals

et al. 2016

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The positron-emitting radionuclide carbon-11 (11C, t1/2 = 20.3 minutes) possesses the unique potential for radiolabeling of any biological, naturally occurring, or synthetic organic molecule for in vivo positron emission tomography (PET) imaging. Carbon-11 is most often incorporated into small molecules by methylation of alcohol, thiol, amine or carboxylic acid precursors using [11C]methyl iodide or [11C]methyl triflate (generated from [11C]CO2). Consequently, small molecules that lack an easily substituted 11C-methyl group are often considered to have non-obvious strategies for radiolabeling and require a more customized approach. [11C]Carbon dioxide, [11C]carbon monoxide, [11C]cyanide, and [11C]phosgene represent alternative carbon-11 reactants to enable 11C-carbonylation. Methodologies developed for preparation of 11C-carbonyl groups have had a tremendous impact on the development of novel PET radiopharmaceuticals and provided key tools for clinical research. 11C-Carbonyl radiopharmaceuticals based on labeled carboxylic acids, amides, carbamates, and ureas now account for a substantial number of important imaging agents that have seen translation to higher species and clinical research of previously inaccessible targets, which is a testament to the creativity, utility, and practicality of the underlying radiochemistry.

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Section: [11c]co Carbonylationmentioning

confidence: 99%

¹¹CO bonds made easily for positron emission tomography radiopharmaceuticals

et al. 2016

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“…4). Windhorst et al produced three 11 C-labeled acryl amide radioligands for in vivo PET imaging of the tissue transglutaminase (TG2) enzyme [63]. Moreover, with the “xenon-method” as the synthesis platform, the Uppsala-group presented two novel approaches to 11 C-carbonyl labeled compounds.…”

Section: Carbonylation Reactions Using 11comentioning

confidence: 99%

New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals

Dahl

Halldin

Schou

2017

Clin Transl Imaging

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PurposeThis short review aims to cover the more recent and promising developments of carbon-11 (11C) labeling radiochemistry and its utility in the production of novel radiopharmaceuticals, with special emphasis on methods that have the greatest potential to be translated for clinical positron emission tomography (PET) imaging.MethodsA survey of the literature was undertaken to identify articles focusing on methodological development in 11C chemistry and their use within novel radiopharmaceutical preparation. However, since 11C-labeling chemistry is such a narrow field of research, no systematic literature search was therefore feasible. The survey was further restricted to a specific timeframe (2000–2016) and articles in English.ResultsFrom the literature, it is clear that the majority of 11C-labeled radiopharmaceuticals prepared for clinical PET studies have been radiolabeled using the standard heteroatom methylation reaction. However, a number of methodologies have been developed in recent years, both from a technical and chemical point of view. Amongst these, two protocols may have the greatest potential to be widely adapted for the preparation of 11C-radiopharmaceuticals in a clinical setting. First, a novel method for the direct formation of 11C-labeled carbonyl groups, where organic bases are utilized as [11C]carbon dioxide-fixation agents. The second method of clinical importance is a low-pressure 11C-carbonylation technique that utilizes solvable xenon gas to effectively transfer and react [11C]carbon monoxide in a sealed reaction vessel. Both methods appear to be general and provide simple paths to 11C-labeled products.ConclusionRadiochemistry is the foundation of PET imaging which relies on the administration of a radiopharmaceutical. The demand for new radiopharmaceuticals for clinical PET imaging is increasing, and 11C-radiopharmaceuticals are especially important within clinical research and drug development. This review gives a comprehensive overview of the most noteworthy 11C-labeling methods with clinical relevance to the field of PET radiochemistry.

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“…[14][15][16][17][18] While 11 C-aminocarbonylation reactions are among the most common reactions with [ 11 C]CO, only a few labeled compounds bearing the N-[ 11 C]acrylamide functionality are known. [19][20][21] Despite hundreds of labeled compounds prepared, only four PET radiopharmaceuticals synthesized by [ 11 C] CO have been administered for human use, and all reported examples have relied on a high-pressure autoclave methodology. 14,18 11 C-carbonylations that can be executed at atmospheric pressure have emerged in recent years to trap [ 11 C]CO in small volume vessels, including chemical complexation, use of soluble carrier gases, and ex situ production of [ 11 C]CO. 17,18 Two recent reviews have concluded that the lack of commercially available synthesis modules for 11 C-carbonylations and Good Manufacturing Practice (GMP) production is among the most important challenges to overcome for dissemination of [ 11 C]CO chemistry to the wider community and is attributed to the reason that so few PET tracers synthesized from [ 11 C]CO have been translated to human subjects.…”

Section: Introductionmentioning

confidence: 99%

Radiosynthesis of a Bruton's tyrosine kinase inhibitor, [¹¹C]Tolebrutinib, via palladium‐NiXantphos‐mediated carbonylation

Dahl

Turner

Vasdev

2020

Labelled Comp Radiopharmac

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Bruton's tyrosine kinase (BTK) is a key component in the B‐cell receptor signaling pathway and is consequently a target for in vivo imaging of B‐cell malignancies as well as in multiple sclerosis (MS) with positron emission tomography (PET). A recent Phase 2b study with Sanofi's BTK inhibitor, Tolebrutinib (also known as [a.k.a.] SAR442168, PRN2246, or BTK'168) showed significantly reduced disease activity associated with MS. Herein, we report the radiosynthesis of [11C]Tolebrutinib ([11C]5) as a potential PET imaging agent for BTK. The N‐[11C]acrylamide moiety of [11C]5 was labeled by 11C‐carbonylation starting from [11C]CO, iodoethylene, and the secondary amine precursor via a novel palladium‐NiXantphos‐mediated carbonylation protocol, and the synthesis was fully automated using a commercial carbon‐11 synthesis platform (TracerMaker™, Scansys Laboratorieteknik). [11C]5 was obtained in a decay‐corrected radiochemical yield of 37 ± 2% (n = 5, relative to starting [11C]CO activity) in >99% radiochemical purity, with an average molar activity of 45 GBq/μmol (1200 mCi/μmol). We envision that this methodology will be generally applicable for the syntheses of labeled N‐acrylamides.

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Development of carbon-11 labeled acryl amides for selective PET imaging of active tissue transglutaminase

Cited by 30 publications

References 36 publications

¹¹CO bonds made easily for positron emission tomography radiopharmaceuticals

¹¹CO bonds made easily for positron emission tomography radiopharmaceuticals

New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals

Radiosynthesis of a Bruton's tyrosine kinase inhibitor, [¹¹C]Tolebrutinib, via palladium‐NiXantphos‐mediated carbonylation

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Development of carbon-11 labeled acryl amides for selective PET imaging of active tissue transglutaminase

Cited by 30 publications

References 36 publications

11CO bonds made easily for positron emission tomography radiopharmaceuticals

11CO bonds made easily for positron emission tomography radiopharmaceuticals

New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals

Radiosynthesis of a Bruton's tyrosine kinase inhibitor, [11C]Tolebrutinib, via palladium‐NiXantphos‐mediated carbonylation

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Product

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¹¹CO bonds made easily for positron emission tomography radiopharmaceuticals

¹¹CO bonds made easily for positron emission tomography radiopharmaceuticals

Radiosynthesis of a Bruton's tyrosine kinase inhibitor, [¹¹C]Tolebrutinib, via palladium‐NiXantphos‐mediated carbonylation