Radiosynthesis and ex vivo evaluation of [11C-carbonyl]carbamate- and urea-based monoacylglycerol lipase inhibitors

Hicks, Justin; Parkes, Jun; Tong, Junchao; Houle, Sylvain; Vasdev, Neil; Wilson, Alan A.

doi:10.1016/j.nucmedbio.2014.05.001

Cited by 33 publications

(37 citation statements)

References 41 publications

(75 reference statements)

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“…43 A wide variety of alcohols, including hindered and electron-deficient ones such as tert -butanol, and hexafluoroisopropanol 52 have been successfully incorporated into 11 C-carbamates by this method. Using amino alcohol precursors for [ 11 C]CO 2 -fixation, oxazolidinones are formed at ambient temperature after dehydration with POCl 3 .…”

Section: [11c]co2-fixationmentioning

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]co2-fixationmentioning

confidence: 99%

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

et al. 2016

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“…Hicks and co-workers reported PET radioligands for imaging of MAGL [26]. In this study, we modified the structure of JW642 in which the phenoxy group is substituted with a methoxy group resulting in MA-PB-1.…”

Section: Structures Of Recently Reported Magl Pet Tracers and Of Ma-pmentioning

confidence: 99%

Synthesis and preclinical evaluation of [ 11 C]MA-PB-1 for in vivo imaging of brain monoacylglycerol lipase (MAGL)

Ahamed

Attili

Veghel

et al. 2017

European Journal of Medicinal Chemistry

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MAGL is a potential therapeutic target for oncological and psychiatric diseases. Our objective was to develop a PET tracer for in vivo quantification of MAGL. We report [C]MA-PB-1 as an irreversible MAGL inhibitor PET tracer. The in vitro inhibitory activity, ex vivo distribution, brain kinetics and specificity of [C]MA-PB-1 binding were studied. Ex vivo biodistribution and microPET showed good brain uptake which could be blocked by pretreatment with both MA-PB-1 and a structurally non-related MAGL inhibitor MJN110. These initial results suggest that [C]MA-PB-1 is a suitable tracer for in vivo imaging of MAGL.

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“…1) by Lambert and co-workers 16 and piperazine ureas (e.g., 60j) by Kono et al 17,18 While writing this manuscript, Wilson and co-workers have reported radiosynthesis of carbamate-and urea-based MAGL inhibitors. 19 In this work, we follow up our previous study, in which we have designed and characterized piperazine and piperidine triazole ureas as highly potent and MAGL-selective inhibitors culminating in the synthesis of JJKK-048, which appeared the most potent and MAGL selective inhibitor currently described (IC 50 < 0.4 nM). 20 Here, we describe the further optimization of piperazine and piperidine carboxamides and carbamates as potent and selective MAGL/ FAAH inhibitors or as dual FAAH/MAGL inhibitors.…”

Section: Introductionmentioning

confidence: 95%

Piperazine and piperidine carboxamides and carbamates as inhibitors of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL)

Korhonen

Kuusisto

Bruchem

et al. 2014

Bioorganic & Medicinal Chemistry

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Radiosynthesis and ex vivo evaluation of [11C-carbonyl]carbamate- and urea-based monoacylglycerol lipase inhibitors

Cited by 33 publications

References 41 publications

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

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

Synthesis and preclinical evaluation of [ 11 C]MA-PB-1 for in vivo imaging of brain monoacylglycerol lipase (MAGL)

Piperazine and piperidine carboxamides and carbamates as inhibitors of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL)

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Radiosynthesis and ex vivo evaluation of [11C-carbonyl]carbamate- and urea-based monoacylglycerol lipase inhibitors

Cited by 33 publications

References 41 publications

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

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

Synthesis and preclinical evaluation of [ 11 C]MA-PB-1 for in vivo imaging of brain monoacylglycerol lipase (MAGL)

Piperazine and piperidine carboxamides and carbamates as inhibitors of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL)

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

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