Synthesis and Preclinical Evaluation of Sulfonamido-based [11C-Carbonyl]-Carbamates and Ureas for Imaging Monoacylglycerol Lipase Article Swipe
Lu Wang
,
Wakana Mori
,
Ran Cheng
,
Joji Yui
,
Akiko Hatori
,
Longle Ma
,
Yiding Zhang
,
Benjamin H. Rotstein
,
Masayuki Fujinaga
,
Yoko Shimoda
,
Tomoteru Yamasaki
,
Lin Xie
,
Yuji Nagai
,
Takafumi Minamimoto
,
Makoto Higuchi
,
Neil Vasdev
,
Ming‐Rong Zhang
,
Steven H. Liang
·
YOU?
·
· 2016
· Open Access
·
· DOI: https://doi.org/10.7150/thno.15257
YOU?
·
· 2016
· Open Access
·
· DOI: https://doi.org/10.7150/thno.15257
Monoacylglycerol lipase (MAGL) is a 33 kDa member of the serine hydrolase superfamily that preferentially degrades 2-arachidonoylglycerol (2-AG) to arachidonic acid in the endocannabinoid system. Inhibition of MAGL is not only of interest for probing the cannabinoid pathway but also as a therapeutic and diagnostic target for neuroinflammation. Limited attempts have been made to image MAGL in vivo and a suitable PET ligand for this target has yet to be identified and is urgently sought to guide small molecule drug development in this pathway. Herein we synthesized and evaluated the physiochemical properties of an array of eleven sulfonamido-based carbamates and ureas with a series of terminal aryl moieties, linkers and leaving groups. The most potent compounds were a novel MAGL inhibitor, N-((1-(1H-1,2,4-triazole-1-carbonyl)piperidin-4-yl) methyl)-4-chlorobenzenesulfonamide (TZPU; IC50 = 35.9 nM), and the known inhibitor 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(((4-chlorophenyl)sulfonamido) methyl)piperidine-1-carboxylate (SAR127303; IC50 = 39.3 nM), which were also shown to be selective for MAGL over fatty acid amide hydrolase (FAAH), and cannabinoid receptors (CB1 & CB2). Both of these compounds were radiolabeled with carbon-11 via [(11)C]COCl2, followed by comprehensive ex vivo biodistribution and in vivo PET imaging studies in normal rats to determine their brain permeability, specificity, clearance and metabolism. Whereas TZPU did not show adequate specificity to warrant further evaluation, [(11)C]SAR127303 was advanced for preliminary PET neuroimaging studies in nonhuman primate. The tracer showed good brain permeability (ca. 1 SUV) and heterogeneous regional brain distribution which is consistent with the distribution of MAGL.
Related Topics
Concepts
Monoacylglycerol lipase
Fatty acid amide hydrolase
Chemistry
Endocannabinoid system
Serine hydrolase
Cannabinoid
Cannabinoid receptor
Biodistribution
In vivo
Pharmacology
Phosphomolybdic acid
Biochemistry
Ligand (biochemistry)
Stereochemistry
Enzyme
Serine
Receptor
Antagonist
In vitro
Medicine
Biology
Biotechnology
Catalysis
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.7150/thno.15257
- OA Status
- gold
- Cited By
- 55
- References
- 45
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W2415867517
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
-
https://openalex.org/W2415867517Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.7150/thno.15257Digital Object Identifier
- Title
-
Synthesis and Preclinical Evaluation of Sulfonamido-based [11C-Carbonyl]-Carbamates and Ureas for Imaging Monoacylglycerol LipaseWork title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2016Year of publication
- Publication date
-
2016-01-01Full publication date if available
- Authors
-
Lu Wang, Wakana Mori, Ran Cheng, Joji Yui, Akiko Hatori, Longle Ma, Yiding Zhang, Benjamin H. Rotstein, Masayuki Fujinaga, Yoko Shimoda, Tomoteru Yamasaki, Lin Xie, Yuji Nagai, Takafumi Minamimoto, Makoto Higuchi, Neil Vasdev, Ming‐Rong Zhang, Steven H. LiangList of authors in order
- Landing page
-
https://doi.org/10.7150/thno.15257Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
-
goldOpen access status per OpenAlex
- OA URL
-
https://doi.org/10.7150/thno.15257Direct OA link when available
- Concepts
-
Monoacylglycerol lipase, Fatty acid amide hydrolase, Chemistry, Endocannabinoid system, Serine hydrolase, Cannabinoid, Cannabinoid receptor, Biodistribution, In vivo, Pharmacology, Phosphomolybdic acid, Biochemistry, Ligand (biochemistry), Stereochemistry, Enzyme, Serine, Receptor, Antagonist, In vitro, Medicine, Biology, Biotechnology, CatalysisTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
55Total citation count in OpenAlex
- Citations by year (recent)
-
2025: 5, 2024: 2, 2023: 4, 2022: 13, 2021: 3Per-year citation counts (last 5 years)
- References (count)
-
45Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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