Literature DB >> 31518130

Design, Synthesis, and Evaluation of 18F-Labeled Monoacylglycerol Lipase Inhibitors as Novel Positron Emission Tomography Probes.

Zhen Chen1,2, Wakana Mori3, Hualong Fu1, Michael A Schafroth4, Akiko Hatori3, Tuo Shao1, Genwei Zhang5, Richard S Van5, Yiding Zhang3, Kuan Hu3, Masayuki Fujinaga3, Lu Wang1,6, Vasily Belov1,7, Daisuke Ogasawara4, Pilar Giffenig1,7, Xiaoyun Deng1, Jian Rong1, Qingzhen Yu1, Xiaofei Zhang1, Mikhail I Papisov1,7, Yihan Shao5, Thomas L Collier1, Jun-An Ma2, Benjamin F Cravatt4, Lee Josephson1, Ming-Rong Zhang3, Steven H Liang1.   

Abstract

Dysfunction of monoacylglycerol lipase (MAGL) is associated with several psychopathological disorders, including drug addiction and neurodegenerative diseases. Herein we design, synthesize, and evaluate several irreversible fluorine-containing MAGL inhibitors for positron emission tomography (PET) ligand development. Compound 6 (identified from a therapeutic agent) was advanced for 18F-labeling via a novel spirocyclic iodonium ylide (SCIDY) strategy, which demonstrated high brain permeability and excellent specific binding. This work supports further development of novel 18F-labeled MAGL PET probes.

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Year:  2019        PMID： 31518130      PMCID： PMC7875603          DOI： 10.1021/acs.jmedchem.9b00936

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  29 in total

Review 1.  The molecular logic of endocannabinoid signalling.

Authors:  Daniele Piomelli
Journal:  Nat Rev Neurosci       Date:  2003-11       Impact factor: 34.870

Review 2.  Molecular imaging in drug development.

Authors:  Jürgen K Willmann; Nicholas van Bruggen; Ludger M Dinkelborg; Sanjiv S Gambhir
Journal:  Nat Rev Drug Discov       Date:  2008-07       Impact factor: 84.694

3.  Brain regional cannabinoid CB(1) receptor signalling and alternative enzymatic pathways for 2-arachidonoylglycerol generation in brain sections of diacylglycerol lipase deficient mice.

Authors:  Niina Aaltonen; Casandra Riera Ribas; Marko Lehtonen; Juha R Savinainen; Jarmo T Laitinen
Journal:  Eur J Pharm Sci       Date:  2013-09-03       Impact factor: 4.384

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

Authors:  Muneer Ahamed; Bala Attili; Daisy van Veghel; Maarten Ooms; Philippe Berben; Sofie Celen; Michel Koole; Lieven Declercq; Juha R Savinainen; Jarmo T Laitinen; Alfons Verbruggen; Guy Bormans
Journal:  Eur J Med Chem       Date:  2017-04-25       Impact factor: 6.514

5.  Design, Synthesis, and Evaluation of Reversible and Irreversible Monoacylglycerol Lipase Positron Emission Tomography (PET) Tracers Using a "Tail Switching" Strategy on a Piperazinyl Azetidine Skeleton.

Authors:  Zhen Chen; Wakana Mori; Xiaoyun Deng; Ran Cheng; Daisuke Ogasawara; Genwei Zhang; Michael A Schafroth; Kenneth Dahl; Hualong Fu; Akiko Hatori; Tuo Shao; Yiding Zhang; Tomoteru Yamasaki; Xiaofei Zhang; Jian Rong; Qingzhen Yu; Kuan Hu; Masayuki Fujinaga; Lin Xie; Katsushi Kumata; Yuancheng Gou; Jingjin Chen; Shuyin Gu; Liang Bao; Lu Wang; Thomas Lee Collier; Neil Vasdev; Yihan Shao; Jun-An Ma; Benjamin F Cravatt; Christopher Fowler; Lee Josephson; Ming-Rong Zhang; Steven H Liang
Journal:  J Med Chem       Date:  2019-03-21       Impact factor: 7.446

6.  A second endogenous cannabinoid that modulates long-term potentiation.

Authors:  N Stella; P Schweitzer; D Piomelli
Journal:  Nature       Date:  1997-08-21       Impact factor: 49.962

7.  Crystal structure of a soluble form of human monoglyceride lipase in complex with an inhibitor at 1.35 Å resolution.

Authors:  Céline Schalk-Hihi; Carsten Schubert; Richard Alexander; Shariff Bayoumy; Jose C Clemente; Ingrid Deckman; Renee L DesJarlais; Keli C Dzordzorme; Christopher M Flores; Bruce Grasberger; James K Kranz; Frank Lewandowski; Li Liu; Hongchang Ma; Diane Maguire; Mark J Macielag; Mark E McDonnell; Tara Mezzasalma Haarlander; Robyn Miller; Cindy Milligan; Charles Reynolds; Lawrence C Kuo
Journal:  Protein Sci       Date:  2011-03-01       Impact factor: 6.725

Review 8.  Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents.

Authors:  Rikki N Waterhouse
Journal:  Mol Imaging Biol       Date:  2003 Nov-Dec       Impact factor: 3.488

9.  In Vitro and in Vivo Evaluation of 11C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies.

Authors:  Ran Cheng; Wakana Mori; Longle Ma; Mireille Alhouayek; Akiko Hatori; Yiding Zhang; Daisuke Ogasawara; Gengyang Yuan; Zhen Chen; Xiaofei Zhang; Hang Shi; Tomoteru Yamasaki; Lin Xie; Katsushi Kumata; Masayuki Fujinaga; Yuji Nagai; Takafumi Minamimoto; Mona Svensson; Lu Wang; Yunfei Du; Mary Jo Ondrechen; Neil Vasdev; Benjamin F Cravatt; Christopher Fowler; Ming-Rong Zhang; Steven H Liang
Journal:  J Med Chem       Date:  2018-03-09       Impact factor: 7.446

10.  Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.

Authors:  R Mechoulam; S Ben-Shabat; L Hanus; M Ligumsky; N E Kaminski; A R Schatz; A Gopher; S Almog; B R Martin; D R Compton
Journal:  Biochem Pharmacol       Date:  1995-06-29       Impact factor: 5.858
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  5 in total

1.  In Vivo Imaging of the Tumor-Associated Enzyme NCEH1 with a Covalent PET Probe.

Authors:  Jae Won Chang; Mohammed Bhuiyan; Hsiu-Ming Tsai; Hannah J Zhang; Gang Li; Shaghayegh Fathi; David C McCutcheon; Lara Leoni; Richard Freifelder; Chin-Tu Chen; Raymond E Moellering
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-15       Impact factor: 15.336

Review 2.  Positron Emission Tomography Imaging of the Endocannabinoid System: Opportunities and Challenges in Radiotracer Development.

Authors:  Lu Hou; Jian Rong; Ahmed Haider; Daisuke Ogasawara; Cassis Varlow; Michael A Schafroth; Linjing Mu; Jiefeng Gan; Hao Xu; Christopher J Fowler; Ming-Rong Zhang; Neil Vasdev; Simon Ametamey; Benjamin F Cravatt; Lu Wang; Steven H Liang
Journal:  J Med Chem       Date:  2020-12-30       Impact factor: 7.446

3.  Novel Reversible-Binding PET Ligands for Imaging Monoacylglycerol Lipase Based on the Piperazinyl Azetidine Scaffold.

Authors:  Jian Rong; Wakana Mori; Xiaotian Xia; Michael A Schafroth; Chunyu Zhao; Richard S Van; Tomoteru Yamasaki; Jiahui Chen; Zhiwei Xiao; Ahmed Haider; Daisuke Ogasawara; Atsuto Hiraishi; Tuo Shao; Yiding Zhang; Zhen Chen; Fuwen Pang; Kuan Hu; Lin Xie; Masayuki Fujinaga; Katsushi Kumata; Yuancheng Gou; Yang Fang; Shuyin Gu; Huiyi Wei; Liang Bao; Hao Xu; Thomas L Collier; Yihan Shao; Richard E Carson; Benjamin F Cravatt; Lu Wang; Ming-Rong Zhang; Steven H Liang
Journal:  J Med Chem       Date:  2021-09-27       Impact factor: 8.039

Review 4.  Enzymatic synthesis of fluorinated compounds.

Authors:  Xinkuan Cheng; Long Ma
Journal:  Appl Microbiol Biotechnol       Date:  2021-10-09       Impact factor: 4.813

5.  Development of a highly-specific 18F-labeled irreversible positron emission tomography tracer for monoacylglycerol lipase mapping.

Authors:  Zhen Chen; Wakana Mori; Jian Rong; Michael A Schafroth; Tuo Shao; Richard S Van; Daisuke Ogasawara; Tomoteru Yamasaki; Atsuto Hiraishi; Akiko Hatori; Jiahui Chen; Yiding Zhang; Kuan Hu; Masayuki Fujinaga; Jiyun Sun; Qingzhen Yu; Thomas L Collier; Yihan Shao; Benjamin F Cravatt; Lee Josephson; Ming-Rong Zhang; Steven H Liang
Journal:  Acta Pharm Sin B       Date:  2021-04-01       Impact factor: 11.413
  5 in total

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