Literature DB >> 24900701

Discovery of MK-3168: A PET Tracer for Imaging Brain Fatty Acid Amide Hydrolase.

Ping Liu1, Terence G Hamill2, Marc Chioda1, Harry Chobanian1, Selena Fung1, Yan Guo1, Linda Chang1, Raman Bakshi1, Qingmei Hong1, James Dellureficio1, Linus S Lin1, Catherine Abbadie1, Jessica Alexander1, Hong Jin1, Suzanne Mandala1, Lin-Lin Shiao1, Wenping Li2, Sandra Sanabria2, David Williams2, Zhizhen Zeng2, Richard Hajdu1, Nina Jochnowitz1, Mark Rosenbach1, Bindhu Karanam1, Maria Madeira1, Gino Salituro1, Joyce Powell1, Ling Xu1, Jenna L Terebetski1, Joseph F Leone1, Patricia Miller2, Jacquelynn Cook2, Marie Holahan2, Aniket Joshi2, Stacey O'Malley2, Mona Purcell2, Diane Posavec2, Tsing-Bau Chen2, Kerry Riffel2, Mangay Williams2, Richard Hargreaves2, Kathleen A Sullivan1, Ravi P Nargund1, Robert J DeVita1.   

Abstract

We report herein the discovery of a fatty acid amide hydrolase (FAAH) positron emission tomography (PET) tracer. Starting from a pyrazole lead, medicinal chemistry efforts directed toward reducing lipophilicity led to the synthesis of a series of imidazole analogues. Compound 6 was chosen for further profiling due to its appropriate physical chemical properties and excellent FAAH inhibition potency across species. [(11)C]-6 (MK-3168) exhibited good brain uptake and FAAH-specific signal in rhesus monkeys and is a suitable PET tracer for imaging FAAH in the brain.

Entities:  

Keywords:  FAAH; Fatty acid amide hydrolase; PET tracer; biomarker; carbon-11; positron emission tomography; target engagement

Year:  2013        PMID： 24900701      PMCID： PMC4027136          DOI： 10.1021/ml4000996

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  25 in total

1.  Modulation of anxiety through blockade of anandamide hydrolysis.

Authors:  Satish Kathuria; Silvana Gaetani; Darren Fegley; Fernando Valiño; Andrea Duranti; Andrea Tontini; Marco Mor; Giorgio Tarzia; Giovanna La Rana; Antonio Calignano; Arcangela Giustino; Maria Tattoli; Maura Palmery; Vincenzo Cuomo; Daniele Piomelli
Journal:  Nat Med       Date:  2002-12-02       Impact factor: 53.440

2.  Biochemical characterization and in vitro activity of AZ513, a noncovalent, reversible, and noncompetitive inhibitor of fatty acid amide hydrolase.

Authors:  Clay W Scott; Gaochao Tian; Xiao Hong Yu; Kathy A Paschetto; Dee E Wilkins; Luc Meury; Chang Qing Cao; Jeffrey Varnes; Philip D Edwards
Journal:  Eur J Pharmacol       Date:  2011-06-01       Impact factor: 4.432

Review 3.  The fatty acid amide hydrolase (FAAH).

Authors:  N Ueda; R A Puffenbarger; S Yamamoto; D G Deutsch
Journal:  Chem Phys Lipids       Date:  2000-11       Impact factor: 3.329

4.  Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase.

Authors:  B F Cravatt; K Demarest; M P Patricelli; M H Bracey; D K Giang; B R Martin; A H Lichtman
Journal:  Proc Natl Acad Sci U S A       Date:  2001-07-24       Impact factor: 11.205

5.  [11C]CURB: Evaluation of a novel radiotracer for imaging fatty acid amide hydrolase by positron emission tomography.

Authors:  Alan A Wilson; Armando Garcia; Jun Parkes; Sylvain Houle; Junchao Tong; Neil Vasdev
Journal:  Nucl Med Biol       Date:  2011-02       Impact factor: 2.408

6.  Antidepressant-like activity and modulation of brain monoaminergic transmission by blockade of anandamide hydrolysis.

Authors:  G Gobbi; F R Bambico; R Mangieri; M Bortolato; P Campolongo; M Solinas; T Cassano; M G Morgese; G Debonnel; A Duranti; A Tontini; G Tarzia; M Mor; V Trezza; S R Goldberg; V Cuomo; D Piomelli
Journal:  Proc Natl Acad Sci U S A       Date:  2005-12-13       Impact factor: 11.205

Review 7.  The palmitoylethanolamide family: a new class of anti-inflammatory agents?

Authors:  Didier M Lambert; Severine Vandevoorde; Kent-Olov Jonsson; Christopher J Fowler
Journal:  Curr Med Chem       Date:  2002-03       Impact factor: 4.530

8.  An anorexic lipid mediator regulated by feeding.

Authors:  F Rodríguez de Fonseca; M Navarro; R Gómez; L Escuredo; F Nava; J Fu; E Murillo-Rodríguez; A Giuffrida; J LoVerme; S Gaetani; S Kathuria; C Gall; D Piomelli
Journal:  Nature       Date:  2001-11-08       Impact factor: 49.962

9.  Synthesis, in vitro and in vivo evaluation, and radiolabeling of aryl anandamide analogues as candidate radioligands for in vivo imaging of fatty acid amide hydrolase in the brain.

Authors:  Leonie Wyffels; Giulio G Muccioli; Sylvie De Bruyne; Lieselotte Moerman; Johan Sambre; Didier M Lambert; Filip De Vos
Journal:  J Med Chem       Date:  2009-08-13       Impact factor: 7.446

10.  Mice lacking fatty acid amide hydrolase exhibit a cannabinoid receptor-mediated phenotypic hypoalgesia.

Authors:  Aron H Lichtman; Christopher C Shelton; Tushar Advani; Benjamin F Cravatt
Journal:  Pain       Date:  2004-06       Impact factor: 6.961
View more
  14 in total

1.  Target and Tissue Selectivity Prediction by Integrated Mechanistic Pharmacokinetic-Target Binding and Quantitative Structure Activity Modeling.

Authors:  Anna H C Vlot; Wilhelmus E A de Witte; Meindert Danhof; Piet H van der Graaf; Gerard J P van Westen; Elizabeth C M de Lange
Journal:  AAPS J       Date:  2017-12-04       Impact factor: 4.009

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

Authors:  Justin W Hicks; Jun Parkes; Junchao Tong; Sylvain Houle; Neil Vasdev; Alan A Wilson
Journal:  Nucl Med Biol       Date:  2014-05-10       Impact factor: 2.408

3.  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

4.  Discovery of MK-4409, a Novel Oxazole FAAH Inhibitor for the Treatment of Inflammatory and Neuropathic Pain.

Authors:  Harry R Chobanian; Yan Guo; Ping Liu; Marc D Chioda; Selena Fung; Thomas J Lanza; Linda Chang; Raman K Bakshi; James P Dellureficio; Qingmei Hong; Mark McLaughlin; Kevin M Belyk; Shane W Krska; Amanda K Makarewicz; Elliot J Martel; Joseph F Leone; Lisa Frey; Bindhu Karanam; Maria Madeira; Raul Alvaro; Joyce Shuman; Gino Salituro; Jenna L Terebetski; Nina Jochnowitz; Shruti Mistry; Erin McGowan; Richard Hajdu; Mark Rosenbach; Catherine Abbadie; Jessica P Alexander; Lin-Lin Shiao; Kathleen M Sullivan; Ravi P Nargund; Matthew J Wyvratt; Linus S Lin; Robert J DeVita
Journal:  ACS Med Chem Lett       Date:  2014-04-10       Impact factor: 4.345

5.  Synthesis and Preliminary PET Imaging Studies of a FAAH Radiotracer ([¹¹C]MPPO) Based on α-Ketoheterocyclic Scaffold.

Authors:  Lu Wang; Joji Yui; Qifan Wang; Yiding Zhang; Wakana Mori; Yoko Shimoda; Masayuki Fujinaga; Katsushi Kumata; Tomoteru Yamasaki; Akiko Hatori; Benjamin H Rotstein; Thomas Lee Collier; Chongzhao Ran; Neil Vasdev; Ming-Rong Zhang; Steven H Liang
Journal:  ACS Chem Neurosci       Date:  2015-11-17       Impact factor: 4.418

6.  Discovery of carbon-11 labeled sulfonamide derivative: A PET tracer for imaging brain NLRP3 inflammasome.

Authors:  Yulong Xu; Yiming Xu; Hallie Blevins; Yu Lan; Yan Liu; Gengyang Yuan; Robin Striar; Julia S Zagaroli; Darcy R Tocci; Amelia G Langan; Can Zhang; Shijun Zhang; Changning Wang
Journal:  Bioorg Med Chem Lett       Date:  2021-01-06       Impact factor: 2.823

Review 7.  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

Review 8.  Molecular Imaging of Hydrolytic Enzymes Using PET and SPECT.

Authors:  Brian P Rempel; Eric W Price; Christopher P Phenix
Journal:  Mol Imaging       Date:  2017 Jan-Dec       Impact factor: 4.488

9.  Fatty Acid Amide Hydrolase Inhibition by JNJ-42165279: A Multiple-Ascending Dose and a Positron Emission Tomography Study in Healthy Volunteers.

Authors:  Andrey Postnov; Mark E Schmidt; Darrel J Pemberton; Jan de Hoon; Anne van Hecken; Maarten van den Boer; Peter Zannikos; Peter van der Ark; James A Palmer; Stef Rassnick; Sofie Celen; Guy Bormans; Koen van Laere
Journal:  Clin Transl Sci       Date:  2018-03-25       Impact factor: 4.689

10.  PET imaging of fatty acid amide hydrolase with [(18)F]DOPP in nonhuman primates.

Authors:  Benjamin H Rotstein; Hsiao-Ying Wey; Timothy M Shoup; Alan A Wilson; Steven H Liang; Jacob M Hooker; Neil Vasdev
Journal:  Mol Pharm       Date:  2014-07-16       Impact factor: 4.939
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.