Literature DB >> 21855337

Design and evaluation of a novel fluorescent CB2 ligand as probe for receptor visualization in immune cells.

Ravil R Petrov1, Maria E Ferrini, Zeina Jaffar, Charles M Thompson, Kevan Roberts, Philippe Diaz.   

Abstract

Cannabinoid CB2 receptor has emerged as a very promising target over the last decades. We have synthesized and evaluated a new fluorescent probe designated NMP6 based on 6-methoxyisatin scaffold, which exhibited selectivity and K(i) value at hCB2 of 387 nM. We have demonstrated its ability to be an effective probe for visualization of CB2 receptor binding using confocal microscopy and a flow cytometry probe for the analysis of CB2 protein expression. Furthermore, NMP6 was easily obtained in two chemical steps from commercially available building blocks.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 21855337      PMCID: PMC3171627          DOI: 10.1016/j.bmcl.2011.07.099

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  32 in total

1.  Chemical modification of the naphthoyl 3-position of JWH-015: in search of a fluorescent probe to the cannabinoid CB2 receptor.

Authors:  Andrew S Yates; Stephen W Doughty; David A Kendall; Barrie Kellam
Journal:  Bioorg Med Chem Lett       Date:  2005-08-15       Impact factor: 2.823

Review 2.  The (endo)cannabinoid system in multiple sclerosis and amyotrophic lateral sclerosis.

Authors:  Diego Centonze; Silvia Rossi; Alessandro Finazzi-Agrò; Giorgio Bernardi; Mauro Maccarrone
Journal:  Int Rev Neurobiol       Date:  2007       Impact factor: 3.230

3.  MBC94, a conjugable ligand for cannabinoid CB 2 receptor imaging.

Authors:  Mingfeng Bai; Michelle Sexton; Nephi Stella; Darryl J Bornhop
Journal:  Bioconjug Chem       Date:  2008-04-30       Impact factor: 4.774

Review 4.  Discovery of the presence and functional expression of cannabinoid CB2 receptors in brain.

Authors:  Emmanuel S Onaivi; Hiroki Ishiguro; Jian-Ping Gong; Sejal Patel; Alex Perchuk; Paul A Meozzi; Lester Myers; Zoila Mora; Patricia Tagliaferro; Eileen Gardner; Alicia Brusco; Babatunde E Akinshola; Qing-Rong Liu; Bruce Hope; Shinya Iwasaki; Tadao Arinami; Lindsey Teasenfitz; George R Uhl
Journal:  Ann N Y Acad Sci       Date:  2006-08       Impact factor: 5.691

5.  Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain.

Authors:  Gerard M P Giblin; Celestine T O'Shaughnessy; Alan Naylor; William L Mitchell; Andrew J Eatherton; Brian P Slingsby; D Anthony Rawlings; Paul Goldsmith; Andrew J Brown; Carl P Haslam; Nick M Clayton; Alex W Wilson; Iain P Chessell; Andrew R Wittington; Richard Green
Journal:  J Med Chem       Date:  2007-05-04       Impact factor: 7.446

6.  Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain.

Authors:  Philippe Diaz; Jijun Xu; Fanny Astruc-Diaz; Hao-Min Pan; David L Brown; Mohamed Naguib
Journal:  J Med Chem       Date:  2008-07-31       Impact factor: 7.446

7.  MDA7: a novel selective agonist for CB2 receptors that prevents allodynia in rat neuropathic pain models.

Authors:  M Naguib; P Diaz; J J Xu; F Astruc-Diaz; S Craig; P Vivas-Mejia; D L Brown
Journal:  Br J Pharmacol       Date:  2008-09-01       Impact factor: 8.739

8.  Induction of CB2 receptor expression in the rat spinal cord of neuropathic but not inflammatory chronic pain models.

Authors:  Ji Zhang; Cyrla Hoffert; Huy Khang Vu; Thierry Groblewski; Sultan Ahmad; Dajan O'Donnell
Journal:  Eur J Neurosci       Date:  2003-06       Impact factor: 3.386

9.  6-Methoxy-N-alkyl isatin acylhydrazone derivatives as a novel series of potent selective cannabinoid receptor 2 inverse agonists: design, synthesis, and binding mode prediction.

Authors:  Philippe Diaz; Sharangdhar S Phatak; Jijun Xu; Fanny Astruc-Diaz; Claudio N Cavasotto; Mohamed Naguib
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446

10.  Cannabinoid receptor 2 is increased in acutely and chronically inflamed bladder of rats.

Authors:  Fabiola Voznika Merriam; Zun-yi Wang; Simone Domit Guerios; Dale E Bjorling
Journal:  Neurosci Lett       Date:  2008-08-31       Impact factor: 3.046

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  7 in total

Review 1.  The evolving small-molecule fluorescent-conjugate toolbox for Class A GPCRs.

Authors:  Andrea J Vernall; Stephen J Hill; Barrie Kellam
Journal:  Br J Pharmacol       Date:  2014-03       Impact factor: 8.739

Review 2.  Fluorescent approaches for understanding interactions of ligands with G protein coupled receptors.

Authors:  Rajashri Sridharan; Jeffrey Zuber; Sara M Connelly; Elizabeth Mathew; Mark E Dumont
Journal:  Biochim Biophys Acta       Date:  2013-09-18

3.  Detection of cannabinoid receptor type 2 in native cells and zebrafish with a highly potent, cell-permeable fluorescent probe.

Authors:  Thais Gazzi; Benjamin Brennecke; Kenneth Atz; Claudia Korn; David Sykes; Gabriel Forn-Cuni; Patrick Pfaff; Roman C Sarott; Matthias V Westphal; Yelena Mostinski; Leonard Mach; Malgorzata Wasinska-Kalwa; Marie Weise; Bradley L Hoare; Tamara Miljuš; Maira Mexi; Nicolas Roth; Eline J Koers; Wolfgang Guba; André Alker; Arne C Rufer; Eric A Kusznir; Sylwia Huber; Catarina Raposo; Elisabeth A Zirwes; Anja Osterwald; Anto Pavlovic; Svenja Moes; Jennifer Beck; Matthias Nettekoven; Irene Benito-Cuesta; Teresa Grande; Faye Drawnel; Gabriella Widmer; Daniela Holzer; Tom van der Wel; Harpreet Mandhair; Michael Honer; Jürgen Fingerle; Jörg Scheffel; Johannes Broichhagen; Klaus Gawrisch; Julián Romero; Cecilia J Hillard; Zoltan V Varga; Mario van der Stelt; Pal Pacher; Jürg Gertsch; Christoph Ullmer; Peter J McCormick; Sergio Oddi; Herman P Spaink; Mauro Maccarrone; Dmitry B Veprintsev; Erick M Carreira; Uwe Grether; Marc Nazaré
Journal:  Chem Sci       Date:  2022-04-01       Impact factor: 9.969

Review 4.  The CB2 receptor and its role as a regulator of inflammation.

Authors:  Caroline Turcotte; Marie-Renée Blanchet; Michel Laviolette; Nicolas Flamand
Journal:  Cell Mol Life Sci       Date:  2016-07-11       Impact factor: 9.261

5.  Selective Photoaffinity Probe That Enables Assessment of Cannabinoid CB2 Receptor Expression and Ligand Engagement in Human Cells.

Authors:  Marjolein Soethoudt; Sara C Stolze; Matthias V Westphal; Luuk van Stralen; Andrea Martella; Eva J van Rooden; Wolfgang Guba; Zoltan V Varga; Hui Deng; Sander I van Kasteren; Uwe Grether; Adriaan P IJzerman; Pal Pacher; Erick M Carreira; Herman S Overkleeft; Andreea Ioan-Facsinay; Laura H Heitman; Mario van der Stelt
Journal:  J Am Chem Soc       Date:  2018-02-16       Impact factor: 15.419

Review 6.  Functionalized Cannabinoid Subtype 2 Receptor Ligands: Fluorescent, PET, Photochromic and Covalent Molecular Probes.

Authors:  Filippo Basagni; Michela Rosini; Michael Decker
Journal:  ChemMedChem       Date:  2020-06-24       Impact factor: 3.466

Review 7.  Detection of genome-edited and endogenously expressed G protein-coupled receptors.

Authors:  Mark Soave; Leigh A Stoddart; Carl W White; Laura E Kilpatrick; Joëlle Goulding; Stephen J Briddon; Stephen J Hill
Journal:  FEBS J       Date:  2021-02-09       Impact factor: 5.542

  7 in total

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