Synthesis and biological evaluation of indole-2-carboxamides bearing photoactivatable functionalities as novel allosteric modulators for the cannabinoid CB1 receptor.

[1]  G. Thakur,et al.  Mapping Cannabinoid 1 Receptor Allosteric Site(s): Critical Molecular Determinant and Signaling Profile of GAT100, a Novel, Potent, and Irreversibly Binding Probe. , 2016, ACS chemical neuroscience.

[2]  A. Makriyannis,et al.  Novel Electrophilic and Photoaffinity Covalent Probes for Mapping the Cannabinoid 1 Receptor Allosteric Site(s) , 2015, Journal of medicinal chemistry.

[3]  D. Farrens,et al.  Structural dynamics and energetics underlying allosteric inactivation of the cannabinoid receptor CB1 , 2015, Proceedings of the National Academy of Sciences.

[4]  A. Lichtman,et al.  A Cannabinoid CB1 Receptor-Positive Allosteric Modulator Reduces Neuropathic Pain in the Mouse with No Psychoactive Effects , 2015, Neuropsychopharmacology.

[5]  T. Kenakin,et al.  Structure-activity relationships of substituted 1H-indole-2-carboxamides as CB1 receptor allosteric modulators. , 2015, Bioorganic & medicinal chemistry.

[6]  Y. Hashidoko,et al.  Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling. , 2015, Organic letters.

[7]  L. Jing,et al.  Effects of the cannabinoid CB₁ receptor allosteric modulator ORG 27569 on reinstatement of cocaine- and methamphetamine-seeking behavior in rats. , 2014, Drug and alcohol dependence.

[8]  P. Sexton,et al.  Development of a photoactivatable allosteric ligand for the m1 muscarinic acetylcholine receptor. , 2014, ACS chemical neuroscience.

[9]  Hamed I. Ali,et al.  Optimization of Chemical Functionalities of Indole-2-carboxamides To Improve Allosteric Parameters for the Cannabinoid Receptor 1 (CB1) , 2014, Journal of medicinal chemistry.

[10]  Derek M. Shore,et al.  Allosteric Modulation of a Cannabinoid G Protein-coupled Receptor , 2013, The Journal of Biological Chemistry.

[11]  Hamed I. Ali,et al.  Structure-activity relationship study of indole-2-carboxamides identifies a potent allosteric modulator for the cannabinoid receptor 1 (CB1). , 2013, Journal of medicinal chemistry.

[12]  S. Iwata,et al.  Synthesis of Photoreactive 2‐Phenethylamine Derivatives – Synthesis of Adenosine Derivatives Enabling Functional Analysis of Adenosine Receptors by Photoaffinity Labeling , 2013 .

[13]  M. Mahmoud,et al.  Profiling two indole‐2‐carboxamides for allosteric modulation of the CB1 receptor , 2013, Journal of neurochemistry.

[14]  K. Bales,et al.  γ-Secretase Modulator (GSM) Photoaffinity Probes Reveal Distinct Allosteric Binding Sites on Presenilin* , 2013, The Journal of Biological Chemistry.

[15]  D. Bolognini,et al.  CB1 Receptor Allosteric Modulators Display Both Agonist and Signaling Pathway Specificity , 2013, Molecular Pharmacology.

[16]  R. N. Takahashi,et al.  Anti-inflammatory lipoxin A4 is an endogenous allosteric enhancer of CB1 cannabinoid receptor , 2012, Proceedings of the National Academy of Sciences.

[17]  Y. Hashidoko,et al.  Comprehensive synthesis of photoreactive (3-trifluoromethyl)diazirinyl indole derivatives from 5- and 6- trifluoroacetylindoles for photoaffinity labeling. , 2012, The Journal of organic chemistry.

[18]  B. Lutz,et al.  Identification and Quantification of a New Family of Peptide Endocannabinoids (Pepcans) Showing Negative Allosteric Modulation at CB1 Receptors* , 2012, The Journal of Biological Chemistry.

[19]  Younis Baqi,et al.  Allosteric modulators of rhodopsin-like G protein-coupled receptors: opportunities in drug development. , 2012, Pharmacology & therapeutics.

[20]  D. Farrens,et al.  A Key Agonist-induced Conformational Change in the Cannabinoid Receptor CB1 Is Blocked by the Allosteric Ligand Org 27569* , 2012, The Journal of Biological Chemistry.

[21]  N. Stergiopulos,et al.  The activation of the cannabinoid receptor type 2 reduces neutrophilic protease-mediated vulnerability in atherosclerotic plaques. , 2012, European heart journal.

[22]  K. Ahn,et al.  Allosteric Modulator ORG27569 Induces CB1 Cannabinoid Receptor High Affinity Agonist Binding State, Receptor Internalization, and Gi Protein-independent ERK1/2 Kinase Activation* , 2012, The Journal of Biological Chemistry.

[23]  A. Makriyannis,et al.  Mass spectrometry-based proteomics of human cannabinoid receptor 2: covalent cysteine 6.47(257)-ligand interaction affording megagonist receptor activation. , 2011, Journal of proteome research.

[24]  Jonathan B. Cohen,et al.  Multiple Transmembrane Binding Sites for p-Trifluoromethyldiazirinyl-etomidate, a Photoreactive Torpedo Nicotinic Acetylcholine Receptor Allosteric Inhibitor* , 2011, The Journal of Biological Chemistry.

[25]  A. Makriyannis,et al.  Mass spectrometry-based GPCR proteomics: comprehensive characterization of the human cannabinoid 1 receptor. , 2010, Journal of proteome research.

[26]  Emmanuel Baslé,et al.  Protein chemical modification on endogenous amino acids. , 2010, Chemistry & biology.

[27]  J. L. Howard,et al.  Positive allosteric modulation of the human cannabinoid (CB1) receptor by RTI‐371, a selective inhibitor of the dopamine transporter , 2009, British journal of pharmacology.

[28]  S. Goldberg,et al.  The future of endocannabinoid-oriented clinical research after CB1 antagonists , 2009, Psychopharmacology.

[29]  Arthur Christopoulos,et al.  Allosteric modulators of GPCRs: a novel approach for the treatment of CNS disorders , 2009, Nature Reviews Drug Discovery.

[30]  Y. Mostafa,et al.  Synthesis and Biological Activity of Functionalized Indole‐2‐carboxylates, Triazino‐ and Pyridazino‐indoles , 2008, Archiv der Pharmazie.

[31]  C. Reynet,et al.  PSNCBAM‐1, a novel allosteric antagonist at cannabinoid CB1 receptors with hypophagic effects in rats , 2007, British journal of pharmacology.

[32]  P. Pacher,et al.  The Endocannabinoid System as an Emerging Target of Pharmacotherapy , 2006, Pharmacological Reviews.

[33]  K. Tomer,et al.  Photoaffinity labeling combined with mass spectrometric approaches as a tool for structural proteomics , 2006, Expert review of proteomics.

[34]  R. Mishra,et al.  Design and synthesis of photoaffinity-labeling ligands of the L-prolyl-L-leucylglycinamide binding site involved in the allosteric modulation of the dopamine receptor. , 2006, Journal of medicinal chemistry.

[35]  U. Madsen,et al.  Rapid Synthesis of Aryl Azides from Aryl Halides under Mild Conditions. , 2005 .

[36]  Ken Mackie,et al.  Cannabinoid receptors as therapeutic targets. , 2006, Annual review of pharmacology and toxicology.

[37]  R. Pertwee.  Cannabinoid pharmacology: the first 66 years , 2006, British journal of pharmacology.

[38]  A. Christopoulos,et al.  Allosteric Modulation of the Cannabinoid CB1 Receptor , 2005, Molecular Pharmacology.

[39]  A. Makriyannis,et al.  High affinity electrophilic and photoactivatable covalent endocannabinoid probes for the CB1 receptor. , 2005, Journal of medicinal chemistry.

[40]  Stefan Bräse,et al.  Organic azides: an exploding diversity of a unique class of compounds. , 2005, Angewandte Chemie.

[41]  D. C. Chiara,et al.  Gating-enhanced Accessibility of Hydrophobic Sites within the Transmembrane Region of the Nicotinic Acetylcholine Receptor's δ-Subunit , 2005, Journal of Biological Chemistry.

[42]  K. Mackie,et al.  Distribution of cannabinoid receptors in the central and peripheral nervous system. , 2005, Handbook of experimental pharmacology.

[43]  R. Hampson,et al.  Cannabinoid physiology and pharmacology: 30 years of progress , 2004, Neuropharmacology.

[44]  L. Petrocellis,et al.  The endocannabinoid system and its therapeutic exploitation , 2004, Nature Reviews Drug Discovery.

[45]  Jerry L. Hopkins,et al.  Characterization of the allosteric inhibition of a protein-protein interaction by mass spectrometry , 2003, Journal of the American Society for Mass Spectrometry.

[46]  G. Prestwich,et al.  Using photolabile ligands in drug discovery and development. , 2000, Trends in biotechnology.

[47]  E. Sigel,et al.  The benzodiazepine binding site of GABAA receptors. , 1997, Trends in pharmacological sciences.

[48]  E. Sigel,et al.  ReviewThe benzodiazepine binding site of GABAA receptors , 1997 .

[49]  R. Pertwee.  Pharmacology of cannabinoid CB1 and CB2 receptors. , 1997, Pharmacology & therapeutics.

[50]  S. Fleming.  Chemical reagents in photoaffinity labeling , 1995 .

[51]  G. Prestwich,et al.  Benzophenone photophores in biochemistry. , 1994, Biochemistry.

[52]  A. Makriyannis,et al.  5'-Azido-delta 8-THC: a novel photoaffinity label for the cannabinoid receptor. , 1992, Journal of medicinal chemistry.

[53]  H. Okayama,et al.  High-efficiency transformation of mammalian cells by plasmid DNA. , 1987, Molecular and cellular biology.

[54]  D. Martin,et al.  Direct photoaffinity labeling of an allosteric site on subunit protein M1 of mouse ribonucleotide reductase by dTTP. , 1982, Proceedings of the National Academy of Sciences of the United States of America.