Crystal Structure of the Human Cannabinoid Receptor CB1

[1]  Shan Jiang,et al.  Crystal structures of agonist-bound human cannabinoid receptor CB1 , 2017, Nature.

[2]  N. Colabufo,et al.  Editorial: The CB2 Cannabinoid System: A New Strategy in Neurodegenerative Disorder and Neuroinflammation , 2017, Frontiers in Neuroscience.

[3]  Jie Yin,et al.  High-resolution crystal structure of the human CB1 cannabinoid receptor , 2016, Nature.

[4]  Z. Xi,et al.  Cannabinoid Type 2 Receptors Mediate a Cell Type-Specific Plasticity in the Hippocampus , 2016, Neuron.

[5]  Lu Zhang,et al.  In vitro expression and analysis of the 826 human G protein-coupled receptors , 2016, Protein & Cell.

[6]  Arthur Christopoulos,et al.  Crystal structures of the M1 and M4 muscarinic acetylcholine receptors , 2016, Nature.

[7]  A. Makriyannis,et al.  Blockade of Nicotine and Cannabinoid Reinforcement and Relapse by a Cannabinoid CB1-Receptor Neutral Antagonist AM4113 and Inverse Agonist Rimonabant in Squirrel Monkeys , 2016, Neuropsychopharmacology.

[8]  Bas Vroling,et al.  GPCRdb: an information system for G protein-coupled receptors , 2015, Nucleic Acids Res..

[9]  D. Cota,et al.  The Endocannabinoid System: Pivotal Orchestrator of Obesity and Metabolic Disease , 2015, Trends in Endocrinology & Metabolism.

[10]  Berk Hess,et al.  GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers , 2015 .

[11]  K. Mackie,et al.  Molecular-interaction and signaling profiles of AM3677, a novel covalent agonist selective for the cannabinoid 1 receptor. , 2015, ACS chemical neuroscience.

[12]  Xin Xie,et al.  Development of Quinoline-2,4(1H,3H)-diones as Potent and Selective Ligands of the Cannabinoid Type 2 Receptor. , 2015, Journal of medicinal chemistry.

[13]  Penny F Whiting,et al.  Cannabinoids for Medical Use: A Systematic Review and Meta-analysis. , 2015, JAMA.

[14]  Yasuyuki Kihara,et al.  Crystal Structure of Antagonist Bound Human Lysophosphatidic Acid Receptor 1 , 2015, Cell.

[15]  M. Tius,et al.  3'-functionalized adamantyl cannabinoid receptor probes. , 2015, Journal of medicinal chemistry.

[16]  T. Rubino,et al.  Endocannabinoids and Mental Disorders. , 2015, Handbook of experimental pharmacology.

[17]  G. Pryce,et al.  Endocannabinoids in Multiple Sclerosis and Amyotrophic Lateral Sclerosis. , 2015, Handbook of experimental pharmacology.

[18]  L. Bohn,et al.  Approaches to Assess Functional Selectivity in GPCRs: Evaluating G Protein Signaling in an Endogenous Environment. , 2015, Methods in molecular biology.

[19]  J. Ramos,et al.  Endocannabinoids and Neurodegenerative Disorders: Parkinson's Disease, Huntington's Chorea, Alzheimer's Disease, and Others. , 2015, Handbook of experimental pharmacology.

[20]  Brandie M. Ehrmann,et al.  CB2-Selective Cannabinoid Receptor Ligands: Synthesis, Pharmacological Evaluation, and Molecular Modeling Investigation of 1,8-Naphthyridin-2(1H)-one-3-carboxamides , 2014, Journal of medicinal chemistry.

[21]  A. Makriyannis.  2012 Division of medicinal chemistry award address. Trekking the cannabinoid road: a personal perspective. , 2014, Journal of medicinal chemistry.

[22]  Xavier Robert,et al.  Deciphering key features in protein structures with the new ENDscript server , 2014, Nucleic Acids Res..

[23]  J. Wess,et al.  Activation and allosteric modulation of a muscarinic acetylcholine receptor , 2013, Nature.

[24]  D. Farrens,et al.  The membrane proximal region of the cannabinoid receptor CB1 N-terminus can allosterically modulate ligand affinity. , 2013, Biochemistry.

[25]  A. Mallat,et al.  Cannabinoid signaling and liver therapeutics. , 2013, Journal of hepatology.

[26]  V. Auwärter,et al.  Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings. , 2013, Addiction.

[27]  K. Katoh,et al.  MAFFT Multiple Sequence Alignment Software Version 7: Improvements in Performance and Usability , 2013, Molecular biology and evolution.

[28]  Alexander D. MacKerell,et al.  Extension of the CHARMM general force field to sulfonyl‐containing compounds and its utility in biomolecular simulations , 2012, J. Comput. Chem..

[29]  J. Shiloach,et al.  Structure of the agonist-bound neurotensin receptor , 2012, Nature.

[30]  Alexander D. MacKerell,et al.  Optimization of the additive CHARMM all-atom protein force field targeting improved sampling of the backbone φ, ψ and side-chain χ(1) and χ(2) dihedral angles. , 2012, Journal of chemical theory and computation.

[31]  Joshua M. Kunken,et al.  Fusion partner toolchest for the stabilization and crystallization of G protein-coupled receptors. , 2012, Structure.

[32]  Wufeng Tang,et al.  Total synthesis of RNA-polymerase inhibitor ripostatin B and 15-deoxyripostatin A. , 2012, Angewandte Chemie.

[33]  Clemens Vonrhein,et al.  Exploiting structure similarity in refinement: automated NCS and target-structure restraints in BUSTER , 2012, Acta crystallographica. Section D, Biological crystallography.

[34]  Albert C. Pan,et al.  Structure and Dynamics of the M3 Muscarinic Acetylcholine Receptor , 2012, Nature.

[35]  Hugh Rosen,et al.  Crystal Structure of a Lipid G Protein–Coupled Receptor , 2012, Science.

[36]  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.

[37]  A. Makriyannis,et al.  Cannabinoid 1 G protein-coupled receptor (periphero-)neutral antagonists: emerging therapeutics for treating obesity-driven metabolic disease and reducing cardiovascular risk , 2011, Expert opinion on drug discovery.

[38]  VINCENT ZOETE,et al.  SwissParam: A fast force field generation tool for small organic molecules , 2011, J. Comput. Chem..

[39]  I. Weiner,et al.  AVE1625, a cannabinoid CB1 receptor antagonist, as a co-treatment with antipsychotics for schizophrenia: improvement in cognitive function and reduction of antipsychotic-side effects in rodents , 2011, Psychopharmacology.

[40]  D. Kendall,et al.  Ligand binding sensitivity of the extracellular loop two of the cannabinoid receptor 1 , 2010, Drug development research.

[41]  A. Makriyannis,et al.  hCB2 ligand-interaction landscape: cysteine residues critical to biarylpyrazole antagonist binding motif and receptor modulation. , 2010, Chemistry & biology.

[42]  S. Ambudkar,et al.  Peripheral CB1 cannabinoid receptor blockade improves cardiometabolic risk in mouse models of obesity. , 2010, The Journal of clinical investigation.

[43]  A. Savonenko,et al.  Synthesis and biodistribution of [11C]A-836339, a new potential radioligand for PET imaging of cannabinoid type 2 receptors (CB2). , 2010, Bioorganic & medicinal chemistry.

[44]  K. Mackie,et al.  CB2: a cannabinoid receptor with an identity crisis , 2010, British journal of pharmacology.

[45]  P. Emsley,et al.  Features and development of Coot , 2010, Acta crystallographica. Section D, Biological crystallography.

[46]  Randy J. Read,et al.  Acta Crystallographica Section D Biological , 2003 .

[47]  Wolfgang Kabsch,et al.  Integration, scaling, space-group assignment and post-refinement , 2010, Acta crystallographica. Section D, Biological crystallography.

[48]  Alexander D. MacKerell,et al.  CHARMM general force field: A force field for drug‐like molecules compatible with the CHARMM all‐atom additive biological force fields , 2009, J. Comput. Chem..

[49]  R. Stevens,et al.  Rastering strategy for screening and centring of microcrystal samples of human membrane proteins with a sub-10 µm size X-ray synchrotron beam , 2009, Journal of The Royal Society Interface.

[50]  K. Ahn,et al.  Dual Role of the Second Extracellular Loop of the Cannabinoid Receptor 1: Ligand Binding and Receptor Localization , 2009, Molecular Pharmacology.

[51]  Margaret S. Landis,et al.  Discovery of 1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4-ethylaminopiperidine-4-carboxylic acid amide hydrochloride (CP-945,598), a novel, potent, and selective cannabinoid type 1 receptor antagonist. , 2009, Journal of medicinal chemistry.

[52]  Takao Shimizu,et al.  Lipid mediators in health and disease: enzymes and receptors as therapeutic targets for the regulation of immunity and inflammation. , 2009, Annual review of pharmacology and toxicology.

[53]  A. Makriyannis,et al.  Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis. , 2009, Expert opinion on emerging drugs.

[54]  V. Cherezov,et al.  Crystallizing membrane proteins using lipidic mesophases , 2009, Nature Protocols.

[55]  Alexandros Makriyannis,et al.  Ligand-binding architecture of human CB2 cannabinoid receptor: evidence for receptor subtype-specific binding motif and modeling GPCR activation. , 2008, Chemistry & biology.

[56]  R. Stevens,et al.  Microscale fluorescent thermal stability assay for membrane proteins. , 2008, Structure.

[57]  A. Hohmann,et al.  Cannabinoid CB2 receptors: a therapeutic target for the treatment of inflammatory and neuropathic pain , 2008, British journal of pharmacology.

[58]  G. Cabral,et al.  CB2 receptors in the brain: role in central immune function , 2008, British journal of pharmacology.

[59]  C. Lunn,et al.  Biology and therapeutic potential of cannabinoid CB2 receptor inverse agonists , 2008, British journal of pharmacology.

[60]  Hui-lin Li.  An archaeological and historical account of cannabis in China , 1973, Economic Botany.

[61]  Randy J. Read,et al.  Phaser crystallographic software , 2007, Journal of applied crystallography.

[62]  R. Pertwee.  Cannabinoids and Multiple Sclerosis , 2007, Molecular Neurobiology.

[63]  D. Macintyre,et al.  Antiobesity Efficacy of a Novel Cannabinoid-1 Receptor Inverse Agonist, N-[(1S,2S)-3-(4-Chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (MK-0364), in Rodents , 2007, Journal of Pharmacology and Experimental Therapeutics.

[64]  Matthew P. Repasky,et al.  Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. , 2006, Journal of medicinal chemistry.

[65]  K. Ahn,et al.  Mutations of CB1 T210 produce active and inactive receptor forms: correlations with ligand affinity, receptor stability, and cellular localization. , 2006, Biochemistry.

[66]  R. Larson,et al.  Molecular dynamics simulations of model trans-membrane peptides in lipid bilayers: a systematic investigation of hydrophobic mismatch. , 2006, Biophysical journal.

[67]  R. Friesner,et al.  Novel procedure for modeling ligand/receptor induced fit effects. , 2006, Journal of medicinal chemistry.

[68]  A. Makriyannis,et al.  (-)-7′-Isothiocyanato-11-hydroxy-1′,1′-dimethylheptylhexahydrocannabinol (AM841), a High-Affinity Electrophilic Ligand, Interacts Covalently with a Cysteine in Helix Six and Activates the CB1 Cannabinoid Receptor , 2005, Molecular Pharmacology.

[69]  K. Mackie,et al.  Identification functional characterization of brainstem cannabinoid CB2 receptors. , 2022 .

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

[71]  D. Farrens,et al.  Cysteine residues in the human cannabinoid receptor: only C257 and C264 are required for a functional receptor, and steric bulk at C386 impairs antagonist SR141716A binding. , 2005, Biochemistry.

[72]  J. Lange,et al.  Keynote review: Medicinal chemistry strategies to CB1 cannabinoid receptor antagonists. , 2005, Drug discovery today.

[73]  B. Cravatt,et al.  The endogenous cannabinoid system and its role in nociceptive behavior. , 2004, Journal of neurobiology.

[74]  Alexander D. MacKerell,et al.  Extending the treatment of backbone energetics in protein force fields: Limitations of gas‐phase quantum mechanics in reproducing protein conformational distributions in molecular dynamics simulations , 2004, J. Comput. Chem..

[75]  R. Buchert,et al.  [123I]AM281 single-photon emission computed tomography imaging of central cannabinoid CB1 receptors before and after Δ9-tetrahydrocannabinol therapy and whole-body scanning for assessment of radiation dose in tourette patients , 2004, Biological Psychiatry.

[76]  Hege S. Beard,et al.  Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. , 2004, Journal of medicinal chemistry.

[77]  Matthew P. Repasky,et al.  Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. , 2004, Journal of medicinal chemistry.

[78]  Mary E Abood,et al.  An aromatic microdomain at the cannabinoid CB(1) receptor constitutes an agonist/inverse agonist binding region. , 2003, Journal of medicinal chemistry.

[79]  G. von Heijne,et al.  Membrane assembly of the cannabinoid receptor 1: impact of a long N-terminal tail. , 2003, Molecular pharmacology.

[80]  Gert Vriend,et al.  GPCRDB information system for G protein-coupled receptors , 2003, Nucleic Acids Res..

[81]  D. Lynch,et al.  N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A) interaction with LYS 3.28(192) is crucial for its inverse agonism at the cannabinoid CB1 receptor. , 2002, Molecular pharmacology.

[82]  Ming-Jung Wu,et al.  Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding. , 2000, Drug and alcohol dependence.

[83]  Alexander D. MacKerell,et al.  An Improved Empirical Potential Energy Function for Molecular Simulations of Phospholipids , 2000 .

[84]  Patricia H. Reggio,et al.  The Difference between the CB1 and CB2Cannabinoid Receptors at Position 5.46 Is Crucial for the Selectivity of WIN55212-2 for CB2 , 1999 .

[85]  K. Mackie,et al.  Distinct Domains of the CB1 Cannabinoid Receptor Mediate Desensitization and Internalization , 1999, The Journal of Neuroscience.

[86]  A. Makriyannis,et al.  Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. , 1999, Journal of medicinal chemistry.

[87]  D. Hurst,et al.  The difference between the CB(1) and CB(2) cannabinoid receptors at position 5.46 is crucial for the selectivity of WIN55212-2 for CB(2). , 1999, Molecular pharmacology.

[88]  S. Ikeda,et al.  SR 141716A acts as an inverse agonist to increase neuronal voltage-dependent Ca2+ currents by reversal of tonic CB1 cannabinoid receptor activity. , 1998, Molecular pharmacology.

[89]  L. Petrocellis,et al.  An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. , 1998, European journal of pharmacology.

[90]  D. R. Compton,et al.  Structure-activity relationships of indole- and pyrrole-derived cannabinoids. , 1998, The Journal of pharmacology and experimental therapeutics.

[91]  Alexander D. MacKerell,et al.  All-atom empirical potential for molecular modeling and dynamics studies of proteins. , 1998, The journal of physical chemistry. B.

[92]  P. Casellas,et al.  SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor. , 1998, The Journal of pharmacology and experimental therapeutics.

[93]  D. Kendall,et al.  Ligand Binding and Modulation of Cyclic AMP Levels Depend on the Chemical Nature of Residue 192 of the Human Cannabinoid Receptor 1 , 1998, Journal of neurochemistry.

[94]  Payton King,et al.  Imaging the Brain Marijuana Receptor: Development of a Radioligand that Binds to Cannabinoid CB1 Receptors In Vivo , 1998, Journal of neurochemistry.

[95]  D. R. Compton,et al.  Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. , 1996, The Journal of pharmacology and experimental therapeutics.

[96]  T. Bonner,et al.  A lysine residue of the cannabinoid receptor is critical for receptor recognition by several agonists but not WIN55212-2. , 1996, Molecular pharmacology.

[97]  Anneliese Schrott-Fischer,et al.  Quantitative evaluation of myelinated nerve fibres and hair cells in cochleae of humans with age-related high-tone hearing loss , 1995, Hearing Research.

[98]  K. Mackie,et al.  Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. , 1995, Molecular pharmacology.

[99]  T. Mavromoustakos,et al.  Small angle X-ray diffraction and differential scanning calorimetric studies on O-methyl-(-)-delta 8-tetrahydrocannabinol and its 5' iodinated derivative in membrane bilayers. , 1995, Biochimica et biophysica acta.

[100]  Z. Vogel,et al.  Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. , 1995, Biochemical pharmacology.

[101]  J. Ballesteros,et al.  Construction of a 3D model of the cannabinoid CB1 receptor: determination of helix ends and helix orientation. , 1995, Life sciences.

[102]  J. Ballesteros,et al.  [19] Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G protein-coupled receptors , 1995 .

[103]  A. Makriyannis,et al.  (-)-11-Hydroxy-7'-isothiocyanato-1',1'-dimethylheptyl-delta 8-THC: a novel, high-affinity irreversible probe for the cannabinoid receptor in the brain. , 1994, Journal of medicinal chemistry.

[104]  Collaborative Computational,et al.  The CCP4 suite: programs for protein crystallography. , 1994, Acta crystallographica. Section D, Biological crystallography.

[105]  P. Soubrié,et al.  SR141716A, a potent and selective antagonist of the brain cannabinoid receptor , 1994, FEBS letters.

[106]  R. Abagyan,et al.  Biased probability Monte Carlo conformational searches and electrostatic calculations for peptides and proteins. , 1994, Journal of molecular biology.

[107]  S. Munro,et al.  Molecular characterization of a peripheral receptor for cannabinoids , 1993, Nature.

[108]  D. Haycock,et al.  Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids. , 1993, The Journal of pharmacology and experimental therapeutics.

[109]  D. Gibson,et al.  Isolation and structure of a brain constituent that binds to the cannabinoid receptor. , 1992, Science.

[110]  T. Bonner,et al.  Structure of a cannabinoid receptor and functional expression of the cloned cDNA , 1990, Nature.

[111]  M. Herkenham,et al.  Cannabinoid receptor localization in brain. , 1990, Proceedings of the National Academy of Sciences of the United States of America.

[112]  R. Rapaka,et al.  The molecular basis of cannabinoid activity. , 1990, Life sciences.

[113]  A. Howlett,et al.  Determination and characterization of a cannabinoid receptor in rat brain. , 1988, Molecular pharmacology.

[114]  R. Razdan,et al.  Structure-activity relationships of the cannabinoids. , 1986, NIDA research monograph.

[115]  R. Yeates,et al.  The reaction between organic nitrates and sulfhydryl compounds. A possible model system for the activation of organic nitrates. , 1985, Molecular pharmacology.

[116]  A. Howlett.  Cannabinoid inhibition of adenylate cyclase. Biochemistry of the response in neuroblastoma cell membranes. , 1985, Molecular pharmacology.

[117]  L. Lemberger.  Potential therapeutic usefulness of marijuana. , 1980, Annual review of pharmacology and toxicology.

[118]  R. Mechoulam,et al.  Isolation, Structure, and Partial Synthesis of an Active Constituent of Hashish , 1964 .

[119]  G. Brown,et al.  ORGANIC NITRATES AS SYNTHETIC INTERMEDIATES: PREPARATIONS OF NITRATES AND SOME REPRESENTATIVE REACTIONS , 1956 .

[120]  S. Loewe,et al.  Tetrahydrocannabinol homologs with double branched alkyl groups in the 3-position. , 1948, Journal of the American Chemical Society.

[121]  J. R. Matchett,et al.  Isolation of a Physiologically Active Tetrahydrocannabinol from Cannabis Sativa Resin , 1942 .

[122]  S. Wilkinson,et al.  206. Cannabis indica. Part IV. The synthesis of some tetrahydrodibenzopyran derivatives , 1940 .