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Volumn 49, Issue 3, 2006, Pages 984-994

Cannabinoid CB2/CB1 selectivity. Receptor modeling and automated docking analysis

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; DOCKING PROTEIN; RECEPTOR SUBTYPE; RHODOPSIN;

EID: 32344446060     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050875u     Document Type: Article
Times cited : (94)

References (58)
  • 1
    • 33947489961 scopus 로고
    • Isolation, structure, and partial synthesis of an active constituent of hashish
    • Gaoni, Y.; Mechoulam R. Isolation, structure, and partial synthesis of an active constituent of hashish. J. Am. Chem. Soc. 1964, 86, 1646-16477.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 1646-16477
    • Gaoni, Y.1    Mechoulam, R.2
  • 2
    • 0033118863 scopus 로고    scopus 로고
    • From gan-zi-gun-nu to anandamide and 2-arachidonoylglycerol: The ongoing story of cannabis
    • Mechoulam, R.; Ben-Shabat, S. From gan-zi-gun-nu to anandamide and 2-arachidonoylglycerol: the ongoing story of cannabis. Nat. Prod. Rev. 1999, 16, 131-143.
    • (1999) Nat. Prod. Rev. , vol.16 , pp. 131-143
    • Mechoulam, R.1    Ben-Shabat, S.2
  • 4
    • 0025325535 scopus 로고
    • Structure of a cannabinoid receptor and functional expression of the cloned cDNA
    • Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 1990, 346, 561-564.
    • (1990) Nature , vol.346 , pp. 561-564
    • Matsuda, L.A.1    Lolait, S.J.2    Brownstein, M.J.3    Young, A.C.4    Bonner, T.I.5
  • 5
    • 0029979034 scopus 로고    scopus 로고
    • Recent developments in the medicinal chemistry of cannabinoids
    • Huffman, J. W.; Lainton, J. A. H. Recent developments in the medicinal chemistry of cannabinoids. Curr. Med. Chem. 1996, 3, 101-116.
    • (1996) Curr. Med. Chem. , vol.3 , pp. 101-116
    • Huffman, J.W.1    Lainton, J.A.H.2
  • 7
    • 0032802188 scopus 로고    scopus 로고
    • Pharmacology of cannabinoid receptor ligands
    • Pertwee, R. G. Pharmacology of cannabinoid receptor ligands. Curr. Med. Chem. 1999, 6, 635-664.
    • (1999) Curr. Med. Chem. , vol.6 , pp. 635-664
    • Pertwee, R.G.1
  • 11
    • 0042991377 scopus 로고    scopus 로고
    • Pharmacophores for ligand recognition and activation/ inactivation of the cannabinoid receptors
    • Reggio, P. H. Pharmacophores for ligand recognition and activation/ inactivation of the cannabinoid receptors. Curr. Pharm. Des. 2003, 9, 1607-1633.
    • (2003) Curr. Pharm. Des. , vol.9 , pp. 1607-1633
    • Reggio, P.H.1
  • 12
    • 0032199006 scopus 로고    scopus 로고
    • Binding, gating, affinity and efficacy: The interpretation of structure-activity relationships for agonists and of the effects of mutating receptors
    • Colquhoun D. Binding, gating, affinity and efficacy: the interpretation of structure-activity relationships for agonists and of the effects of mutating receptors. Br. J. Pharmacol. 1998, 125, 924-947.
    • (1998) Br. J. Pharmacol. , vol.125 , pp. 924-947
    • Colquhoun, D.1
  • 13
    • 0034464742 scopus 로고    scopus 로고
    • Uncovering molecular mechanisms involved in activation of G protein-coupled receptors
    • Gether U. Uncovering molecular mechanisms involved in activation of G protein-coupled receptors. Endocr. Rev. 2000, 21, 90-113.
    • (2000) Endocr. Rev. , vol.21 , pp. 90-113
    • Gether, U.1
  • 15
    • 0032795627 scopus 로고    scopus 로고
    • Ligand-ligand and ligand-receptor approaches to modeling the cannabinoid CB1 and CB2 receptors: Achievements and challenges
    • Reggio, P. H. Ligand-ligand and ligand-receptor approaches to modeling the cannabinoid CB1 and CB2 receptors: achievements and challenges. Curr. Med. Chem. 1999, 6, 665-683.
    • (1999) Curr. Med. Chem. , vol.6 , pp. 665-683
    • Reggio, P.H.1
  • 16
    • 0029866824 scopus 로고    scopus 로고
    • A lysine residue of the cannabinoid receptor is critical for receptor recognition by several agonists but not WIN55212-2
    • Song, Z. H.; Bonner, T. I. A lysine residue of the cannabinoid receptor is critical for receptor recognition by several agonists but not WIN55212-2. Mol. Pharmacol. 1996, 49, 891-896.
    • (1996) Mol. Pharmacol. , vol.49 , pp. 891-896
    • Song, Z.H.1    Bonner, T.I.2
  • 18
    • 0032860406 scopus 로고    scopus 로고
    • The difference between the CB1 and CB2 cannabinoid receptors at position 5.46 is crucial for the selectivity of WIN55212-2 for CB2
    • Song, Z. H.; Slowey, C. A.; Hurst, D. P.; Reggio, P. H. The difference between the CB1 and CB2 cannabinoid receptors at position 5.46 is crucial for the selectivity of WIN55212-2 for CB2. Mol. Pharmacol. 1999, 56, 834-840.
    • (1999) Mol. Pharmacol. , vol.56 , pp. 834-840
    • Song, Z.H.1    Slowey, C.A.2    Hurst, D.P.3    Reggio, P.H.4
  • 19
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a lamarckian genetic algorithm and empirical binding free energy function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a lamarckian genetic algorithm and empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 20
    • 0027968068 scopus 로고
    • CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice
    • Thompson, J. D.; Higgins, D. G.; Gibson, T. J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 1994, 22, 4673-4680.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 4673-4680
    • Thompson, J.D.1    Higgins, D.G.2    Gibson, T.J.3
  • 21
    • 0034044314 scopus 로고    scopus 로고
    • The PSIPRED protein structure prediction server
    • McGuffin, L. J.; Bryson, K.; Jones, D. T. The PSIPRED protein structure prediction server. Bioinformatics 2000, 16, 404-405.
    • (2000) Bioinformatics , vol.16 , pp. 404-405
    • McGuffin, L.J.1    Bryson, K.2    Jones, D.T.3
  • 22
    • 0033578684 scopus 로고    scopus 로고
    • Protein secondary structure prediction based on position-specific scoring matrices
    • Jones, D. T.; Protein secondary structure prediction based on position-specific scoring matrices. J. Mol. Biol. 1999, 292, 195-202.
    • (1999) J. Mol. Biol. , vol.292 , pp. 195-202
    • Jones, D.T.1
  • 24
    • 0035800850 scopus 로고    scopus 로고
    • Activation of the beta 2-adrenergic receptor involves disruption of an ionic lock between the cytoplasmic ends of transmembrane segments 3 and 6
    • Ballesteros, J. A.; Jensen, A. D.; Liapakis, G.; Rasmussen, S. G.; Shi, L.; Gether, U.; Javitch, J. A. Activation of the beta 2-adrenergic receptor involves disruption of an ionic lock between the cytoplasmic ends of transmembrane segments 3 and 6. J. Biol. Chem. 2001, 276, 29171-29177.
    • (2001) J. Biol. Chem. , vol.276 , pp. 29171-29177
    • Ballesteros, J.A.1    Jensen, A.D.2    Liapakis, G.3    Rasmussen, S.G.4    Shi, L.5    Gether, U.6    Javitch, J.A.7
  • 25
    • 0034327611 scopus 로고    scopus 로고
    • Hinges, swivels and switches: The role of pralines in signalling via transmembrane alpha-helices
    • Sansom, M. S.; Weinstein, H. Hinges, swivels and switches: the role of pralines in signalling via transmembrane alpha-helices. Trends Pharmacol. Sci. 2000, 21, 445-451.
    • (2000) Trends Pharmacol. Sci. , vol.21 , pp. 445-451
    • Sansom, M.S.1    Weinstein, H.2
  • 26
    • 0035937786 scopus 로고    scopus 로고
    • Agonist-induced conformational changes at the cytoplasmic side of transmembrane segment 6 in the beta 2 adrenergic receptor mapped by site-selective fluorescent labeling
    • Jensen, A. D.; Guarnieri, F.; Rasmussen, S. G.; Asmar, F.; Ballesteros, J. A.; Gether U. Agonist-induced conformational changes at the cytoplasmic side of transmembrane segment 6 in the beta 2 adrenergic receptor mapped by site-selective fluorescent labeling. J. Biol. Chem. 2001, 276, 9279-9290.
    • (2001) J. Biol. Chem. , vol.276 , pp. 9279-9290
    • Jensen, A.D.1    Guarnieri, F.2    Rasmussen, S.G.3    Asmar, F.4    Ballesteros, J.A.5    Gether, U.6
  • 27
    • 0037174606 scopus 로고    scopus 로고
    • Beta2 adrenergic receptor activation. Modulation of the proline kink in transmembrane 6 by a rotamer toggle switch
    • Shi, L.; Liapakis, G.; Xu, R.; Guarnieri, F.; Ballesteros, J. A.; Javitch, J. A. Beta2 adrenergic receptor activation. Modulation of the proline kink in transmembrane 6 by a rotamer toggle switch. J. Biol. Chem. 2002, 277, 40989-40996.
    • (2002) J. Biol. Chem. , vol.277 , pp. 40989-40996
    • Shi, L.1    Liapakis, G.2    Xu, R.3    Guarnieri, F.4    Ballesteros, J.A.5    Javitch, J.A.6
  • 28
    • 0036954833 scopus 로고    scopus 로고
    • Activation of the cannabinoid CB1 receptor may involve a W6.48/F3.36 rotamer toggle switch
    • Singh, R.; Hurst, D. P.; Barnett-Norris, J.; Lynch, D. L.; Reggio, P. H.; Guarnieri F. Activation of the cannabinoid CB1 receptor may involve a W6.48/F3.36 rotamer toggle switch. J. Pept. Res. 2002, 60, 357-370.
    • (2002) J. Pept. Res. , vol.60 , pp. 357-370
    • Singh, R.1    Hurst, D.P.2    Barnett-Norris, J.3    Lynch, D.L.4    Reggio, P.H.5    Guarnieri, F.6
  • 29
    • 0000243829 scopus 로고
    • PROCHECK: A program to check the stereochemical quality of protein structures
    • Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thorton, J. M. PROCHECK: a program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 1993, 26, 283-291.
    • (1993) J. Appl. Crystallogr. , vol.26 , pp. 283-291
    • Laskowski, R.A.1    MacArthur, M.W.2    Moss, D.S.3    Thorton, J.M.4
  • 31
    • 32344451519 scopus 로고    scopus 로고
    • Molecular Disovery Ltd.
    • GRID v. 22 Molecular Disovery Ltd. (http://www.moldiscovery.com).
    • GRID V. 22
  • 34
    • 32344441500 scopus 로고    scopus 로고
    • note
    • Unpublished results from our laboratory.
  • 35
    • 1642543378 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 1,8-naphthyridin-4(1H)-on-3- carboxamide derivatives as new ligands of cannabinoid receptors
    • Ferrarini, P. L.; Calderone, V.; Cavallini, T.; Manera, C.; Saccomanni, G.; Pani, L.; Ruiu, S.; Gessa, G. L. Synthesis and biological evaluation of 1,8-naphthyridin-4(1H)-on-3-carboxamide derivatives as new ligands of cannabinoid receptors. Bioorg. Med. Chem. 2004, 12, 1921-1933.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 1921-1933
    • Ferrarini, P.L.1    Calderone, V.2    Cavallini, T.3    Manera, C.4    Saccomanni, G.5    Pani, L.6    Ruiu, S.7    Gessa, G.L.8
  • 39
    • 11844249400 scopus 로고    scopus 로고
    • Homology models of the cannabinoid CB1 and CB2 receptors. A docking analysis study
    • Montero, C.; Campillo, N. E.; Goya, P.; Páez, J. A. Homology models of the cannabinoid CB1 and CB2 receptors. A docking analysis study. Eur. J. Med. Chem. 2005, 40, 75-83.
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 75-83
    • Montero, C.1    Campillo, N.E.2    Goya, P.3    Páez, J.A.4
  • 40
    • 0038119607 scopus 로고    scopus 로고
    • Homology model of the CB1 cannabinoid receptor: Sites critical for nonclassical cannabinoid agonist interaction
    • Shim, J. Y.; Welsh, W. J.; Howlett, A. C. Homology model of the CB1 cannabinoid receptor: sites critical for nonclassical cannabinoid agonist interaction. Biopolymers 2003, 71, 169-189.
    • (2003) Biopolymers , vol.71 , pp. 169-189
    • Shim, J.Y.1    Welsh, W.J.2    Howlett, A.C.3
  • 41
    • 0141704146 scopus 로고    scopus 로고
    • 3D structural model of the G-protein-coupled cannabinoid CB2 receptor
    • Xie, X. Q.; Chen, J. Z.; Billings, E. M. 3D structural model of the G-protein-coupled cannabinoid CB2 receptor. Proteins 2003, 53, 307-319.
    • (2003) Proteins , vol.53 , pp. 307-319
    • Xie, X.Q.1    Chen, J.Z.2    Billings, E.M.3
  • 43
    • 77957055780 scopus 로고
    • Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G-protein coupled receptors
    • Ballesteros, J. A.; Weinstein, H. W. Integrated methods for the construction of three-dimensional models and computational probing of structure-function relations in G-protein coupled receptors. Methods Neurosci. 1995, 25, 366-428.
    • (1995) Methods Neurosci. , vol.25 , pp. 366-428
    • Ballesteros, J.A.1    Weinstein, H.W.2
  • 47
    • 0029078977 scopus 로고
    • Construction of a 3D model of the cannabinoid CB1 receptor: Determination of helix ends and helix orientation
    • Bramblett, R. D.; Panu, A. M.; Ballesteros, J. A.; Reggio, P. H. Construction of a 3D model of the cannabinoid CB1 receptor: determination of helix ends and helix orientation. Life Sci. 1995, 56, 1971-1982.
    • (1995) Life Sci. , vol.56 , pp. 1971-1982
    • Bramblett, R.D.1    Panu, A.M.2    Ballesteros, J.A.3    Reggio, P.H.4
  • 50
    • 0037716778 scopus 로고    scopus 로고
    • Integrity of extracellular loop 1 of the human cannabinoid receptor 1 is critical for high-affinity binding of the ligand CP55940 but not SR 141716A
    • Murphy, J. W.; Kendall, D. A. Integrity of extracellular loop 1 of the human cannabinoid receptor 1 is critical for high-affinity binding of the ligand CP55940 but not SR 141716A. Biochem. Pharmacol. 2003, 65, 1623-1631.
    • (2003) Biochem. Pharmacol. , vol.65 , pp. 1623-1631
    • Murphy, J.W.1    Kendall, D.A.2
  • 52
    • 32344440449 scopus 로고    scopus 로고
    • Schrodinger Inc.
    • Macromodel ver. 8.5, Schrodinger Inc., 1999.
    • (1999) Macromodel Ver. 8.5
  • 53
    • 32344447679 scopus 로고    scopus 로고
    • Accelrys Inc., San Diego, CA
    • WebLab Viewer Pro 3.7 (Accelrys Inc., San Diego, CA).
    • WebLab Viewer Pro 3.7
  • 56
    • 0033166313 scopus 로고    scopus 로고
    • Effect of adjoining aromatic ring upon excited-state proton transfer, o-hydroxybenzaldehyde
    • Cuma, M.; Scheiner, S.; Kar, T. Effect of adjoining aromatic ring upon excited-state proton transfer, o-hydroxybenzaldehyde. THEOCHEM 1999, 467, 37-49.
    • (1999) THEOCHEM , vol.467 , pp. 37-49
    • Cuma, M.1    Scheiner, S.2    Kar, T.3
  • 57
    • 58149324166 scopus 로고
    • A comparison of the accuracy of different functionals
    • Bauschlicher, C. W. A comparison of the accuracy of different functionals. Chem. Phys. Lett. 1995, 246, 40-44.
    • (1995) Chem. Phys. Lett. , vol.246 , pp. 40-44
    • Bauschlicher, C.W.1
  • 58
    • 32344438433 scopus 로고    scopus 로고
    • http://www.scripps.edu/∼sanner/python/adt


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