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Volumn 88, Issue 2, 2015, Pages 238-244

Structural basis of species-dependent differential affinity of 6-alkoxy-5-aryl-3-pyridinecarboxamide cannabinoid-1 receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

5-(4-CHLOROPHENYL)-6-(CYCLOPROPYLMETHOXY)-N-(2-HYDROXYCYCLOHEXYL)-3-PYRIDINECARBOXAMIDE; 5-(4-CHLOROPHENYL)-N-(2-HYDROXYCYCLOHEXYL)-6-(2-METHOXYETHOXY)-3-PYRIDINECARBOXAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID RECEPTOR ANTAGONIST; CNR1 PROTEIN, HUMAN; CNR1 PROTEIN, MOUSE; ISOLEUCINE; NICOTINAMIDE; PIPERIDINE DERIVATIVE; PYRAZOLE DERIVATIVE; RIMONABANT;

EID: 84939795965     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.115.098541     Document Type: Article
Times cited : (14)

References (36)
  • 1
    • 0031028923 scopus 로고    scopus 로고
    • Isolation and expression of a mouse CB1 cannabinoid receptor gene. Comparison of binding properties with those of native CB1 receptors in mouse brain and N18TG2 neuroblastoma cells
    • Abood ME, Ditto KE, Noel MA, Showalter VM, and Tao Q (1997) Isolation and expression of a mouse CB1 cannabinoid receptor gene. Comparison of binding properties with those of native CB1 receptors in mouse brain and N18TG2 neuroblastoma cells. Biochem Pharmacol 53:207-214.
    • (1997) Biochem Pharmacol , vol.53 , pp. 207-214
    • Abood, M.E.1    Ditto, K.E.2    Noel, M.A.3    Showalter, V.M.4    Tao, Q.5
  • 3
    • 2442710044 scopus 로고    scopus 로고
    • Genetic vulnerability to diet-induced obesity in the C57BL/6J mouse: Physiological and molecular characteristics
    • Collins S, Martin TL, Surwit RS, and Robidoux J (2004) Genetic vulnerability to diet-induced obesity in the C57BL/6J mouse: physiological and molecular characteristics. Physiol Behav 81:243-248.
    • (2004) Physiol Behav , vol.81 , pp. 243-248
    • Collins, S.1    Martin, T.L.2    Surwit, R.S.3    Robidoux, J.4
  • 6
    • 27844463517 scopus 로고    scopus 로고
    • Effects of rimonabant on metabolic risk factors in overweight patients with dyslipidemia
    • Després JP, Golay A, and Sjöström L; Rimonabant in Obesity-Lipids Study Group (2005) Effects of rimonabant on metabolic risk factors in overweight patients with dyslipidemia. N Engl J Med 353:2121-2134.
    • (2005) N Engl J Med , vol.353 , pp. 2121-2134
    • Després, J.P.1    Golay, A.2    Sjöström, L.3
  • 8
    • 0031863268 scopus 로고    scopus 로고
    • Evaluation of cannabinoid receptor agonists and antagonists using the guanosine-5′-O-(3-[35S] thio)-triphosphate binding assay in rat cerebellar membranes
    • Griffin G, Atkinson PJ, Showalter VM, Martin BR, and Abood ME (1998) Evaluation of cannabinoid receptor agonists and antagonists using the guanosine-5′-O-(3-[35S] thio)-triphosphate binding assay in rat cerebellar membranes. J Pharmacol Exp Ther 285:553-560.
    • (1998) J Pharmacol Exp Ther , vol.285 , pp. 553-560
    • Griffin, G.1    Atkinson, P.J.2    Showalter, V.M.3    Martin, B.R.4    Abood, M.E.5
  • 9
    • 5644244290 scopus 로고    scopus 로고
    • Comparison of cannabinoid ligands affinities and efficacies in murine tissues and in transfected cells expressing human recombinant cannabinoid receptors
    • Govaerts SJ, Hermans E, and Lambert DM (2004) Comparison of cannabinoid ligands affinities and efficacies in murine tissues and in transfected cells expressing human recombinant cannabinoid receptors. Eur J Pharm Sci 23: 233-243.
    • (2004) Eur J Pharm Sci , vol.23 , pp. 233-243
    • Govaerts, S.J.1    Hermans, E.2    Lambert, D.M.3
  • 11
    • 0036892304 scopus 로고    scopus 로고
    • 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
    • Hurst DP, Lynch DL, Barnett-Norris J, Hyatt SM, Seltzman HH, Zhong M, Song ZH, Nie J, Lewis D, and Reggio PH (2002) 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. Mol Pharmacol 62:1274-1287.
    • (2002) Mol Pharmacol , vol.62 , pp. 1274-1287
    • Hurst, D.P.1    Lynch, D.L.2    Barnett-Norris, J.3    Hyatt, S.M.4    Seltzman, H.H.5    Zhong, M.6    Song, Z.H.7    Nie, J.8    Lewis, D.9    Reggio, P.H.10
  • 13
    • 84883784100 scopus 로고    scopus 로고
    • Activation of the Nlrp3 inflammasome in infiltrating macrophages by endocannabinoids mediates beta cell loss in type 2 diabetes
    • Jourdan T, Godlewski G, Cinar R, Bertola A, Szanda G, Liu J, Tam J, Han T, Mukhopadhyay B, and Skarulis MC et al. (2013) Activation of the Nlrp3 inflammasome in infiltrating macrophages by endocannabinoids mediates beta cell loss in type 2 diabetes. Nat Med 19:1132-1140.
    • (2013) Nat Med , vol.19 , pp. 1132-1140
    • Jourdan, T.1    Godlewski, G.2    Cinar, R.3    Bertola, A.4    Szanda, G.5    Liu, J.6    Tam, J.7    Han, T.8    Mukhopadhyay, B.9    Skarulis, M.C.10
  • 14
    • 34347352212 scopus 로고    scopus 로고
    • Mutation studies of Ser7.39 and Ser2.60 in the human CB1 cannabinoid receptor: Evidence for a serine-induced bend in CB1 transmembrane helix 7
    • Kapur A, Hurst DP, Fleischer D, Whitnell R, Thakur GA, Makriyannis A, Reggio PH, and Abood ME (2007) Mutation studies of Ser7.39 and Ser2.60 in the human CB1 cannabinoid receptor: evidence for a serine-induced bend in CB1 transmembrane helix 7. Mol Pharmacol 71:1512-1524.
    • (2007) Mol Pharmacol , vol.71 , pp. 1512-1524
    • Kapur, A.1    Hurst, D.P.2    Fleischer, D.3    Whitnell, R.4    Thakur, G.A.5    Makriyannis, A.6    Reggio, P.H.7    Abood, M.E.8
  • 16
    • 0026244229 scopus 로고
    • MOLSCRIPT: A program to produce both detailed and schematic plots of protein structures
    • Kraulis PJ (1991) MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures. J Appl Cryst 24:946-950.
    • (1991) J Appl Cryst , vol.24 , pp. 946-950
    • Kraulis, P.J.1
  • 17
    • 43449091899 scopus 로고    scopus 로고
    • Effects of rimonabant, a cannabinoid CB1 receptor ligand, on energy expenditure in lean rats
    • Kunz I, Meier MK, Bourson A, Fisseha M, and Schilling W (2008) Effects of rimonabant, a cannabinoid CB1 receptor ligand, on energy expenditure in lean rats. Int J Obes (Lond) 32:863-870.
    • (2008) Int J Obes (Lond) , vol.32 , pp. 863-870
    • Kunz, I.1    Meier, M.K.2    Bourson, A.3    Fisseha, M.4    Schilling, W.5
  • 18
    • 67649418026 scopus 로고    scopus 로고
    • The future of endocannabinoid-oriented clinical research after CB1 antagonists
    • Le Foll B, Gorelick DA, and Goldberg SR (2009) The future of endocannabinoid-oriented clinical research after CB1 antagonists. Psychopharmacology (Berl) 205: 171-174.
    • (2009) Psychopharmacology (Berl) , vol.205 , pp. 171-174
    • Le Foll, B.1    Gorelick, D.A.2    Goldberg, S.R.3
  • 19
    • 41849121146 scopus 로고    scopus 로고
    • Conformational analysis and receptor docking of N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide (taranabant, MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist
    • Lin LS, Ha S, Ball RG, Tsou NN, Castonguay LA, Doss GA, Fong TM, Shen CP, Xiao JC, and Goulet MT et al. (2008) Conformational analysis and receptor docking of N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide (taranabant, MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist. J Med Chem 51:2108-2114.
    • (2008) J Med Chem , vol.51 , pp. 2108-2114
    • Lin, L.S.1    Ha, S.2    Ball, R.G.3    Tsou, N.N.4    Castonguay, L.A.5    Doss, G.A.6    Fong, T.M.7    Shen, C.P.8    Xiao, J.C.9    Goulet, M.T.10
  • 20
    • 13244249625 scopus 로고    scopus 로고
    • Effects of the cannabinoid CB1 receptor antagonist SR141716 on oxygen consumption and soleus muscle glucose uptake in Lep(ob)/Lep(ob) mice
    • Liu YL, Connoley IP, Wilson CA, and Stock MJ (2005) Effects of the cannabinoid CB1 receptor antagonist SR141716 on oxygen consumption and soleus muscle glucose uptake in Lep(ob)/Lep(ob) mice. Int J Obes (Lond) 29:183-187.
    • (2005) Int J Obes (Lond) , vol.29 , pp. 183-187
    • Liu, Y.L.1    Connoley, I.P.2    Wilson, C.A.3    Stock, M.J.4
  • 22
    • 0030815133 scopus 로고    scopus 로고
    • Raster3D: Photorealistic molecular graphics
    • Merritt EA and Bacon DJ (1997) Raster3D: photorealistic molecular graphics. Methods Enzymol 277:505-524.
    • (1997) Methods Enzymol , vol.277 , pp. 505-524
    • Merritt, E.A.1    Bacon, D.J.2
  • 24
    • 33748703859 scopus 로고    scopus 로고
    • The endocannabinoid system as an emerging target of pharmacotherapy
    • Pacher P, Bátkai S, and Kunos G (2006) The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol Rev 58:389-462.
    • (2006) Pharmacol Rev , vol.58 , pp. 389-462
    • Pacher, P.1    Bátkai, S.2    Kunos, G.3
  • 25
    • 84879005796 scopus 로고    scopus 로고
    • Rimonabant dimorphism and its pressure-temperature phase diagram: A delicate case of overall monotropic behavior
    • Perrin MA, Bauer M, Barrio M, Tamarit JL, Céolin R, and Rietveld IB (2013) Rimonabant dimorphism and its pressure-temperature phase diagram: a delicate case of overall monotropic behavior. J Pharm Sci 102:2311-2321.
    • (2013) J Pharm Sci , vol.102 , pp. 2311-2321
    • Perrin, M.A.1    Bauer, M.2    Barrio, M.3    Tamarit, J.L.4    Céolin, R.5    Rietveld, I.B.6
  • 26
    • 32644441249 scopus 로고    scopus 로고
    • Effect of rimonabant, a cannabinoid-1 receptor blocker, on weight and cardiometabolic risk factors in overweight or obese patients: RIO-North America: A randomized controlled trial
    • Pi-Sunyer FX, Aronne LJ, Heshmati HM, Devin J, and Rosenstock J; RIO-North America Study Group (2006) Effect of rimonabant, a cannabinoid-1 receptor blocker, on weight and cardiometabolic risk factors in overweight or obese patients: RIO-North America: a randomized controlled trial. JAMA 295:761-775.
    • (2006) JAMA , vol.295 , pp. 761-775
    • Pi-Sunyer, F.X.1    Aronne, L.J.2    Heshmati, H.M.3    Devin, J.4    Rosenstock, J.5
  • 27
    • 84891285302 scopus 로고    scopus 로고
    • 6-Alkoxy-5-aryl-3-pyridinecarboxamides, a new series of bioavailable cannabinoid receptor type 1 (CB1) antagonists including peripherally selective compounds
    • Röver S, Andjelkovic M, Bénardeau A, Chaput E, Guba W, Hebeisen P, Mohr S, Nettekoven M, Obst U, and Richter WF et al. (2013) 6-Alkoxy-5-aryl-3-pyridinecarboxamides, a new series of bioavailable cannabinoid receptor type 1 (CB1) antagonists including peripherally selective compounds. J Med Chem 56:9874-9896.
    • (2013) J Med Chem , vol.56 , pp. 9874-9896
    • Röver, S.1    Andjelkovic, M.2    Bénardeau, A.3    Chaput, E.4    Guba, W.5    Hebeisen, P.6    Mohr, S.7    Nettekoven, M.8    Obst, U.9    Richter, W.F.10
  • 29
    • 84869035098 scopus 로고    scopus 로고
    • Probing the interaction of SR141716A with the CB1 receptor
    • Shim JY, Bertalovitz AC, and Kendall DA (2012) Probing the interaction of SR141716A with the CB1 receptor. J Biol Chem 287:38741-38754.
    • (2012) J Biol Chem , vol.287 , pp. 38741-38754
    • Shim, J.Y.1    Bertalovitz, A.C.2    Kendall, D.A.3
  • 30
    • 0038119607 scopus 로고    scopus 로고
    • Homology model of the CB1 cannabinoid receptor: Sites critical for nonclassical cannabinoid agonist interaction
    • Shim JY, Welsh WJ, and Howlett AC (2003) Homology model of the CB1 cannabinoid receptor: sites critical for nonclassical cannabinoid agonist interaction. Biopolymers 71:169-189.
    • (2003) Biopolymers , vol.71 , pp. 169-189
    • Shim, J.Y.1    Welsh, W.J.2    Howlett, A.C.3
  • 32
    • 0035794019 scopus 로고    scopus 로고
    • Inhibitory effects of SR141716A on G-protein activation in rat brain
    • Sim-Selley LJ, Brunk LK, and Selley DE (2001) Inhibitory effects of SR141716A on G-protein activation in rat brain. Eur J Pharmacol 414:135-143.
    • (2001) Eur J Pharmacol , vol.414 , pp. 135-143
    • Sim-Selley, L.J.1    Brunk, L.K.2    Selley, D.E.3
  • 36
    • 23644444304 scopus 로고    scopus 로고
    • Synthesis of long-chain amide analogs of the cannabinoid CB1 receptor antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) with unique binding selectivities and pharmacological activities
    • Thomas BF, Francisco ME, Seltzman HH, Thomas JB, Fix SE, Schulz AK, Gilliam AF, Pertwee RG, and Stevenson LA (2005) Synthesis of long-chain amide analogs of the cannabinoid CB1 receptor antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) with unique binding selectivities and pharmacological activities. Bioorg Med Chem 13:5463-5474.
    • (2005) Bioorg Med Chem , vol.13 , pp. 5463-5474
    • Thomas, B.F.1    Francisco, M.E.2    Seltzman, H.H.3    Thomas, J.B.4    Fix, S.E.5    Schulz, A.K.6    Gilliam, A.F.7    Pertwee, R.G.8    Stevenson, L.A.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.