Insights into binding modes of 5-HT2c receptor antagonists with ligand-based and receptor-based methods

Journal of Molecular Modeling

Volumn 17, Issue 10, 2011, Pages 2513-2523

  Lu, Chunhua ^a   Jin, Fangfang ^a   Li, Cui ^a   Li, Weihua ^a   Liu, Guixia ^a   Tang, Yun ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

5 HT2c receptor; 5 HT2c receptor antagonist; Docking; Homology modeling; Pharmacophore

Indexed keywords

ALANINE; ASPARAGINE; CARBONYL DERIVATIVE; HYDROXYL GROUP; LIGAND; NITROGEN; PHENYLALANINE; PIPERIDINE; SEROTONIN 2C ANTAGONIST; VALINE;

ARTICLE; BINDING AFFINITY; CATALYST; COMPARATIVE MOLECULAR FIELD ANALYSIS; HUMAN; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DOCKING; PHARMACOPHORE; PRIORITY JOURNAL;

AMINO ACID SEQUENCE; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN BINDING; RECEPTOR, SEROTONIN, 5-HT2C; REPRODUCIBILITY OF RESULTS; SEQUENCE ALIGNMENT; SEROTONIN 5-HT2 RECEPTOR ANTAGONISTS;

EID: 80255138894     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-010-0936-9     Document Type: Article

References (34)

1. Giovanni GD, Deurwaerdére PD, Mascio MD, Matteo VD, Esposito E, Spampinato U (1999) Seclective blocked of serotonin-2C/2B receptors enhances mesolimbicand mesostriatal dopaminergic funcition: a combined in vivo electrophysiological and microdialysis study. Neuroscience 91:587-597
2. RM Kostrzewa NY Huang JP Kostrzewa R Brus 2007 Modeling tardive dyskinesia: predictive 5-HT2c receptor antagonist treatment Neurotox Res 11 41 50 10.1007/BF03033481 1:CAS:528:DC%2BD2sXktVeqtro%3D
3. R Emsley 2009 Drugs in development for the treatment of schizophrenia Expert Opin Invest Drugs 18 1103 1108 10.1517/13543780903066756 1:CAS:528:DC%2BD1MXosFCmtLw%3D
4. DW Bonhaus KK Weinhardt M Taylor A Desouza PM Mcneeley K Szczepanski DJ Fontana J Trinh RCL DawsonMW LA Flippin RM Eglen 1997 RS-102221: A Novel High Affinity and Selective 5-HT2c Receptor Antagonist Neuropharmacol 36 621 629 10.1016/S0028-3908(97)00049-X 1:CAS:528:DyaK2sXktlSlsbs%3D (Pubitemid 27272107)
5. GA Kennett MD Wood F Bright B Trail G Riley V Holland KY Avenell T Stean N Uptom S Bromidge IT Forbes AM Brown DN Middlemiss TP Blackburn 1997 SB 240284, a selective and brain penetrant 5-HT2c receptor antagonist Neuropharmacol 36 609 620 10.1016/S0028-3908(97)00038-5 1:CAS:528:DyaK2sXktlSmu7Y%3D (Pubitemid 27272106)
6. CJ Goodacre SM Bromidge D Clapham FD King PJ Lovell M Allen LP Campbell V Holland GJ Riley KR Starr BK Trail MD Wood 2005 A series of bisaryl imidazolidin-2-ones has shown to be selective and orally active 5-HT2c receptor antagonists Bioorg Med Chem Lett 15 4989 4993 10.1016/j.bmcl.2005.08.004 1:CAS:528:DC%2BD2MXhtVynu7zN (Pubitemid 41400170)
7. D Hamprecht F Micheli G Tedesco D Donati M Petrone S Terreni M Wood 2007 5-HT2c antagonists based on fused heterotricyclic templates: Design, synthesis and biological evaluation Bioorg Med Chem Lett 17 424 427 10.1016/j.bmcl.2006. 10.034 1:CAS:528:DC%2BD2sXnvFGkuw%3D%3D (Pubitemid 46073752)
8. F Micheli A Pasquarello G Tedesco D Hamprecht G Bonanomi A Checchia A Jaxa Chamiec F Damiani D Silvia D Donati C Gallotti M Petrone M Rinaldi G Riley S Terreni M Wood 2006 Diaryl substituted pyrrolidinones and pyrroones as 5-HT2c inhibitors: Synthesis and biological evaluation Bioorg Med Chem Lett 16 3906 3912 10.1016/j.bmcl.2006.05.034 1:CAS:528:DC%2BD28Xmt1Ggsbo%3D (Pubitemid 43903229)
9. T Lee AJ Robichaud KE Boyle Y Lu DW Robertson KJ Miller LW Fitzgerald DW Robertson KJ Miller LW Fitzgerald JF McElroy BL Largent 2003 Novel, highly potent, selective 5-HT2A/D2 receptor antagonists as potential atypical antipsychotics Bioorg Med Chem Lett 13 767 770 10.1016/S0960-894X(02)01028-4 1:CAS:528:DC%2BD3sXhvV2gtrY%3D (Pubitemid 36298487)
10. JM Bartolomé A Alcudia JI Andrés NM Cid M García A Megens MA Toledo AA Trabanco 2005 Novel 2-N, N-dimethylaminomethyl-2, 3, 3a, 12b-tetrahydrodibenzo-[b, f]furo[2, 3-d]oxepin derivatives displaying combined norepinephrine reuptake inhibition and 5-HT2A/2C receptor antagonism Bioorg Med Chem Lett 15 2898 2901 10.1016/j.bmcl.2005.03.076 (Pubitemid 40732243)
11. AA Tarbanco JM Alonso JI Andrés JM Cid J Fernández L Iturrino A Megens 2004 Synthesis of 2-N, N-Dimethylaminomethyl-2, 3, 3a, 12b-tetrahydrodibenzo-[b, f]furo[2, 3-d]oxepinderivatives as potential anxiolytic agents Chem Pharm Bull 52 262 265 10.1248/cpb.52.262 (Pubitemid 41656762)
12. CM Park SY Kim WY Park NS Park CM Seong 2008 Synthesis and structure-activity relationship of 1H-indole-3-carboxylic acid pyridine-3-ylamides: A novel series of 5-HT2c receptor antagonists Bioorg Med Chem Lett 18 3844 3847 10.1016/j.bmcl.2008.06.064 1:CAS:528:DC%2BD1cXoslertrs%3D
13. ZL Zuo G Chen XM Luo C Puah WL Zhu KX Chen 2007 Pharmacophore-directed homology modeling and molecular dynamics simulation of G protein-coupled receptor: study of possible binding modes of 5-HT2c receptor agonist Acta Biochim Biophys Sin 39 413 422 10.1111/j.1745-7270.2007.00295.x 1:CAS:528:DC%2BD2sXot1KmsLk%3D (Pubitemid 46990232)
14. AR Leach VJ Gillet RA Lewis R Taylor 2010 Three-Dimensional Pharmacophore Methods in Drug Discovery J Med Chem 53 539 558 10.1021/jm900817u 1:CAS:528:DC%2BD1MXht1OktbjP
15. Accelrys Software Inc 2004 Discovery Studio modeling environment, Release 2.1 Accelrys Inc San Diego, CA http://accelrys.com/
16. Accelrys Software Inc (2004) Discovery Studio modeling environment, Release 2.1. Accelrys Inc, San Diego, CA, http://accelrys.com/
17. CATALYST User Guide, Version 4.11 (Software Package) (2005) Accelrys Inc, San Diego, CA. http://accelrys.com/
18. Bromidge SM, Lovell PJ, Moss SF, Serafinowska HT (2002) WO Patent 2002014273
19. V Garzya IT Forbes AD Gribble MS Hadley AP Lightfoot AH Payne AB Smith SE Douglas DG Cooper IG Stansfiele M Meeson EE Dodds DNC Jones M Wood C Reavill CA Scorer A Worby G Riley P Eddershaw C Ioannou D Donati JJ Hagan EA Ratti 2007 Studies towards the identification of a new generation of atypical antipsychotic agents Bioorg Med Chem Lett 17 400 425 10.1016/j.bmcl.2006.10.036 1:CAS:528:DC%2BD2sXnvFGktg%3D%3D (Pubitemid 46073754)
20. M Barceló R Enrique CF Masaguer E Domínguez FM Areias B José MI Loza 2007 Synthesis and binding affinity of new pyrazole and isoxazole derivatives as potential atypical antipsychotics Bioorg Med Chem Lett 17 4873 4877 10.1016/j.bmcl.2007.06.045 (Pubitemid 47187693)
21. MJ Millan A Gobert F Lejeune F Dejeune A Dekeyn A Newman-Tancredi V Pasteau JM Rivet D Cussac 2003 The novel melationin agonist agomelatine (S20098) is an antagonist at 5-hydroxytryptamine2c receptors, blockade of which enhances the activity of frontocortical dopaminergic and adrenergic pathways J Pharmacol Exp Ther 306 954 964 10.1124/jpet.103.051797 1:CAS:528:DC%2BD3sXmvVehtrg%3D (Pubitemid 37025301)
22. BT Shireman CA Dvorak DA Rudolph P Bonaventure D Nepomuceno L Dvorak KL Miller TW Lovenberg NI Carruthers 2008 2-Alkyl-4-aryl-pyrimidine fused heterocycles as selective 5-HT2A antagonists Bioorg Med Chem Lett 18 2103 2108 10.1016/j.bmcl.2008.01.090 1:CAS:528:DC%2BD1cXjtlymurw%3D (Pubitemid 351380859)
23. KD Pierce TJ Furlong LA Selbie J Shine 1992 Biochem Biophys Res Commun 187 86 93 10.1016/S0006-291X(05)81462-7 1:CAS:528:DyaK3sXksVWitrY%3D
24. L Shi JA Javitch 2002 The binding site of aminergic G protein-coupled receptors: the transmembrane segments and second extracellular loop Annu Rev Pharmacol Toxicol 42 437 467 10.1146/annurev.pharmtox.42.091101.144224 1:CAS:528:DC%2BD38XhvFKntrw%3D (Pubitemid 34162546)
25. Choudhary MS, Craigo S, Roth BL (1992) Indentification of receptor domains that modify ligand binding 5-Hydroxytryptamine2 and 5- Hydroxytryptamine1c Serotonin receptors 42:627-633
26. RA Laskowski MW MacArthur DS Moss JM Thomton 1993 PROCHECK: A Program to check the stereochemical quality of protein structures J Appl Crystallogr 26 283 291 10.1107/S0021889892009944 1:CAS:528:DyaK3sXit12lurY%3D
27. Schrödinger Software Inc 2009 Maestro, Release 9.0 Schrödinger Inc, LLC New York, NY http://www.schrodinger.com
28. Schrödinger Software Inc (2009) Maestro, Release 9.0. Schrödinger Inc, LLC, New York, NY, http://www.schrodinger.com
29. D Hampercht F Micheli G Tedesco A Checchia D Donati M Petrone S Terreni M Wood 2007 Isoindolone derivatives, a new class of 5-HT2c antagonists: Synthesis and biological evaluation Bioorg Med Chem Lett 17 428 433 10.1016/j.bmcl.2006. 10.029 (Pubitemid 46073747)
30. G Vriend C Sander 1993 Quality-control of protein models directional atomic contact analysis J Appl Cryst 26 47 60 10.1107/S0021889892008240 1:CAS:528:DyaK3sXpsleqsw%3D%3D (Pubitemid 23611937)
31. L San B Arranz 2008 Agomelatine: A novel mechanism of antidepressant action involving the melatonergic and the serotonergic system Eur Psychiatry 23 396 402 10.1016/j.eurpsy.2008.04.002
32. Bywater RP 2005 Location and nature of the residues important for ligand recognition in G-protein coupled receptors J Mol Recognit 18 60 72 10.1002/jmr.685 (Pubitemid 40059571)
33. M Chrodhary S Craigo BL Roth 1993 A single point mutation (Phe340∈→∈Leu340) of a conserved phenylalanine abolishes 4-[125l] lodo-(1, 5-dimethoxy) phenylisopropylamine and [3H]mesulergine but not [3H]ketanserin binding to 5-hydroxytryptamine2 receptors Am Soc Pharmacol Exp Ther 43 755 761 (Pubitemid 23146275)
34. A Farce S Dilly S Yous P Berthelot P Chavatte 2006 Homology modeling of the serotoninergic 5-HT2c receptor J Enzyme Inhib Med Chem 21 285 292 10.1080/14756360600700608 1:CAS:528:DC%2BD28XosVKntLw%3D (Pubitemid 44083957)