Structure-activity relationships for serotonin transporter and dopamine receptor selectivity

Medicinal Chemistry

Volumn 5, Issue 3, 2009, Pages 271-278

  Agatonovic Kustrin, Snezana ^a   Davies, Paul ^b   Turner, Joseph V ^c  

^a LA TROBE UNIVERSITY   (Australia)

^b Sowerby Centre for Health Informatics   (United Kingdom)

^c UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

5 HT transporter; ANN; D2 receptor; QSAR; SERT; Theoretical descriptors

Indexed keywords

AMITRIPTYLINE; AMOXAPINE; ANTIDEPRESSANT AGENT; ARIPIPRAZOLE; CHLORPROMAZINE; CITALOPRAM; CLOMIPRAMINE; CLOZAPINE; COCAINE; DESIPRAMINE; DOMPERIDONE; DOPAMINE 2 RECEPTOR; DOXEPIN; DULOXETINE; ESCITALOPRAM; FENFLURAMINE; FLUOXETINE; FLUPENTIXOL; HALOPERIDOL; HYDROGEN; IMIPRAMINE; LIGAND; MIRTAZAPINE; NEFAZODONE; NEUROLEPTIC AGENT; NITROGEN; OLANZAPINE; SEROTONIN TRANSPORTER; TRAZODONE; UNINDEXED DRUG; ANTICONVULSIVE AGENT; DOPAMINE RECEPTOR;

ARTICLE; ARTIFICIAL NEURAL NETWORK; DRUG RECEPTOR BINDING; DRUG SOLUBILITY; DRUG STRUCTURE; MOLECULAR DYNAMICS; NERVE CELL; PREDICTION; PRIORITY JOURNAL; SENSITIVITY ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ENZYME SPECIFICITY; HUMAN; METABOLISM; MOOD DISORDER; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTICONVULSANTS; ANTIPSYCHOTIC AGENTS; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOOD DISORDERS; NEURAL NETWORKS (COMPUTER); QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, DOPAMINE; SEROTONIN PLASMA MEMBRANE TRANSPORT PROTEINS; SUBSTRATE SPECIFICITY;

EID: 67651171510     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340609788185927     Document Type: Article

References (46)

1. Murray, C.J.; Lopez, A.D. Regional patterns of disability-free life expectancy and disability-adjusted life expectancy: global Burden of Disease Study. Lancet, 1997, 349, 1347-52.
2. Ustun, T.B.; Ayuso-Mateos, J.L.; Chatterji, S.; Mathers, C.; Murray, C.J. Global burden of depressive disorders in the year 2000. Br. J. Psychiatry, 2004, 184, 386-92.
3. Davis, K.L.; Kahn, R.S.; Ko, G.; Davidson, M. Dopamine in schizophrenia: a review and reconceptualization. Am. J. Psychiatry, 1991, 148, 1474-86.
4. Meltzer, H.Y.; Matsubara, S.; Lee, J.C. Classification of typical and atypical antipsychotic drugs on the basis of dopamine D-1, D-2 and serotonin2 pKi values. J. Pharmacol. Exp. Ther., 1989, 251, 238-46.
5. Nyberg, S.; Nakashima, Y.; Nordstrom, A.L.; Halldin, C.; Farde, L. Positron emission tomography of in-vivo binding characteristics of atypical antipsychotic drugs. Review of D2 and 5-HT2 receptor occupancy studies and clinical response. Br. J. Psychiatry Suppl., 1996, 29, 40-4.
6. Remington, G. Understanding antipsychotic "atypicality": a clinical and pharmacological moving target. J. Psychiatry Neurosci., 2003, 28, 275-84.
7. Seeman, P.; Corbett, R.; van Tol, H.H. Atypical neuroleptics have low affinity for dopamine D2 receptors or are selective for D4 receptors. Neuropsychopharmacology, 1997, 16, 93-110.
8. Roth, B.L.; Sheffler, D.; Potkin, S.G. Atypical antipsychotic drug actions: unitary or multiple mechanisms for 'atypicality'? Clin. Neurosci. Res., 2003, 3, 108-17.
9. Taylor, D.M.; Duncan-McConnell, D. Refractory schizophrenia and atypical antipsychotics. J. Psychopharmacol., 2000, 14, 409-18.
10. Coward, D.M. General pharmacology of clozapine. Br. J. Psychiatry Suppl., 1992, 17, 5-11.
11. Roth, B. NIMH Psychoactive Drug Screening Program. http://pdsp.med.unc.edu (14 October 2007).
12. ChemSW Molecular Modeling Pro, 5.1; ChemSW: Fairfield, 2003.
13. StatSoft Inc Statistica Neural Networks, 7.1; StatSoft Inc,: Tulsa, USA, 2005.
14. Turner, J.V.; Maddalena, D.J.; Agatonovic-Kustrin, S. Bioavailability prediction based on molecular structure for a diverse series of drugs. Pharm. Res., 2004, 21, 68-82.
15. Campiani, G.; Butini, S.; Fattorusso, C.; Catalanotti, B.; Gemma, S.; Nacci, V.; Morelli, E.; Cagnotto, A.; Mereghetti, I.; Mennini, T.; Carli, M.; Minetti, P.; Di Cesare, M.A.; Mastroianni, D.; Scafetta, N.; Galletti, B.; Stasi, M.A.; Castorina, M.; Pacifici, L.; Vertechy, M.; Di Serio, S.; Ghirardi, O.; Tinti, O.; Carminati, P. Pyrrolo[1,3]benzothiazepine-based serotonin and dopamine receptor antagonists. Molecular modeling, further structure-activity relationship studies, and identification of novel atypical antipsychotic agents. J. Med. Chem., 2004, 47, 143-57.
16. Talik, P.; Pawłowski, M.; Lasocha, W. The structure of Azo-Analogs of 8-Styrylxanthines- X-Ray and Molecular Modelling Studies. In V Multidyscyplinarna Konferencja Nauki o Leku, Darłówko, 2006.
17. Mager, D.E. Quantitative structure-pharmacokinetic/pharmacodynamic relationships. Adv. Drug Deliv. Rev., 2006, 58, 1326-56.
18. Raevsky, O.A. Physicochemical descriptors in property-based drug design. Mini Rev. Med. Chem., 2004, 4, 1041-52.
19. Turner, J.V.; Maddalena, D.J.; Cutler, D.J. Pharmacokinetic parameter prediction from drug structure using artificial neural networks. Int. J. Pharm., 2004, 270, 209-19.
20. Casarotto, M.G.; Craik, D.J. Ring flexibility within tricyclic antidepressant drugs. J. Pharm. Sci., 2001, 90, 713-21.
21. Kaiser, C.; Setler, P. In Burgers Medicinal Chemistry, Wolff, M.; Ed.: Wiley: New York, 1981; vol. 4, p. 997.
22. Hackling, A.; Ghosh, R.; Perachon, S.; Mann, A.; Holtje, H.D.; Wermuth, C.G.; Schwartz, J.C.; Sippl, W.; Sokoloff, P.; Stark, H. N-(omega-(4-(2-methoxyphenyl)piperazin-1-yl)alkyl)carboxamides as dopamine D2 and D3 receptor ligands. J. Med. Chem., 2003, 46, 3883-99.
23. Smid, P.; Coolen, H.K.; Keizer, H.G.; van Hes, R.; de Moes, J.P.; den Hartog, A.P.; Stork, B.; Plekkenpol, R.H.; Niemann, L.C.; Stroomer, C.N.; Tulp, M.T.; van Stuivenberg, H.H.; McCreary, A.C.; Hesselink, M.B.; Herremans, A.H.; Kruse, C.G. Synthesis, structure-activity relationships, and biological properties of 1-heteroaryl-4-[omega-(1H-indol-3-yl)alkyl]piperazines, novel potential antipsychotics combining potent dopamine D2 receptor antagonism with potent serotonin reuptake inhibition. J. Med. Chem., 2005, 48, 6855-69.
24. Rupp, A.; Kovar, K.A.; Beuerle, G.; Ruf, C.; Folkers, G. A new pharmophoric model for 5-HT reuptake-inhibitors: differentiation of amphetamine analogues. Pharm. Acta Helv., 1994, 68, 235-44.
25. Gundertofte, K.; Bjornholm, B. Pharmacophore mapping of the serotonin reuptake site. Abstr. Pap. Am. Chem. Soc., 1997, 213, 9.
26. Gundertofte, K.; Bogeso, K.P. Development of a pharmacophoric model of the serotonin reuptake site. Abstr. Pap. Am. Chem. Soc., 1994, 27, 163.
27. Bradley, A.L.; Izenwasser, S.; Wade, D.; Klein-Stevens, C.; Zhu, N.; Trudell, M.L. Synthesis and dopamine transporter binding affinities of 3alpha-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1] octanes. Bioorg. Med. Chem. Lett., 2002, 12, 2387-90.
28. Chang, A.S.; Chang, S.M.; Starnes, D.M. Structure-activity relationships of serotonin transport: relevance to nontricyclic antidepressant interactions. Eur. J. Pharmacol., 1993, 247, 239-48.
29. Lindberg, U.H.; Thorberg, S. O.; Bengtsson, S.; Renyi, A.L.; Ross, S.B.; Ogren, S.O. Inhibitors of neuronal monoamine uptake. 2. Selective inhibition of 5-hydroxytryptamine uptake by alpha-amino acid esters of phenethyl alcohols. J. Med. Chem., 1978, 21, 448-56.
30. Smith, D.F. The stereoselectivity of serotonin uptake in brain tissue and blood platelets: the topography of the serotonin uptake area. Neurosci. Biobehav. Rev., 1986, 10, 37-46.
31. Xu, L.; Izenwasser, S.; Katz, J.L.; Kopajtic, T.; Klein-Stevens, C.; Zhu, N.; Lomenzo, S.A.; Winfield, L.; Trudell, M.L. Synthesis and biological evaluation of 2-substituted 3beta-tolyltropane derivatives at dopamine, serotonin, and norepinephrine transporters. J. Med. Chem., 2002, 45, 1203-10.
32. Humber, L.G.; Lee, D.; Rakhit, S.; Treasurywala, A.M. Computer-assisted investigation of structure-activity relationships in serotonin-uptake blockers. J. Mol. Graph., 1985, 3, 84-89.
33. Bureau, R.; Daveu, C.; Lancelot, J.C.; Rault, S. Molecular design based on 3D-pharmacophore. Application to 5-HT subtypes receptors. J. Chem. Inf. Comput. Sci., 2002, 42, 429-36.
34. Quinones-Torrelo, C.; Sagrado, S.; Villanueva-Camanas, R.M.; Medina-Hernandez, M.J. Efficiency of antidepressant drugs as monoamine reuptake inhibitors: analysis of the hydrophobicity influence using biopartitioning micellar chromatographic data. Biomed. Chromatogr., 2004, 18, 427-35.
35. Baumann, P.; Eap, C.B. Enantiomeric antidepressant drugs should be considered on individual merit. Hum. Psychopharmacol., 2001, 16, S85-S92.
36. Lane, R.M.; Baker, G.B. Chirality and drugs used in psychiatry: nice to know or need to know? Cell. Mol. Neurobiol., 1999, 19, 355-72.
37. Baker, G.B.; Prior, T.I. Stereochemistry and drug efficacy and development: relevance of chirality to antidepressant and antipsychotic drugs. Ann. Med., 2002, 34, 537-43.
38. Ballenger, J.C.; Post, R.M. Carbamazepine in manic-depressive illness: a new treatment. Am. J. Psychiatry, 1980, 137, 782-90.
39. Goodnick, P.J. Anticonvulsants in the treatment of bipolar mania. Expert Opin. Pharmacother., 2006, 7, 401-10.
40. Dailey, J.W.; Reith, M.E.; Yan, Q.S.; Li, M.Y.; Jobe, P.C. Anti-convulsant doses of carbamazepine increase hippocampal extracellular serotonin in genetically epilepsy-prone rats: dose response relationships. Neurosci. Lett., 1997, 227, 13-6.
41. Southam, E.; Kirkby, D.; Higgins, G.A.; Hagan, R.M. Lamotrigine inhibits monoamine uptake in vitro and modulates 5-hydroxytryptamine uptake in rats. Eur. J. Pharmacol., 1998, 358, 19-24.
42. Whitton, P.S.; Fowler, L.J. The effect of valproic acid on 5-hydroxytryptamine and 5-hydroxyindoleacetic acid concentration in hippocampal dialysates in vivo. Eur. J. Pharmacol., 1991, 200, 167-9.
43. Cryan, J.F.; Kaupmann, K. Don't worry 'B' happy!: a role for GABA(B) receptors in anxiety and depression. Trends Pharmacol. Sci., 2005, 26, 36-43.
44. Slattery, D.A.; Desrayaud, S.; Cryan, J.F. GABAB receptor antagonist-mediated antidepressant-like behavior is seroton-independent. J. Pharmacol. Exp. Ther., 2005, 312, 290-6.
45. Taylor, C.P. Mechanisms of action of gabapentin. Rev. Neurol. (Paris), 1997, 153, S39-45.
46. Gram, L.; Larsson, O.M.; Johnsen, A.; Schousboe, A. Experimental studies of the influence of vigabatrin on the GABA system. Br. J. Clin. Pharmacol., 1989, 27, 13S-17S.