α1 adrenoceptor subtype selectivity - 3D-QSAR models for a new class of α1 adrenoceptor antagonists derived from the novel antipsychotic sertindole

Journal of Molecular Graphics and Modelling

Volumn 21, Issue 6, 2003, Pages 523-534

  Balle, Thomas ^a,b   Andersen, Kim ^a   Søby, Karina Krøjer ^a   Liljefors, Tommy ^b  

^a H LUNDBECK A S   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

3D QSAR; Antipsychotic; GOLPE; GRID; Sertindole; Subtype selectivity; 1 Adrenoceptor antagonist

Indexed keywords

BINDING ENERGY; ELECTROSTATICS; MOLECULAR GRAPHICS; PROBES; STATISTICAL METHODS;

RECEPTOR-BINDING;

MOLECULAR BIOLOGY;

ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 1 ADRENERGIC RECEPTOR BLOCKING AGENT; INDOLE; METHYL GROUP; NEUROLEPTIC AGENT; RECEPTOR SUBUNIT; SERTINDOLE; WATER;

ARTICLE; BRAIN MEMBRANE; DRUG RECEPTOR BINDING; ELECTRICITY; MOLECULAR MODEL; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEPTOR AFFINITY;

EID: 0037409340     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1093-3263(03)00120-7     Document Type: Article

References (41)

1. 1 adrenoceptors: consensus update. Pharmacol. Rev. 47:1995;267-270.
2. 1 Adrenoceptor subtypes. Eur. J. Pharmacol. 375:1999;261-276.
3. 1 adrenoceptor radioligand to rat and human tissues Eur. J. Pharmacol. 348:1998;287-295.
4. De Paermentier F., Mauger J.M., Lowther S., Crompton M.R., Katona C.L., Horton R.W. Brain α adrenoceptors in depressed suicides. Brain Res. 757:1997;60-68.
5. 1 Adrenoceptor subtypes: a synopsis of their pharmacology and molecular biology. Drug Dev. Res. 39:1996;54-107.
6. Ruffolo R.R. Jr., Bondinell W., Hieble J.P. α and β adrenoceptors: from the gene to the clinic. 2. Structure-activity relationships and therapeutic applications. J. Med. Chem. 38:1995;3681-3716.
7. Hieble J.P., Bondinell W.E., Ruffolo R.R. Jr. α and β adrenoceptors: from the gene to the clinic. 1. Molecular biology and adrenoceptor subclassification. J. Med. Chem. 38:1995;3415-3444.
8. 1a adrenoceptor selective antagonists for the treatment of benign prostatic hyperplasia. Drugs Future. 26:2001;757-765.
9. Kenny B., Ballard S., Blagg J., Fox D. Pharmacological options in the treatment of benign prostatic hyperplasia. J. Med. Chem. 40:1997;1293-1315.
10. Baldessarini R.J., Huston-Lyons D., Campbell A., Marsh E., Cohen B.M. Do central antiadrenergic actions contribute to the atypical properties of clozapine? Br. J. Psychiatry Suppl. 17:1992;12-16.
11. Lipinski J.F.J., Cohen B.M., Zubenko G.S., Waternaux C.M. Adrenoceptors and the pharmacology of affective illness: a unifying theory. Life Sci. 40:1987;1947-1963.
12. Holz W.C., Hieble J.P., Gill C.A., Demarinis R.M., Pendleton R.G. α Adrenergic agents. 3. Behavioral effects of 2-aminotetralins. Psychopharmacology. 77:1982;259-267.
13. Arnt J., Skarsfeldt T. Do novel antipsychotics have similar pharmacological characteristics? A review of the evidence. Neuropsychopharmacology. 18:1998;63-101.
14. Prinssen E.P., Ellenbroek B.A., Cools A.R. Combined antagonism of adrenoceptors and dopamine and 5-HT receptors underlies the atypical profile of clozapine. Eur. J. Pharmacol. 262:1994;167-170.
15. Rao T.S., Contreras P.C., Cler J.A., Emmett M.R., Mick S.J., Iyengar S., Wood P.L. Clozapine attenuates N-methyl-D-aspartate receptor complex-mediated responses in vivo: tentative evidence for a functional modulation by a noradrenergic mechanism. Neuropharmacology. 30:1991;557-565.
16. 1 noradrenergic receptors demonstrated by in vivo voltammetry. Brain Res. 460:1988;398-401.
17. 1 adrenoceptor antagonist prazosin and the dopamine D2 receptor antagonist raclopride in rats. J. Neural Transm. 107:2000;1229-1238.
18. 1a adrenoceptors in rat mesenteric small arteries. Eur. J. Pharmacol. 336:1997;29-35.
19. 1 adrenoceptor antagonists. J. Med. Chem. 46:2003;265-283.
20. 1 adrenoceptor antagonists, Bioorg. Med. Chem., DOI: 10.1016/S0968-0896(02)00459-5.
21. Goodford P.J. A computational procedure for determining energetically favorable binding sites on biologically important macromolecules. J. Med. Chem. 28:1985;849-857.
22. GRID, Molecular Discovery Ltd., Oxford, UK, 1998.
23. Baroni M., Constantino G., Cruciani G., Riganelli D., Valigi R., Clementi S. Generating optimal linear PLS estimations (GOLPE): an advanced chemometric tool for handling 3D-QSAR problems. Quant. Struct. Act. Relat. 12:1993;9-20.
24. GOLPE 4.5, Multivariate Infometric Analyses, Viale del Castagni 16, Perugia, Italy, 1999.
25. Cruciani G., Watson K.A. Comparative molecular field analysis using GRID force-field and GOLPE variable selection methods in a study of inhibitors of glycogen phosphorylase b. J. Med. Chem. 37:1994;2589-2601.
26. 1a adrenergic antagonists. J. Mol. Struct. (Theochem.). 280:1993;283-290.
27. 1 Adrenoceptor subtype selectivity: molecular modelling and theoretical quantitative structure-affinity relationships. Bioorg. Med. Chem. 5:1997;809-816.
28. 1 adrenergic receptor antagonists. Bioorg. Med. Chem. 7:1999;2437-2451.
29. 1 adrenoceptor antagonists. J. Med. Chem. 44:2001;2403-2410.
30. 1b adrenergic receptor is a key switch residue involved in activation and catecholamine ring aromatic bonding. J. Biol. Chem. 274:1999;16320-16330.
31. 1 adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists. J. Biol. Chem. 276:2001;25366-25371.
32. 1a adrenergic receptors. J. Biol. Chem. 275:2000;11698-11705.
33. 1 Adrenergic receptors: new insights and directions. J. Pharmacol. Exp. Ther. 298:2001;403-410.
34. Lapinsh M., Prusis P., Gutcaits A., Lundstedt T., Wikberg J.E. Development of proteo-chemometrics: a novel technology for the analysis of drug-receptor interactions. Biochim. Biophys. Acta. 1525:2001;180-190.
35. 2 antagonists within a series of 3-substituted 1-(4-fluorophenyl)-1H-indoles. J. Med. Chem. 35:1992;1092-1101.
36. 2 antagonists. 1. 2- and 6-substituted 1-phenyl-3-(4-piperidinyl)-1H-indoles. J. Med. Chem. 35:1992;4813-4822.
37. J. Perregaard, B. Costall, Treatment of cognitive disorders, Patent no. PCT/DK92/00063 (WO 92/15303) (1992).
38. J. Perregaard, H. Pedersen, K. Andersen, K.P. Bøgesø, Novel indole derivatives, Patent no. 91610055.5 (EP 0 465 398 B1) (1994).
39. Halgren T.A. J. Comput. Chem. 17:1996;490-641. (Five papers).
40. Mohamadi F., Richards N.G., Gouida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. MacroModel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11:1990;440-467.
41. Pastor M., Cruciani G., Clementi S. Smart region definition: a new way to improve the predictive ability and interpretability of three-dimensional quantitative structure-activity relationships. J. Med. Chem. 40:1997;1455-1464.