Molecular properties of psychopharmacological drugs determining non-competitive inhibition of 5-HT3A receptors

European Journal of Medicinal Chemistry

Volumn 44, Issue 6, 2009, Pages 2667-2672

  Kornhuber, Johannes ^a   Terfloth, Lothar ^b   Bleich, Stefan ^c   Wiltfang, Jens ^d   Rupprecht, Rainer ^e  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b Molecular Networks GmbH   (Germany)

^c HANNOVER MEDICAL SCHOOL   (Germany)

^d UNIVERSITY OF DUISBURG ESSEN   (Germany)

^e UNIVERSITY OF MUNICH   (Germany)

Author keywords

5 HT3 receptor; Antidepressant drugs; Antipsychotic drugs; Lipid rafts; Size intensive descriptors; Structure property activity relationship model

Indexed keywords

10,11 DIHYDROCARBAMAZEPINE; ACRIDINE; ANTIDEPRESSANT AGENT; CARBAMAZEPINE; DESIPRAMINE; DIBENZOSUBERANE; FLUOXETINE; FLUPENTIXOL; FLUPHENAZINE; HALOPERIDOL; IMINODIBENZYLE; IMIPRAMINE; LEVOMEPROMAZINE; MOCLOBEMIDE; NEUROLEPTIC AGENT; PHENOTHIAZINE; REBOXETINE; RISPERIDONE; SEROTONIN 3A ANTAGONIST; SEROTONIN 3A RECEPTOR; SEROTONIN ANTAGONIST; THIORIDAZINE; TRIFLUOROMETHYLPHENOTHIAZINE; TRIMIPRAMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG INHIBITION; DRUG STRUCTURE; LIPID RAFT; MOLECULAR WEIGHT; PSYCHOPHARMACOLOGY; STRUCTURE ACTIVITY RELATION;

BINDING SITES; COMPUTER SIMULATION; DATABASES, FACTUAL; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; PSYCHOTROPIC DRUGS; RECEPTORS, SEROTONIN, 5-HT3; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 64249115642     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.12.003     Document Type: Article

References (60)

1. Barnes N.M., and Sharp T. Neuropharmacology 38 (1999) 1083-1152
2. van Hooft J.A., and Vijverberg H.P.M. Trends. Neurosci. 3 (2000) 605-610
3. Davies P.A., Pistis M., Hanna M.C., Peters J.A., Lambert J.J., Hales T.G., and Kirkness E.F. Nature 397 (1999) 359-363
4. Maricq A.V., Peterson A.S., Brake A.J., Myers R.M., and Julius D. Science 254 (1991) 432-437
5. Dubin A.E., Huvar R., D'Andrea M.R., Pyati J., Zhu J.Y., Joy K.C., Wilson S.J., Galindo J.E., Glass C.A., Luo L., Jackson M.R., Lovenberg T.W., and Erlander M.G. J. Biol. Chem. 274 (1999) 30799-30810
6. Gralla R.J., Itri L.M., Pisko S.E., Squillante A.E., Kelsen D.P., Braun Jr. D.W., Bordin L.A., Braun T.J., and Young C.W. N. Engl. J. Med. 305 (1981) 905-909
7. Rodgers R.J., Cole J.C., and Tredwell J.M. Psychopharmacology (Berl.) 117 (1995) 306-312
8. Zoldan J., Friedberg G., Goldberg-Stern H., and Melamed E. Lancet 341 (1993) 562-563
9. Greenshaw A.J., and Silverstone P.H. Drugs 53 (1997) 20-39
10. Fan P. Neurosci. Lett. 173 (1994) 210-212
11. Eisensamer B., Rammes G., Gimpl G., Shapa M., Ferrari U., Hapfelmeier G., Bondy B., Parsons C., Gilling K., Zieglgänsberger W., Holsboer F., and Rupprecht R. Mol. Psychiatry 8 (2003) 994-1007
12. Rammes G., Eisensamer B., Ferrari U., Shapa M., Gimpl G., Gilling K., Parsons C., Riering K., Hapfelmeier G., Bondy B., Zieglgänsberger W., Holsboer F., and Rupprecht R. Mol. Psychiatry 9 (2004) 846-858
13. Fan P. Br. J. Pharmacol. 112 (1994) 741-744
14. Breitinger H.G., Geetha N., and Hess G.P. Biochemistry 40 (2001) 8419-8429
15. Eisensamer B., Uhr M., Meyr S., Gimpl G., Deiml T., Rammes G., Lambert J.J., Zieglgänsberger W., Holsboer F., and Rupprecht R. J. Neurosci. 25 (2005) 10198-10206
16. In: Todeschini R., and Consonni V. (Eds). Handbook of Molecular Descriptors (2000), Wiley-VCH, Weinheim, Germany
17. Tropsha A., Gramatica P., and Gombar V.K. QSAR Comb. Sci. 22 (2003) 69-77
18. von der Voet H. Chemom. Intell. Lab. Syst. 25 (1994) 313-323
19. Bollinger C.R., Teichgraber V., and Gulbins E. Biochim. Biophys. Acta 1746 (2005) 284-294
20. Gulbins E., and Li P.L. Am. J. Physiol. Regul. Integr. Comp. Physiol. 290 (2006) R11-R26
21. Kornhuber J., Tripal P., Reichel M., Terfloth L., Bleich S., Wiltfang J., and Gulbins E. J. Med. Chem. 51 (2008) 219-237
22. Donati R.J., and Rasenick M.M. Neuropsychopharmacology 30 (2005) 1238-1245
23. Purvis III G.D. J. Comput. Aided Mol. Des. 22 (2008) 461-468
24. Holder A.J., Ye L., Yourtee D.M., Agarwal A., Eick J.D., and Chappelow C.C. Dent. Mater. 21 (2005) 591-598
25. Chen X.Q., Cho S.J., Li Y., and Venkatesh S. J. Pharm. Sci. 91 (2002) 1838-1852
26. Yen T.E., Agatonovic-Kustrin S., Evans A.M., Nation R.L., and Ryand J. J. Pharm. Biomed. Anal. 38 (2005) 472-478
27. González M.P., Helguera A.M., and Collado I.G. Mol. Divers 10 (2006) 109-118
28. Worrall F., and Thomsen M. Chemosphere 54 (2004) 585-596
29. Agatonovic-Kustrin S., Beresford R., and Yusof A.P.M. J. Pharm. Biomed. Anal. 25 (2001) 227-237
30. Lien E.J., Guo Z.-R., Li R.-L., and Su C.-T. J. Pharm. Sci. 71 (1982) 641-655
31. Laguerre M., Dubost J.-P., Kummer E., and Carpy A. Drug Des. Discov. 11 (1994) 205-222
32. Morreale A., Iriepa I., and Gálvez E. Curr. Med. Chem. 9 (2002) 99-125
33. Zhu L.P., Ye D.Y., and Tang Y. J. Mol. Model. 13 (2007) 121-131
34. Glennon R.A., Daoud M.K., Dukat M., Teitler M., Herrick-Davis K., Purohit A., and Syed H. Bioorg. Med. Chem. 11 (2003) 4449-4454
35. Cappelli A., Anzini M., Vomero S., Mennuni L., Makovec F., Doucet E., Hamon M., Menziani M.C., De Benedetti P.G., Giorgi G., Ghelardini C., and Collina S. Bioorg. Med. Chem. 10 (2002) 779-801
36. Li H., Yap C.W., Ung C.Y., Xue Y., Li Z.R., Han L.Y., Lin H.H., and Chen Y.Z. J. Pharm. Sci. 96 (2007) 2838-2860
37. I. Mierswa, M. Wurst, R. Klinkenberg, M. Scholz, T. Euler, YALE: Rapid prototyping for complex data mining tasks, in: Proceedings of the 12th ACM SIGKDD International Conference on Knowledge Discovery and Data Mining (KDD-06), 2006.
38. PubChem-Project National Center for Biotechnology Information USA (2007). http://pubchem.ncbi.nlm.nih.gov Available from:
39. Leo A., Hansch C., and Elkins D. Chem. Rev. 71 (2007) 525-616
40. Ma J.Y.C., Ma J.K.H., and Weber K.C. J. Lipid Res. 26 (1985) 735-744
41. Hansch C., and Dunn III W.J. J. Pharm. Sci. 61 (1972) 1-19
42. Baird C.L., Courtenay E.S., and Myszka D.G. Anal. Biochem 310 (2002) 93-99
43. Ottiger C., and Wunderli-Allenspach H. Eur. J. Pharmac. Sci. 5 (1997) 223-231
44. Ahyayauch H., Goni F.M., and Bennouna M. Int. J. Pharm 279 (2004) 51-58
45. Austin R.P., Davis A.M., and Manners C.N. J. Pharm. Sci. 84 (1995) 1180-1183
46. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 23 (1997) 3-25
47. van de Waterbeemd H., Camenisch G., Folkers G., Chretien J.R., and Raevsky O.A. J. Drug Target. 6 (1998) 151-165
48. Deconinck E., Zhang M.H., Coomans D., and Vander Heyden Y. J. Chem. Inf. Model. 46 (2006) 1410-1419
49. Ertl P., Rohde B., and Selzer P. J. Med. Chem. 43 (2000) 3714-3717
50. Kelder J., Grootenhuis P.D.J., Bayada D.M., Delbressine L.P.C., and Ploemen J.-P. Pharm. Res. 16 (1999) 1514-1519
51. Clark D.E. J. Pharm. Sci. 88 (1999) 815-821
52. Labute P. J. Mol. Graph. Model. 18 (2000) 464-477
53. ACD/LogD Suite Advanced Chemistry Development Inc. (2007). http://www.acdlabs.com Available from:
54. ADRIANA.CODE, Version 2.1 Molecular Networks (2008), GmbH Computerchemie. http://www.molecular-networks.com Available from:
55. DRAGON for Windows (Software for Molecular Descriptor Calculations) Version 5.5 (2007), Talete srl. Available from: http://www.talete.mi.it/
56. In: Breiman L., Friedman J.H., Olshen R.A., and Stone C.J. (Eds). Classification and Regression Trees (1984), Wadsworth International Group, Belmont CA
57. Deconinck E., Hancock T., Coomans D., Massart D.L., and Vander Heyden Y. J. Pharm. Biomed. Anal. 39 (2005) 91-103
58. Bai J.P.F., Utis A., Crippen G., He H.-D., Fischer V., Tullman R., Yin H.-Q., Hsu C.-P., Jiang L., and Hwang K.-K. J. Chem. Inf. Comput. Sci. 44 (2004) 2061-2069
59. Daszykowski M., Walczak B., Xu Q.-S., Daeyaert F., de Jonge M.R., Heeres J., Koymans L.M.H., Lewi P.J., Vinkers H.M., Janssen P.A., and Massart D.L. J. Chem. Inf. Comput. Sci. 44 (2004) 716-726
60. Caetano S., Aires-de-Sousa J., Daszykowski M., and Vander Heyden Y. Anal. Chim. Acta 544 (2005) 315-326