Bis-quinolinium cyclophanes: Toward a pharmacophore model for the blockade of apamin-sensitive SKCa channels in sympathetic neurons

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 16, 2004, Pages 4231-4235

  Galanakis, Dimitrios ^a   Ganellin, C Robin ^b   Chen, Jian Quing ^b   Gunasekera, Diyan ^b   Dunn, Philip M ^b  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Apamin; Centroid; Conformation; Cyclophane; Pharmacophore; Quinolinium; SK3 channel; Synperiplanar

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; CHANNEL GATING; DRUG CONFORMATION; DRUG SCREENING; DRUG SYNTHESIS; MOLECULAR MODEL; PHARMACOPHORE; SYMPATHETIC NERVE CELL;

APAMIN; CALCIUM CHANNELS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NEURONS; QUINOLINES; SYMPATHETIC NERVOUS SYSTEM;

EID: 3142664644     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.06.011     Document Type: Article

References (33)

1. Haylett D.G., Jenkinson D.H. Cook N.S. Potassium Channels. 1990;70-95 Ellis Horwood Limited, Chichester
2. Castle N.A. Perspect. Drug Discov. Des. 15/16:1999;131
3. Wadsworth J.D., Doorty K.B., Strong P.N. J. Biol. Chem. 269:1994;18053
4. Wadsworth J.D., Torelli S., Doorty K.B., Strong P.N. Arch. Biochem. Biophys. 346:1997;151
5. Wadsworth J.D., Doorty K.B., Ganellin C.R., Strong P.N. Biochemistry. 35:1996;7917
6. Dunn P.M., Benton D.C.H., Campos Rosa J., Ganellin C.R., Jenkinson D.H. Br. J. Pharmacol. 117:1996;35
7. Kohler M., Hirschberg B., Bond C.T., Kinzie J.M., Marrion N.V., Maylie J., Adelman J.P. Science. 273:1996;1709
8. Chandy K.G., Fantino E., Wittekindt O., Kalman K., Tong L.L., Ho T.H., Gutman G.A., Crocq M.A., Ganguli R., Nimgaonkar V., Morris-Rosendahl D.J., Gargus J.J. Mol. Psychiatry. 3:1998;32
9. Banks B.E.C., Brown C., Burgess G.M., Burnstock G., Claret M., Cocks T.M., Jenkinson D.H. Nature. 282:1979;415
10. Burgess G.M., Claret M., Jenkinson D.H. J. Physiol. (Lond.). 317:1981;67
11. Lazdunski M. Cell Calcium. 4:1983;421
12. Gater P.R., Haylett D.G., Jenkinson D.H. Br. J. Pharmacol. 86:1985;861
13. Murphy M.E., Brayden J.E. J. Physiol. (Lond.). 489:1995;723
14. Renaud J.F., Desnuelle C., Schmid-Antomarchi H., Hugues M., Serratrice G., Lazdunski M. Nature. 319:1986;678
15. Behrens M.I., Vergara C. Am. J. Physiol. 263:1992;C794
16. Behrens M.I., Jalil P., Serani A., Vergara F., Alvarez O. Muscle Nerve. 17:1994;1264
17. Bevan M.D., Wilson C.J. J. Neurosci. 19:1999;7617
18. Messier C., Mourre C., Bontempi B., Sif J., Lazdunski M., Destrade C. Brain Res. 551:1991;322
19. Belcadi-Abbassi W., Destrade C. Neuroreport. 6:1995;1293
20. Benington J.H., Woudenberg M.C., Heller H.C. Brain Res. 692:1995;86
21. Yamamoto H.A., Harris R.A. Eur. J. Pharmacol. 88:1983;357
22. Castle N.A., Haylett D.G., Morgan J.M., Jenkinson D.H. Eur. J. Pharmacol. 236:1993;201
23. Dunn P.M. Eur. J. Pharmacol. 252:1994;189
24. Campos Rosa J., Galanakis D., Ganellin C.R., Dunn P.M., Jenkinson D.H. J. Med. Chem. 41:1998;2
25. Campos Rosa J., Galanakis D., Piergentili A., Bhandari K., Ganellin C.R., Dunn P.M., Jenkinson D.H. J. Med. Chem. 43:2000;420
26. Chen J.Q., Galanakis D., Ganellin C.R., Dunn P.M., Jenkinson D.H. J. Med. Chem. 43:2000;3478
27. Hosseini R., Benton D.C.H., Dunn P.M., Jenkinson D.H., Moss G.W.J. J. Physiol. (Lond.). 535:2001;323
28. Vinter J.G., Davis A., Saunders M.R. J. Comput. Aided Mol. Des. 1:1987;31
29. Morley S.D., Abraham R.J., Haworth I.S., Jackson D.E., Saunders M.R., Vinter J.G. J. Comput. Aided Mol. Des. 5:1991;475
30. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. J. Am. Chem. Soc. 107:1985;3902
31. Granovsky, A. A. http://classic.chem.msu.su/gran/gamess/index.html
32. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.J., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., Montgomery J.A. J. Comput. Chem. 14:1993;1347
33. * single point calculations using PC GAMESS to evaluate the energy of the conformer at the ab initio level