Bis-quinolinium cyclophanes: Highly potent and selective non-peptidic blockers of the apamin-sensitive Ca2+-activated K+ channel

Current Medicinal Chemistry

Volumn 15, Issue 13, 2008, Pages 1305-1315

  Conejo García, Ana ^a   Campos, Joaquín M ^a  

^a Facultad de Farmacia   (Spain)

Author keywords

Antiperiplanar conformations; Apamin; Bis quinolinium compounds; Cyclophanes; Dequalinium; SK3 channel; Small conductance Ca2+ activated K+; Synperiplanar conformations

Indexed keywords

APAMIN; ATRACURIUM; CALCIUM ACTIVATED POTASSIUM CHANNEL; CARBENE; CYCLOPHANE DERIVATIVE; DEQUALINIUM; NITROGEN; PANCURONIUM; POTASSIUM CHANNEL; PYRIDINIUM DERIVATIVE; QUINOLINE DERIVATIVE; TUBOCURARINE CHLORIDE; ALKANE; POTASSIUM CHANNEL BLOCKING AGENT; UCL 1530;

ALCOHOL ABUSE; CONFORMATION; DRUG POTENCY; DRUG STRUCTURE; GASTROINTESTINAL MOTILITY DISORDER; HUMAN; MEMORY DISORDER; MYOTONIC DYSTROPHY; NARCOLEPSY; NONHUMAN; PHARMACOPHORE; REVIEW; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; DRUG ANTAGONISM; ENZYME SPECIFICITY; METABOLISM;

ALKANES; ANIMALS; APAMIN; POTASSIUM CHANNEL BLOCKERS; POTASSIUM CHANNELS, CALCIUM-ACTIVATED; QUINOLINIUM COMPOUNDS; SUBSTRATE SPECIFICITY;

EID: 47249106977     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986708784534983     Document Type: Review

References (63)

1. Wickenden, A.D. Pharmacol. Ther., 2002, 94, 157
2. Haylett, D.G.; Jenkinson, D.H. In Potassium Channels; Cook, N. S. Ed.; Ellis Horwood Ltd.: Chichester, 1990; pp. 70-95.
3. Lazdunski, M.; Romey, G.; Schmid-Antomarchi, J.F.; Renaud, J.F.; Mourre, C.; Hugues, M.; Fosset, M. Handb. Exp. Pharmacol., 1988, 83, 135.
4. Ferrero, J.D.; Cocks, T.; Burnstock, G. Eur. J. Pharmacol., 1980, 63, 295.
5. Brown, C.M.; Burnstock, G. Br. J. Pharmacol., 1981, 73, 617.
6. Gater, P.R.; Haylett, D.G.; Jenkinson, D.H. Br. J. Pharmacol., 1985, 86, 861.
7. Coats, R.A. Br. J. Pharmacol., 1983, 80, 573.
8. Coats, R.A. Br. J. Pharmacol., 1985, 86, 827.
9. Nånberg, E.; Connolly, E.; Nedergaard, J. Biochim. Biophys. Acta, 1985, 844, 42.
10. Nohmi, M.; Kuba, K. Brain Res., 1984, 301, 146
11. Pennefather, P.; Lancaster, B.; Adams, P.R.; Nicoll, R.A. Proc. Natl. Acad. Sci. USA, 1985, 82, 3040.
12. Bourque, C.W.; Brown, D.A. Neurosci. Lett., 1987, 82, 185.
13. Zhang, L.; Kmjevic, K. Neurosci. Lett., 1987, 74, 58.
14. Banks, B.E.C.; Brown, C.; Burgess, G.M.; Burnstock, G.; Claret, M.; Cocks, T.M.; Jenkinson, D.H. Nature, 1979, 282, 415.
15. Burgess, G.M.; Claret, M.; Jenkinson, D.H. J. Physiol. (Lond), 1981, 317, 67.
16. Lazdunski, M. Cell Calcium, 1983, 4, 421.
17. Auguste, P.; Hugues, M.; Grave, B.; Gesquiere, J.-C.; Maes, P.; Tartar, A.; Romey, G.; Schweitz, H.; Lazdunski, M. J. Biol. Chem., 1990, 265, 4753.
18. Zerrouk, H.; Mansuelle, P.; Benslimane, A.; Rochat, H.; Martin-Eauclaire, M. F. FEBS Lett., 1993, 320, 189.
19. Renaud, J.F.; Desnuelle, C.; Schmid-Antomarchi, H.; Hugues, M.; Serratrice, G.; Lazdunski, M. Nature, 1986, 319, 678.
20. Behrens, M.I. Vergara, C. Am. J. Physiol., 1992, 263, C794.
21. Behrens, M.I.; Jalil, P.; Serani, A.; Vergara, F.; Alvarez, O. Muscle Nerve, 1994, 17, 1264.
22. Yamamoto, H.-A.; Harris, R.A. Eur. J. Pharmacol., 1983, 88, 357.
23. Demonchaux, P.; Ganellin, C.R.; Dunn, P.M.; Haylett, D.G.; Jenkinson, D.H. Eur. J. Med. Chem., 1991, 26, 915.
24. Jenkinson, D.H.; Haylett, D.G.; Cook, N.S. Cell Calcium, 1983, 4, 429.
25. Cook, N.S.; Haylett, D.G. J. Physiol., 1985, 358, 373.
26. Castle, N.A.; Haylett, D.G.; Morgan, J.M. Jenkinson, D.H. Eur. J. Pharmacol., 1993, 236, 201.
27. Dunn, P.M. Eur. J. Pharmacol., 1994, 252, 189.
28. Galanakis, D.; Davis, C.A.; Del Rey Herrero, B.; Ganellin, C.R.; Duna, P.M.; Jenkinson, D.H. Bioorg. Med. Chem. Lett., 1995, 5, 559.
29. Galanakis, D.; Calder, J.A.D.; Ganellin, C.R.; Owen, C.S.; Dunn, P.M. J. Med. Chem., 1995, 38, 3536.
30. Galanakis, D.; Ganellin, C.R.; Malik, S.; Dunn, P.M. J. Med. Chem., 1996, 39, 3592.
31. Campos Rosa, J.; Galanakis, D.; Ganellin, C.R.; Dunn, P.M. J. Med. Chem., 1996, 39, 4247.
32. Galanakis, D., Davis, C.A.; Del Rey Herrero, B.; Ganellin, C.R.; Dunn, P.M.; Jenkinson, D.H. J. Med. Chem., 1995, 38, 595.
33. Galanakis, D.; Davis, C.A.; Ganellin, C.R.; Dunn, P.M. J. Med. Chem., 1996, 39, 359.
34. Campos Rosa, J.; Galanakis, D.; Piergentili, A.; Bhandari, K.; Ganellin, C. R.; Dunn, P. M.; Jenkinson, D. H. J. Med. Chem., 2000, 43, 420.
35. Haenel, M.W.; Irngartinger, H.; Krieger, D. Chem. Ber., 1985, 118, 144.
36. Wenner, W. J. Org. Chem., 1952, 17, 523.
37. (a) Szendey, G.L.; Munnes, S. Chem. Ber., 1961, 94 38.
38. (b) Staab, H.A.; Haenel, M. Chem. Ber., 1973, 106, 2190.
39. Cram, D.J.; Steinberg, H. J. Am. Chem. Soc., 1951, 73, 5691.
40. Strekowski, L.; Wilson, W.D.; Mokrosz, J.L.; Mokrosz, M.J.; Harden, D.B.; Tanious, F.A.; Wydra, R.L.; Crow, S.A. J. Med. Chem., 1991, 34, 580.
41. (a) Braun, V. Chem. Ber., 1937, 70, 979.
42. (b) Albert, A.; Mills, J.A.; Royer, R. J. Chem. Soc., 1947, 1452.
43. Vögtle, F.; Neumann, P. Tetrahedron, 1970, 26, 5299.
44. Campos Rosa, J.; Dunn, P.M.; Galanakis, D.; Ganellin, C.R.; Jenkinson, D.H.; Yang, D.; Chen, J. PCT Int. Appl. WO 97 48,705, Dec 24, 1997; Chem. Abstr. 1998, 128, 88792e.
45. (a) Wadsworth, J.D.F.; Doorty, K.B.; Strong, P.N. J. Biol. Chem., 1994, 269, 18053.
46. (b) Wadsworth, J.D.F.; Doorty, K.B.; Ganellin, C.R.; Strong, P.N. Biochemistry, 1996, 35, 7917.
47. Köhler, M.; Hirschberg, B.; Bond, C.T.; Kinzie, J.M.; Marrion, N.V.; Maylie, J.; Adelman, J.P. Science, 1996, 273, 1709.
48. (a) Dunn, P.M.; Campos Rosa, J.; Beckwith-Hall, B.M.; Benton, D.C.; Ayalew, Y.; Ganellin, C.R.; Jenkinson, D.H. Br. J. Pharmacol., 1994, 112, 131P.
49. (b) Dunn, P.M.; Benton, D.C.H.; Campos Rosa, J.; Ganellin, C.R.; Jenkinson, D.H. Br. J. Pharmacol., 1996, 117, 35
50. Dunn, P.M. Eur. J. Pharmacol., 1999, 368, 119.
51. Schmohel, E.; Ott, F.; Breitenbach, J.; Nieger, M.; Vogtle, F. Chem. Ber., 1993, 126, 2477.
52. Paton, W.D.M.; Zaimis, E.J. Br. J. Pharmacol., 1949, 4, 381.
53. Benton, D.C.H.; Dunn, P.M.; Chen, J.Q.; Galanakis, D.; Ganellin, C.R.; Malik-Hall, M.; Shah, M.; Haylett, D.G.; Jenkinson, D.H. Br. J. Pharmacol., 1999, 128, 39P.
54. Rekker, R.F.; de Kort, H.M. Eur. J. Med. Chem., 1979, 14, 479.
55. Chen, J.-Q.; Galanakis, D.; Ganellin, C.R.; Dunn, P.M.; Jenkinson, D.H. J. Med. Chem., 2000, 43, 3478.
56. Campos Rosa, J.; Galanakis, D.; Ganellin, C.R.; Dunn, P.M. Jenkinson, D.H. J. Med. Chem., 1998, 41, 2.
57. Kohler, M.; Hirschberg, B.; Bond, C.T.; Kinzie, J.M.; Marrion, N.V.; Maylie, J.; Adelman, J.P. Science, 1996, 273, 1709.
58. 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, 1998, 3, 32.
59. Hosseini, R.; Benton, D.C.H.; Dunn, P.M.; Jenkinson, D.H.; Moss, G.W. J. Physiol., 2001, 535, 323.
60. Dunn, P.M.; Benton, D.C.H.; Campos Rosa, J.; Ganellin, C.R.; Jenkinson, D.H. Br. J. Pharmacol., 1996, 117, 35.
61. Cook, N.S.; Haylett, D.G. J. Physiol., 1985, 358, 373.
62. Galanakis, D.; Ganellin, C.R. Bioorg. Med. Chem. Lett., 2004, 14, 4031.
63. Galanakis, D.; Ganellin, C.R.; Chen, J.-Q.; Gunasekera, D.; Dunn, P.M. Bioorg. Med. Chem. Lett., 2004, 14, 4231.