N-type calcium channel blockers: Novel therapeutics for the treatment of pain

Medicinal Chemistry

Volumn 2, Issue 5, 2006, Pages 535-543

  Schroeder, C I ^a   Doering, C J ^b   Zamponi, G W ^b   Lewis, R J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

conotoxin; Neuropathic pain; Small molecule mimetics; Voltage gated calcium channel

Indexed keywords

AM 336; AMINOPIPERIDINE DERIVATIVE; CALCISEPTINE; CALCIUM CHANNEL; CALCIUM CHANNEL BLOCKING AGENT; CALCIUM CHANNEL N TYPE; CILNIDIPINE; CYSTEINE DERIVATIVE; FARNESOL; GABAPENTIN; MORPHINE; NARCOTIC ANALGESIC AGENT; OMEGA CONOTOXIN; OMEGA CONOTOXIN CVID; OMEGA CONOTOXIN GVIA; OMEGA CONOTOXIN MVIIA; PIPERIDINE DERIVATIVE; PRANIDIPINE; SNAIL VENOM; SNX 482; UNCLASSIFIED DRUG; VOLTAGE GATED CALCIUM CHANNEL; ZICONTIDE;

CHRONIC PAIN; DOSE RESPONSE; DRUG DESIGN; DRUG POTENCY; DRUG POTENTIATION; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; DRUG TOLERABILITY; HUMAN; MUSCLE CONTRACTION; NEUROPATHIC PAIN; NEUROTRANSMITTER RELEASE; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; UNSPECIFIED SIDE EFFECT;

ANIMALS; CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS, N-TYPE; HUMANS; PAIN; PEPTIDES; PROTEIN SUBUNITS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33748646783     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340606778250216     Document Type: Review

References (111)

1. Tsien, R.W.; Lipscombe, D.; Madison, D.V.; Bley, K.R.; Fox, A.P. Trends. Neurosci., 1988, 11, 431.
2. Wheeler, D.B.; Randall, A.; Tsien, R.W. Science, 1994, 264, 107.
3. McCleskey, E.W. Curr. Opin. Neurobiol., 1994, 4, 304.
4. Dunlap, K.; Luebke, J.I.; Turner, T.J. Trends. Neurosci., 1995, 18, 89.
5. Dolmetsch, R.E.; Pajvani, U.; Fife, K.; Spotts, J.M.; Greenberg, M.E. Science, 2001, 280, 69.
6. Dolmetsch, R.E. Sci. STKE., 2003, E4.
7. Bean, B.P. Annu. Rev. Physiol., 1989, 51, 367.
8. Hess, P. Annu. Rev. Neurosci., 1990, 13, 337.
9. Ertel, E.A.; Campbell, K.P.; Harpold, M.M.; Hofmann, F.; Mori, Y.; Perez-Reyes, E.; Schwartz, A.; Snutch, T.P.; Tanabe, T.; Birnbaumer, L.; Tsien, R. W.; Catterall, W.A. Neuron, 2000, 25, 533.
10. Tsien, R.W.; Ellinor, P.T.; Horne, W.A. Trends. Pharmacol. Sci., 1991, 12, 349.
11. Doering, C.J.; Zamponi, G.W. J. Bioenerg. Biomembr., 2003, 35, 491.
12. Doyle, D.A.; Morais, C.J.; Pfuetzner, R.A,; Kuo, A.; Gulbis, J.M.; Cohen, S.L.; Chait, B.T.; MacKinnon, R. Science, 1998, 280, 69.
13. Jiang, Y.; Lee, A.; Chen, J.; Ruta, V.; Cadene, M.; Chait, B.T.; MacKinnon, R. Nature, 2003, 423, 33.
14. Catterall, W.A. Annu. Rev. Cell. Dev. Biol., 2000, 16, 521.
15. MacKinnon, R. Science, 2004, 306, 1304.
16. Lipkind, G.M.; Fozzard, H.A. Biochemistry, 2001, 40, 6786.
17. Heinemann, S.H.; Schleif, T.: Mori, Y.; Imoto, K. Braz. J. Med. Biol. Res., 1994, 27, 2781.
18. Stotz, S.C.; Hamid, J.; Spaetgens, R.L.; Jarvis, S.E.; Zamponi, G.W. J. Biol. Chem., 2000, 275, 24575.
19. Liang, H.; DeMaria, C.D.; Erickson, M.G.; Mori, M.X.; Alseikhan, B.A.; Yue, D.T. Neuron, 2003, 39, 951.
20. Stotz, S.C.; Zamponi, G. W. Trends. Neurosci., 2001, 24, 176.
21. Halling, D.B.; Aracena-Parks, P.; Hamilton, S.L. Sci. STKE., 2005, re15.
22. Felix, R. Receptors Channels, 1999, 6, 351.
23. Klugbauer, N.; Lacinova, L.; Marais, E.; Hobom, M.; Hofmann, F. J. Neurosci., 1999, 19, 684.
24. De Jongh, K.S.; Warner, C.; Catterall, W.A. J. Biol. Chem., 1990, 265, 14738.
25. Jay, S.D.; Sharp, A.H.; Kahl, S.D.; Vedvick, T.S.; Harpold, M.M.; Campbell, K.P. J. Biol. Chem., 1991, 266, 3287.
26. Richards, M.W.; Butcher, A.J.; Dolphi, A.C. Trends. Pharmacol. Sci., 2004, 25, 626.
27. Bichet, D.; Cornet, V.; Geib, S.; Carlier, E.; Volsen, S.; Hoshi, T.; Mori, Y.; De Waard, M. Neuron, 2000, 25, 177.
28. Chu, P.J.; Robertson, H.M.; Best, P.M. Gene, 2001, 280, 37.
29. Yasuda, T.; Chen, L.; Barr, W.; McRoy, J.E.; Lewis, R.J.; Adams, D.J.; Zamponi, G.W. Eur. J. Neurosci., 2004, 20, 1.
30. Arikkath, J.; Cambell, K.P. Curr. Opin. Neurobiol., 2003, 13, 298.
31. Augustine, G.J.; Charlton, M.P.; Smith, S.J. Annu. Rev. Neurosci., 1987, 10, 633.
32. Miller, R.J. Science, 1987, 235, 46.
33. Westenbroek, R.E.; Hoskins, L.; Catterall, W.A. J. Neurosci., 1998, 18, 6319.
34. Westenbroek, R.E.; Hell, J.W.; Warner, C.; Dubel, S.J.; Snutch, T.P.; Catterall, W.A. Neuron, 1992, 9, 1099.
35. Takemura, M.; Kiyama, H.; Fukui, H.; Tohyama, M.; Wada, H. Brain Res., 1988, 451, 386.
36. Gohil, K.; Bell. J.R.; Ramachandran, J.; Miljanich, G.P. Brain Res., 1994, 653, 258.
37. Kim, C.; Jun, K.; Lee, T.; Kim, S.S.; McEnery, M.W.; Chin, H.; Kim, H.L.; Park, J.M.; Kim, D.K.; Jun, S.J.; Kim, J.; Shin, H.S. Mol. Cell. Neurosci., 2001, 18, 235.
38. Saegusa, H.; Kurihara, T.; Zong, S.; Kazuno, A.; Matsuda, Y.; Nonaka, T.; Han, W.; Toriyama, H.; Tanabe, T. EMBO J., 2001, 20, 2349.
39. Herlitze, S.; Garcia, D.E.; Mackie, K.; Hille, B.; Scheuer, T.; Catterall, W.A. Nature, 1996, 380, 258.
40. Zhang, J.F.; Ellinor, P.T.; Aldrich, R.W.; Tsien, R.W. Neuron, 1996, 17, 991.
41. Zamponi, G.W.; Snutch, T.P. Curr. Opin. Neurobiol., 1998, 8, 351.
42. Schroeder, C.I.; Lewis, R.J. Mar. Drugs, 2006, 4, 193.
43. Basbaum, A.I. Pain, 1995, 61, 349.
44. Kennedy, C.; Henderson, G. Mol. Pharmacol., 1991, 40, 1000.
45. Kennedy, C.; Henderson, G. Neuroscience, 1992, 49, 937.
46. Tao, P.L.; Lee, C.R.; Law, P.Y.; Loh, H.H. Naunyn Schmiedebergs Arch. Pharmacol., 1993, 348, 504.
47. Scott, D.; Wright, C.; Angus, J. Eur. J. Pharmacol., 2002, 451, 279.
48. Jain, K.K. Expert. Opin. Investig. Drugs, 2000, 9, 2403.
49. Wang, Y.-X.; Gao, D.; Pettus, M.; Phillips, C.; Bowersox, S.S. Pain, 2000, 84, 271.
50. Brose, W.G.; Gutlove, D.P.; Luther, R.R.; Bowersox, S.S.; McGuire, D. Clin. J. Pain., 1997, 13, 256.
51. Suh, H.W.; Song, D.K.; Choi, S., R.; Huh, S.O.; Kim, Y.H. Brain Res., 1997, 767, 144.
52. Basilico, L.; Parolaro, D.; Rubino, T.; Gori, E.; Giagnoni, G. Eur. J. Pharmacol., 1992, 218, 75.
53. Pirec, V.; Laurito, C.E.; Lu, Y.; Yeomans, D.C. Anesth. Analg., 2001, 92, 239.
54. Suematsu, M.; Ohnishi, T.; Shinno, E.; Maeda, S.; Matsumoto, K.; Sakuda, M.; Saito, K. Neurosci. Lett., 1993, 163, 193.
55. Olivera, B.M.; Gray, W.R.; Zeikus, R.; McIntosh, J.M.; Varga, J.; Rivier, J.; de Santos, V.; Cruz, L.J. Science, 1985, 230, 1338.
56. Olivera, B.M.; Miljanich, G.P.; Ramachandran, J.; Adams, M.E. Ann. Rev. Biochem., 1994, 63, 823.
57. Feng, Z.P.; Doering, C.J.; Winkfein, R.J.; Beedle, A.M.; Spafford, J.D.; Zamponi, G.W. J. Biol. Chem., 2003, 278, 20171.
58. Williams, M.E.; Feldman, D.H.; McCue, A.F.; Brenner, R.; Velicelebi, G.; Ellis, S.B.; Harpold, M.M. Neuron, 1992, 8, 71.
59. Vanegas, H.; Schaible, H. Pain, 2000, 85, 9.
60. Bridges, D.; Thompson, S.W.N.; Rice, A.S.C. Br. J. Anaesth., 2001, 87, 12.
61. Prado, W.A. J. Med. Biol. Res., 2001, 34, 449.
62. Ellinor, P.T.; Zhang, J.F.; Horne, W.A.; Tsien, R.W. Nature, 1994, 372, 272.
63. Vega, T.; De Pascual, R.; Bulbena, O.; Garcia, A.G. Eur. J. Pharmacol., 1995, 276, 231.
64. Pin, J.P.; Bockaert, J. Eur. J. Pharmacol., 1990, 188, 81.
65. Wang, Y.X.; Pettus, M.; Gao, D.; Phillips, C.; Scott Bowersox, S. Pain, 2000, 84, 151.
66. Heading, C. Curr. Opin. CPNS Investig. Drugs, 1999, 1, 153.
67. Wermeling, D.P.; Berger, J.R. Pharmacotherapy, 2006, 26, 395.
68. Miljanich, G.P. In Venoms to Drugs 2005. Heron Island, Australia, 2005.
69. Wermeling, D.P. Pharmacotherapy, 2005, 25, 1084.
70. Adams, D.J.; Smith, A.B.; Schroeder, C.I.; Yasuda, T.; Lewis, R.J. J. Biol. Chem., 2003, 278, 4057.
71. Lewis, R.J.; Nielsen, K.J.; Craik, D.J.; Loughnan, M.L.; Adams, D.A.; Sharpe, I.A.; Luchian, T.; Adams, D.J.; Bond, T.; Thomas, L.; Jones, A.; Matheson, J.L.; Drinkwater, R.; Andrews, P.R.; Alewood, P.F. J. Biol. Chem., 2000, 275, 35335.
72. Cousins, M.J.; Cjoucke, R.C.; Cher, C.M.; Brooker, C.D.; Amor, P.E.; Crump, D.E. In 10th World Congress of Pain. IASP Press, 2002.
73. Smith, M.T.; Cabot, P.J.; Ross, F.B.; Robertson, A.D.; Lewis, R.J. Pain, 2002, 96, 119.
74. Nadasdi, L.; Yamashiro, D.; Chung, D.; Tarczy-Hornoch, K.; Adriaenssens, P.; Ramachandran, J. Biochemistry, 1995, 34, 8076.
75. Kim, J.I.; Takahashi, M.; Ogura, A.; Kohno, T.; Kudo, Y.; Sato, K. J. Biol. Chem., 1994, 269, 23876.
76. Kim, J.I.; Takahashi, M.; Ohtake, A.; Wakamiya, A.; Sato, K. Biochem. Biophys. Res. Commun., 1995, 206, 449.
77. Lew, M.J.; Flinn, J.P.; Pallaghy, P.K.; Murphy, R.; Whorlow, S.L.; Wright, C.E.; Norton, R.S.; Angus, J.A. J. Biol. Chem., 1997, 272, 12014.
78. Miljanich, G.P.; Bowersox, S.S.; Fox, A.F.; Valentino, K.L.; Yamashiro, D.H. International patent application no, PCT/US96 09766; Classification, C07K 7/10, A61K 37/02, 1993.
79. Flinn, J.P.; Pallaghy, P.K.; Lew, M.J.; Murphy, R.; Angus, J.A.; Norton, R.S. Eur. J. Biochem., 1999, 262, 447.
80. Schroeder, T.; Nielsen, K.J.; Adams, D.A.; Thomas, L.; Loughnan, M.L.; Alewood, P.F.; Lewis, R.J.; Craik, D.J. In 26th annual Lorne conference on protein structure and function, Lorne, Australia, 2001.
81. Pallaghy, P.K.; Norton, R.S. J. Pept. Res., 1999, 53, 343.
82. Schroeder, C.I.; Smythe, M.L.; Lewis, R.J. Molec. Diversity, 2004, 8, 127.
83. Pallaghy, P.K.; Norton, R.S. Biopolymers, 2000, 54, 173.
84. Baell, J.B.; Duggan, P.J.; Forsyth, S.A.; Lewis, R.J.; Lok, Y.P.; Schroeder, C.I. Bioorg. Med. Chem., 2004, 12, 4025.
85. Feng, Z.P.; Hamid, J.; Doering, C.; Bosey, G.M.; Snutch, T.P.; Zamponi, G.W. J. Biol. Chem., 2001, 276, 15728.
86. McDonough, S.I.; Mintz, I.M.; Bean, B.P. Soc. Neurosci., 1995, 21, 1409.
87. Wakamori, M.; Strobeck, M.; Niidome, T.; Teramoto, T.; Imoto, K.; Mori, Y. J. Neurophysiol., 1998, 79, 622.
88. Liu, Z.; Dai, J.; Dai, L.; Deng, M.; Hu, Z.; Hu, W.; Liang, S. J. Biol. Chem., 2006, 281, 8628.
89. Doughty, S.W.; Blaney, F.E.; Orlek, B.S.; Richards, W.G. Prot. Eng., 1998, 11, 95.
90. Feng, Z.P.; Hamid, J.; Doering, C.; Jarvis, S.E.; Bosey, G.M.; Bourinet, E.; Snutch, T.P.; Zamponi, G.W. J. Biol. Chem., 2001, 276, 5726.
91. Kaneko, S.; Cooper, C.B.; Nishioka, N.; Yamasaki, H.; Suzuki, A.; Jarvis, S.E.; Akaike, A.; Satoh, M.; Zamponi, G.W. J. Neurosci., 2002, 22, 82.
92. Roullet, J.B.; Spaetgens, R.; Burlingame, T.; Feng, Z.P.; Zamponi, G.W. J. Biol. Chem., 1999, 274, 25439.
93. Beedle, A.M.; Zamponi, G.W. Biophys. J., 2000, 79, 260.
94. Hu, L.Y.; Ryder TR; Nikam SS; Millerman E; Szoke BG; MF, R. Bioorg. Med. Chem. Lett., 1999, 9, 1121.
95. Winquist, R.J.; Qian Pan, J.; Gribkoff, V.K. Biochem. J., 2005, 70, 489.
96. Seko, T.; Kato, M.; Kohno, H.; Ono, S.; Hashimura, K.; Takenobu, Y.; Takimizu, H.; Nakai, K.; Maegawa, H.; Katsube, N.; Toda, M. Bioorg. Med. Chem. Lett., 2002, 12, 2267.
97. Teodori, E.; Baldi, E.; Dei, S.; Gualtieri, F.; Romanelli, M.N.; Scapecchi, S.; Bellucci, C.; Ghelardini, C.; Matucci, R. J. Med. Chem., 2004, 47, 6070.
98. Murakami, M.; Mori, T.; Nakagawasai, O.; Hagiwara, K.; Sakurada, Y.; Mobarakeh, I.I.; Mrata, A.; Yamadera, F.; Miyoshi, I.; Tan-No, K.; Yanai, K.; Tadano, T.; Iijima, T. Neurosci. Lett., 2004, 367, 118.
99. Nagai, H.; Minatoguchi, S.; Chen, X.H.; Wang, N.; Arai, M.; Uno, Y.; Lu, C.; Misao, Y.; Onogi, H.; Kobayashi, H.; Takemura, G.; Mauyama, R.; Fujiwara, T.; Fujiwara, H. Hypertes. Res., 2005, 28, 361.
100. Weinsberg, F.; Bickmeyer, U.; Wiegand, H. Neuropharmacology, 1994, 33, 885.
101. Gee, N.S.; Brown, J.P.; Dissanayake, V.U.; Offord, J.; Thurlow, R.; Woodruff, G.N. J. Biol. Chem., 1996, 8, 5768.
102. Sutton, K.G.; Martin, D.J.; Pinnock, R.D.; Lee, K.; Scott, R.H. Br. J. Pharmacol., 2002, 135, 257.
103. Allen, J.V.; Horwell, D.C.; Lainton, J.A.; O'Neill, J.A.; Ratcliffe, G.S. Chem. Commun., 1997, 21, 2121.
104. Guo, Z.-X.; Cammidge, A.N.; Horwell, D.C. Tetrahedron, 2000, 56, 5169.
105. Menzler, S.; Bikker, J.A.; Horwell, D.C. Tet. Lett., 1998, 39, 7619.
106. Menzler, S.; Bikker, J.A.; Suman-Chauhan, N.; Horwell, D.C. Bioorg. Med. Chem. Lett., 2000, 10, 345.
107. Ripka, A.S.; Rich, D.H. Curr. Opin. Chem. Biol., 1998, 2, 441.
108. Baell, J.B.; Forsyth, S.A.; Gable, R.W.; Norton, R.S.; Mulder, R.J. J. Comput. Aided. Mol. Des., 2002, 15, 1119.
109. Snutch, T.P.; Feng, Z.P.; Doering, C.; Cayabyab, F.; Janke, D.; Parker, D.B.; Belardetti, F.; Morimoto, B.; Vanderah, T.; Zamponi, G.W. Soc. Neurosci., Session 465.1. 2001.
110. Pallaghy, P.K.; Melnikova, A.P.; Jimenez, E.C.; Olivera, B.M.; Norton, R.S. Biochemistry, 1999, 38, 11553.
111. Stix, G. Sci. Am., 2005, 292, 70.