Characterization of the substituted N-triazole oxindole TROX-1, a small-molecule, state-dependent inhibitor of Ca v2 calcium channels

Molecular Pharmacology

Volumn 81, Issue 3, 2012, Pages 488-497

  Swensen, Andrew M ^a,c   Herrington, James ^a,d   Bugianesi, Randal M ^a   Dai, Ge ^a   Haedo, Rodolfo J ^a,e   Ratliff, Kevin S ^a,f   Smith, McHardy M ^a   Warren, Vivien A ^a,g   Arneric, Stephen P ^b,f   Eduljee, Cyrus ^b   Parker, David ^b   Snutch, Terrance P ^b   Hoyt, Scott B ^a   London, Clare ^a   Duffy, Joseph L ^a   Kaczorowski, Gregory J ^h   McManus, Owen B ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b Zalicus Pharmaceuticals   (Canada)

^c ABBOTT LABORATORIES   (United States)

^d GENENTECH INC   (United States)

^e NANION TECHNOLOGIES GMBH   (Germany)

^f ELI LILLY AND COMPANY   (United States)

^g Koltan Pharmaceuticals   (United States)

^h Kanalis Consulting   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 5 (3 CHLORO 4 FLUOROPHENYL) 3 METHYL 3 (PYRIMIDIN 5 YLMETHYL) 1 (1H 1,2,4 TRIAZO 3 YL) 1,3 DIHYDRO 2H INDOL 2 ONE; CALCIUM; CALCIUM CHANNEL BLOCKING AGENT; CALCIUM CHANNEL N TYPE; INDOLE DERIVATIVE; OMEGA CONOTOXIN MVIIA; TROX 1; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM TRANSPORT; CELL MEMBRANE DEPOLARIZATION; CONTROLLED STUDY; DRUG POTENCY; ELECTRIC POTENTIAL; ELECTROPHYSIOLOGY; FLUORESCENCE; HUMAN; HUMAN CELL; IC 50; MEMBRANE CURRENT; PRIORITY JOURNAL;

CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS, N-TYPE; CELL LINE; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; MEMBRANE POTENTIALS; PATCH-CLAMP TECHNIQUES; TRIAZOLES;

EID: 84863175974     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.111.075226     Document Type: Article

References (40)

1. Abbadie C, McManus OB, Sun SY, Bugianesi RM, Dai G, Haedo RJ, Herrington JB, Kaczorowski GJ, Smith MM, Swensen AM, et al. (2010) Analgesic effects of a substituted N-triazole oxindole (TROX-1), a state-dependent, voltage-gated calcium channel 2 blocker. J Pharmacol Exp Ther 334:545-555.
2. Bean BP (1984) Nitrendipine block of cardiac calcium channels: high-affinity binding to the inactivated state. Proc Natl Acad Sci USA 81:6388-6392.
3. Bezprozvanny I, Scheller RH, and Tsien RW (1995) Functional impact of syntaxin on gating of N-type and Q-type calcium channels. Nature 378:623-626.
4. Bourinet E, Soong TW, Sutton K, Slaymaker S, Mathews E, Monteil A, Zamponi GW, Nargeot J, and Snutch TP (1999) Splicing of alpha 1A subunit gene generates phenotypic variants of P- and Q-type calcium channels. Nat Neurosci 2:407-415. (Pubitemid 30491249)
5. 2+ channels in the rat spinal cord following chronic constrictive nerve injury. Exp Brain Res 147:456-463.
6. Dai G, Haedo RJ, Warren VA, Ratliff KS, Bugianesi RM, Rush A, Williams ME, Herrington J, Smith MM, McManus OB, et al. (2008) A high-throughput assay for evaluating state dependence and subtype selectivity of Cav2 calcium channel inhibitors. Assay Drug Dev Technol 6:195-212. (Pubitemid 351670382)
7. 2+ channel expressed in Xenopus oocytes. J Physiol 485:619-634.
8. Ebersberger A, Portz S, Meissner W, Schaible HG, and Richter F (2004) Effects of N-, P/Q- and L-type calcium channel blockers on nociceptive neurones of the trigeminal nucleus with input from the dura. Cephalalgia 24:250-261. (Pubitemid 38446165)
9. Evans AR, Nicol GD, and Vasko MR (1996) Differential regulation of evoked peptide release by voltage-sensitive calcium channels in rat sensory neurons. Brain Res 712:265-273. (Pubitemid 26106095)
10. Feng ZP, Doering CJ, Winkfein RJ, Beedle AM, Spafford JD, and Zamponi GW (2003) Determinants of inhibition of transiently expressed voltage-gated calcium channels by omega-conotoxins GVIA and MVIIA. J Biol Chem 278:20171-20178. (Pubitemid 36799212)
11. Gohil K, Bell JR, Ramachandran J, and Miljanich GP (1994) Neuroanatomical distribution of receptors for a novel voltage-sensitive calcium-channel antagonist, SNX-230 (ω-conopeptide MVIIC). Brain Res 653:258-266. (Pubitemid 24252847)
12. Hans M, Urrutia A, Deal C, Brust PF, Stauderman K, Ellis SB, Harpold MM, Johnson EC, and Williams ME (1999) Structural elements in domain IV that influence biophysical and pharmacological properties of human alpha1A-containing high-voltage-activated calcium channels. Biophys J 76:1384-1400. (Pubitemid 29262619)
13. 2+ channels. NeuroReport 12:2423-2427.
14. Kim C, Jun K, Lee T, Kim SS, McEnery MW, Chin H, Kim HL, Park JM, Kim DK, Jung SJ, et al. (2001) Altered nociceptive response in mice deficient in the alpha(1B) subunit of the voltage-dependent calcium channel. Mol Cell Neurosci 18:235-245. (Pubitemid 32846531)
15. Kiyonaka S, Wakamori M, Miki T, Uriu Y, Nonaka M, Bito H, Beedle AM, Mori E, Hara Y, De Waard M, et al. (2007) RIM1 confers sustained activity and neurotransmitter vesicle anchoring to presynaptic Ca2+ channels. Nat Neurosci 10: 691-701. (Pubitemid 46828510)
16. Knight YE, Bartsch T, Kaube H, and Goadsby PJ (2002) P/Q-type calcium-channel blockade in the periaqueductal gray facilitates trigeminal nociception: a functional genetic link for migraine? J Neurosci 22:RC213.
17. 2+ channels. Neuroscience 142:823-832.
18. Malmberg AB and Yaksh TL (1995) Effect of continuous intrathecal infusion of omega-conopeptides, N-type calcium-channel blockers, on behavior and antinociception in the formalin and hot-plate tests in rats. Pain 60:83-90.
19. Matsuda Y, Saegusa H, Zong S, Noda T, and Tanabe T (2001) Mice lacking Ca(v)2.3 (alpha1E) calcium channel exhibit hyperglycemia. Biochem Biophys Res Commun 289:791-795. (Pubitemid 34060072)
20. McDonough SI and Bean BP (1998) Mibefradil inhibition of T-type calcium channels in cerebellar purkinje neurons. Mol Pharmacol 54:1080-1087. (Pubitemid 29002052)
21. McGivern JG and McDonough SI (2004) Voltage-gated calcium channels as targets for the treatment of chronic pain. Curr Drug Targets CNS Neurol Disord 3:457-478. (Pubitemid 40081275)
22. Miljanich GP (2004) Ziconotide: neuronal calcium channel blocker for treating severe chronic pain. Curr Med Chem 11:3029-3040.
23. Périer F, Radeke CM, and Vandenberg CA (1994) Primary structure and characterization of a small-conductance inwardly rectifying potassium channel from human hippocampus. Proc Natl Acad Sci USA 91:6240-6244. (Pubitemid 24188319)
24. Pietrobon D (2005) Function and dysfunction of synaptic calcium channels: insights from mouse models. Curr Opin Neurobiol 15:257-265.
25. Saegusa H, Kurihara T, Zong S, Kazuno A, Matsuda Y, Nonaka T, Han W, Toriyama H, and Tanabe T (2001) Suppression of inflammatory and neuropathic pain symptoms in mice lacking the N-type Ca2+ channel. EMBO J 20:2349-2356. (Pubitemid 32452852)
26. Saegusa H, Kurihara T, Zong S, Minowa O, Kazuno A, Han W, Matsuda Y, Yamanaka H, Osanai M, Noda T, et al. (2000) Altered pain responses in mice lacking alpha 1E subunit of the voltage-dependent Ca2+ channel. Proc Natl Acad Sci USA 97:6132-6137. (Pubitemid 30367535)
27. Scott DA, Wright CE, and Angus JA (2002) Actions of intrathecal omega-conotoxins CVID, GVIA, MVIIA, and morphine in acute and neuropathic pain in the rat. Eur J Pharmacol 451:279-286. (Pubitemid 35254031)
28. Snutch TP (2005) Targeting chronic and neuropathic pain: the N-type calcium channel comes of age. NeuroRx 2:662-670.
29. Staats PS, Yearwood T, Charapata SG, Presley RW, Wallace MS, Byas-Smith M, Fisher R, Bryce DA, Mangieri EA, Luther RR, et al. (2004) Intrathecal ziconotide in the treatment of refractory pain in patients with cancer or AIDS: a randomized controlled trial. JAMA 291:63-70. (Pubitemid 38040536)
30. Stocker JW, Nadasdi L, Aldrich RW, and Tsien RW (1997) Preferential interaction of omega-conotoxins with inactivated N-type Ca2+ channels. J Neurosci 17:3002-3013. (Pubitemid 27175814)
31. Thaler C, Gray AC, and Lipscombe D (2004) Cumulative inactivation of N-type CaV2.2 calcium channels modified by alternative splicing. Proc Natl Acad Sci USA 101:5675-5679. (Pubitemid 38481215)
32. 2+ channel subtypes on rat spinal motor neurons, interneurons, and nerve terminals. J Neurosci 18:6319-6330.
33. Williams ME, Brust PF, Feldman DH, Patthi S, Simerson S, Maroufi A, McCue AF, Veliçelebi G, Ellis SB, and Harpold MM (1992) Structure and functional expression of an omega-conotoxin-sensitive human N-type calcium channel. Science 257:389-395.
34. Williams ME, Marubio LM, Deal CR, Hans M, Brust PF, Philipson LH, Miller RJ, Johnson EC, Harpold MM, and Ellis SB (1994) Structure and functional characterization of neuronal alpha 1E calcium channel subtypes. J Biol Chem 269: 22347-22357.
35. Wilson SM, Toth PT, Oh SB, Gillard SE, Volsen S, Ren D, Philipson LH, Lee EC, Fletcher CF, Tessarollo L, et al. (2000) The status of voltage-dependent calcium channels in alpha 1E knock-out mice. J Neurosci 20:8566-8571.
36. Winquist RJ, Pan JQ, and Gribkoff VK (2005) Use-dependent blockade of Cav2.2 voltage-gated calcium channels for neuropathic pain. Biochem Pharmacol 70:489-499. (Pubitemid 40978538)
37. Yamamoto T and Takahara A (2009) Recent updates of N-type calcium channel blockers with therapeutic potential for neuropathic pain and stroke. Curr Top Med Chem 9:377-395.
38. Zamponi GW, Feng ZP, Zhang L, Pajouhesh H, Ding Y, Belardetti F, Pajouhesh H, Dolphin D, Mitscher LA, and Snutch TP (2009) Scaffold-based design and synthesis of potent N-type calcium channel blockers. Bioorg Med Chem Lett 19:6467-6472.
39. Zhang S, Su R, Zhang C, Liu X, Li J, and Zheng J (2008) C101, a novel 4-aminopiperidine derivative selectively blocks N-type calcium channels. Eur J Pharmacol 587:42-47.
40. 2+ channels by SNAP-25, syntaxin and synaptotagmin. Nat Neurosci 2:939-941.