Inhibition of N-type calcium channels by fluorophenoxyanilide derivatives

Marine Drugs

Volumn 13, Issue 4, 2015, Pages 2030-2045

  Gleeson, Ellen C ^a,b   Graham, Janease E ^a,b   Spiller, Sandro ^a,e   Vetter, Irina ^c   Lewis, Richard J ^c   Duggan, Peter J ^b,d   Tuck, Kellie L ^a  

^a MONASH UNIVERSITY   (Australia)

^b CSIRO   (Australia)

^c UNIVERSITY OF QUEENSLAND   (Australia)

^d FLINDERS UNIVERSITY   (Australia)

^e UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Cav2.2; Channel blocker; FLIPR; N type calcium channel; Pain

Indexed keywords

4 (3 AMINOPROPOXY) N [2 (4 FLUOROPHENOXY)PHENYL]BENZAMIDE; 4 (3 AMINOPROPOXY) N [3 (4 FLUOROPHENOXY)PHENYL]BENZAMIDE; 4 (3 AMINOPROPOXY) N [4 (4 FLUOROPHENOXY)PHENYL]BENZAMIDE; ANALGESIC AGENT; CALCIUM CHANNEL; CALCIUM CHANNEL BLOCKING AGENT; CALCIUM CHANNEL CAV2.2; CALCIUM CHANNEL N TYPE; CALCIUM ION; FLUOROPHENOXYANILIDE DERIVATIVE; N [2 (4 FLUOROPHENOXY)PHENYL] 4 (3 GUANIDINOPROPOXY)BENZAMIDE HYDROCHLORIDE; N [3 (4 FLUOROPHENOXY)PHENYL] 4 (3 GUANIDINOPROPOXY)BENZAMIDE HYDROCHLORIDE; N [4 (4 FLUOROPHENOXY)PHENYL] 4 (3 GUANIDINOPROPOXY)BENZAMIDE HYDROCHLORIDE; UNCLASSIFIED DRUG; ANILIDE; CACNA1B PROTEIN, HUMAN; FLUOROBENZENE; NERVE PROTEIN; NEUROTOXIN; OMEGA CONOTOXIN GVIA;

ARTICLE; BIOASSAY; CHANNEL INHIBITION; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENT PLATE READER ASSAY; IC50; MOLECULAR WEIGHT; NEUROBLASTOMA CELL LINE; SH SY5Y CELL LINE; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; BINDING COMPETITION; CALCIUM SIGNALING; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; HIGH THROUGHPUT SCREENING; HUMAN; METABOLISM; MOLECULARLY TARGETED THERAPY; NERVE CELL; NEURALGIA; PAIN, INTRACTABLE; SYNTHESIS; TUMOR CELL LINE;

ANALGESICS, NON-NARCOTIC; ANILIDES; BINDING, COMPETITIVE; CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS, N-TYPE; CALCIUM SIGNALING; CELL LINE, TUMOR; DRUG DESIGN; FLUOROBENZENES; HIGH-THROUGHPUT SCREENING ASSAYS; HUMANS; MOLECULAR STRUCTURE; MOLECULAR TARGETED THERAPY; NERVE TISSUE PROTEINS; NEURALGIA; NEURONS; NEUROTOXINS; OMEGA-CONOTOXIN GVIA; PAIN, INTRACTABLE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84928342358     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md13042030     Document Type: Article

References (45)

1. Vink, S.; Alewood, P.F. Targeting voltage-gated calcium channels: Developments in peptide and small-molecule inhibitors for the treatment of neuropathic pain. Br. J. Pharmacol. 2012, 167, 970-989.
2. 2+ channels to treat pain: T-type versus N-type. Trends Pharmacol. Sci. 2004, 25, 465-470.
3. Lee, M.S. Chapter four - Recent progress in the discovery and development of N-type calcium channel modulators for the treatment of pain. In Progress in Medicinal Chemistry; Lawton, G., Witty, D.R., Eds.; Elsevier: Oxford, UK, 2014; Volume 53, pp. 147-186.
4. Perret, D.; Luo, Z.D. Targeting voltage-gated calcium channels for neuropathic pain management. NeuroRX 2009, 6, 679-692.
5. Pope, J.E.; Deer, T.R. Ziconotide: A clinical update and pharmacologic review. Exp. Opin. Pharmacother. 2013, 14, 957-966.
6. Bear, B.; Asgian, J.; Termin, A.; Zimmermann, N. Small molecules targeting sodium and calcium channels for neuropathic pain. Curr. Opin. Drug Discov. Dev. 2009, 12, 543-561.
7. Yamamoto, T.; Takahara, A. Recent updates of N-type calcium channel blockers with therapeutic potential for neuropathic pain and stroke. Curr. Top. Med. Chem. 2009, 9, 377-395.
8. Zamponi, G.W.; Feng, Z.-P.; Zhang, L.; Pajouhesh, H.; Ding, Y.; Belardetti, F.; Pajouhesh, H.; Dolphin, D.; Mitscher, L.A.; Snutch, T.P. Scaffold-based design and synthesis of potent N-type calcium channel blockers. Bioorg. Med. Chem. Lett. 2009, 19, 6467-6472.
9. Abbadie, C.; McManus, O.B.; Sun, S.-Y.; Bugianesi, R.M.; Dai, G.; Haedo, R.J.; Herrington, J.B.; Kaczorowski, G.J.; Smith, M.M.; Swensen, A.M.; et al. Analgesic effects of a substituted N-triazole oxindole (Trox-1), a state-dependent, voltage-gated calcium channel 2 blocker. J. Pharmacol. Exp. Ther. 2010, 334, 545-555.
10. Pajouhesh, H.; Feng, Z.-P.; Ding, Y.; Zhang, L.; Pajouhesh, H.; Morrison, J.-L.; Belardetti, F.; Tringham, E.; Simonson, E.; Vanderah, T.W.; et al. Structure-activity relationships of diphenylpiperazine N-type calcium channel inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 1378-1383.
11. v2.2) blocker for the treatment of pain. Bioorg. Med. Chem. Lett. 2011, 21, 869-873.
12. Yamamoto, T.; Ohno, S.; Niwa, S.; Tokumasu, M.; Hagihara, M.; Koganei, H.; Fujita, S.-I.; Takeda, T.; Saitou, Y.; Iwayama, S.; et al. Asymmetric synthesis and biological evaluations of (+)- and (-)-6-dimethoxymethyl-1,4-dihydropyridine-3-carboxylic acid derivatives blocking N-type calcium channels. Bioorg. Med. Chem. Lett. 2011, 21, 3317-3319.
13. 2+ channel blockers with analgesic activity. Bioorg. Med. Chem. 2012, 20, 4128-4139.
14. Scott, V.E.; Vortherms, T.A.; Niforatos, W.; Swensen, A.M.; Neelands, T.; Milicic, I.; Banfor, P.N.; King, A.; Zhong, C.; Simler, G.; et al. A-1048400 is a novel, orally active, state-dependent neuronal calcium channel blocker that produces dose-dependent antinociception without altering hemodynamic function in rats. Biochem. Pharmacol. 2012, 83, 406-418.
15. Subasinghe, N.L.; Wall, M.J.; Winters, M.P.; Qin, N.; Lubin, M.L.; Finley, M.F.A.; Brandt, M.R.; Neeper, M.P.; Schneider, C.R.; Colburn, R.W.; et al. A novel series of pyrazolylpiperidine N-type calcium channel blockers. Bioorg. Med. Chem. Lett. 2012, 22, 4080-4083.
16. v2.2 channel inhibitors for the treatment of chronic pain. J. Med. Chem. 2012, 55, 9847-9855.
17. Pajouhesh, H.; Feng, Z.-P.; Zhang, L.; Pajouhesh, H.; Jiang, X.; Hendricson, A.; Dong, H.; Tringham, E.; Ding, Y.; Vanderah, T.W.; et al. Structure-activity relationships of trimethoxybenzyl piperazine N-type calcium channel inhibitors. Bioorg. Med. Chem. Lett. 2012, 22, 4153-4158.
18. Beebe, X.; Yeung, C.M.; Darczak, D.; Shekhar, S.; Vortherms, T.A.; Miller, L.; Milicic, I.; Swensen, A.M.; Zhu, C.Z.; Banfor, P.; et al. Synthesis and SAR of 4-aminocyclopentapyrrolidines as orally active N-type calcium channel inhibitors for inflammatory and neuropathic pain. Bioorg. Med. Chem. Lett. 2013, 23, 4857-4861.
19. Borzenko, A.; Pajouhesh, H.; Morrison, J.-L.; Tringham, E.; Snutch, T.P.; Schafer, L.L. Modular, efficient synthesis of asymmetrically substituted piperazine scaffolds as potent calcium channel blockers. Bioorg. Med. Chem. Lett. 2013, 23, 3257-3261.
20. v2.2 channel inhibitors through a gem-dimethylsulfone bioisostere replacement of a labile sulfonamide. ACS Med. Chem. Lett. 2013, 4, 1064-1068.
21. 2+ channel blocker, A-1264087, utilizes peripheral and spinal mechanisms to inhibit spinal nociceptive transmission in a rat model of neuropathic pain. J. Neurophysiol. 2014, 111, 394-404.
22. 2+ channel blocker that reduces nociception in rat preclinical pain models. J. Pain 2014, 15, 387.e1-387.e14.
23. v2.2 blocker multitarget ligands. Chem. Biol. Drug Des. 2014, doi:10.1111/cbdd.12479.
24. v2.2 binding data for non-peptide mimetics of ω-conotoxin GVIA based on a 5-amino-anthranilamide core. Aust. J. Chem. 2008, 61, 11-15.
25. Andersson, A.; Baell, J.B.; Duggan, P.J.; Graham, J.E.; Lewis, R.J.; Lumsden, N.G.; Tranberg, C.E.; Tuck, K.L.; Yang, A. ω-Conotoxin GVIA mimetics based on an anthranilamide core: Effect of variation in ammonium side chain lengths and incorporation of fluorine. Bioorg. Med. Chem. 2009, 17, 6659-6670.
26. Baell, J.B.; Duggan, P.J.; Forsyth, S.A.; Lewis, R.J.; Lok, Y.P.; Schroeder, C.I. Synthesis and biological evaluation of nonpeptide mimetics of ω-conotoxin GVIA. Bioorg. Med. Chem. 2004, 12, 4025-4037.
27. Baell, J.B.; Duggan, P.J.; Forsyth, S.A.; Lewis, R.J.; Lok, Y.P.; Schroeder, C.I.; Shepherd, N.E. Synthesis and biological evaluation of anthranilamide-based non-peptide mimetics of ω-conotoxin GVIA. Tetrahedron 2006, 62, 7284-7292.
28. Duggan, P.J.; Lewis, R.J.; Lok, Y.P.; Lumsden, N.G.; Tuck, K.L.; Yang, A. Low molecular weight non-peptide mimics of ω-conotoxin GVIA. Bioorg. Med. Chem. Lett. 2009, 19, 2763-2765.
29. v2.2 ion channels. Mar. Drugs 2012, 10, 2349-2368.
30. Press release investors and media - zalicus. Available online: http://phx.corporate-ir.net/phoenix. zhtml?c=148036&p=irol-newsArticle&ID=1874737&highlight= (accessed on 30 January 2015).
31. Lauri, G.; Bartlett, P. Caveat: A program to facilitate the design of organic molecules. J. Comput. -Aided. Mol. Des. 1994, 8, 51-66.
32. Baell, J.; Forsyth, S.; Gable, R.; Norton, R.; Mulder, R. Design and synthesis of type-III mimetics of ω-conotoxin GVIA. J. Comput. Aided. Mol. Des. 2001, 15, 1119-1136.
33. Aguilar, M.-I.; Purcell, A.W.; Devi, R.; Lew, R.; Rossjohn, J.; Smith, A.I.; Perlmutter, P. β-amino acid-containing hybrid peptides-new opportunities in peptidomimetics. Org. Biomol. Chem. 2007, 5, 2884-2890.
34. Wen, F.; Zhang, H.; Yu, Z.; Jin, H.; Yang, Q.; Hou, T. Design, synthesis and antifungal/insecticidal evaluation of novel nicotinamide derivatives. Pestic. Biochem. Physiol. 2010, 98, 248-253.
35. Bertrand, I.; Capet, M.; Lecomte, J.-M.; Levoin, N.; Ligneau, X.; Poupardin-Olivier, O.; Robert, P.; Schwartz, J.-C.; Labeeuw, O. Preparation of pyrrolidinyl- and piperidinylpropoxyarenes as histamine H3 receptor ligands. WO2006117609 A2, France, 9 November 2006.
36. Genzer, J.D.; Huttrer, C.P.; Wessem, G.C.V. Phenoxy- and benzyloxyalkyl thiocyanates. J. Am. Chem. Soc. 1951, 73, 3159-3162.
37. 3-DTDA - A chelator-lipid that promotes stable binding of His-tagged proteins to membranes. Aust. J. Chem. 2006, 59, 302-306.
38. Bernatowicz, M.S.; Wu, Y.; Matsueda, G.R. 1H-Pyrazole-1-carboxamidine hydrochloride an attractive reagent for guanylation of amines and its application to peptide synthesis. J. Org. Chem. 1992, 57, 2497-2502.
39. v channels in SH-SY5Y human neuroblastoma cells. PLOS ONE 2013, 8, e59293.
40. McArthur, J.R.; Adams, D.J. RMIT University, Melbourne, Victoria, Australia. Personal Communication, 2015.
41. Alvarez, S.G.; Alvarez, M.T. A practical procedure for the synthesis of alkyl azides at ambient temperature in dimethyl sulfoxide in high purity and yield. Synthesis 1997, 1997, 413-414.
42. Evans, D.A.; Katz, J.L.; West, T.R. Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine. Tetrahedron Lett. 1998, 39, 2937-2940.
43. Bavin, P.M.G. The preparation of amines and hydrozo compounds using hydrazine and palladized charcoal. Can. J. Chem. 1958, 36, 238-241.
44. Maiti, D.; Buchwald, S.L. Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols. J. Am. Chem. Soc. 2009, 131, 17423-17429.
45. Pajouhesh, H.; Lenz, G. Medicinal chemical properties of successful central nervous system drugs. Neurotherapeutics 2005, 2, 541-553.