Modulation of cellular Ca2+ handling by pyrazoles

British Journal of Pharmacology

Volumn 167, Issue 8, 2012, Pages 1712-1722

  Schleifer, H ^a   Doleschal, B ^b   Lichtenegger, M ^b   Oppenrieder, R ^b   Derler, I ^c   Frischauf, I ^c   Glasnov, T N ^d   Kappe, C O ^d   Romanin, C ^c   Groschner, K ^a  

^a MEDICAL UNIVERSITY OF GRAZ   (Austria)

^b UNIVERSITY OF GRAZ   (Austria)

^c JOHANNES KEPLER UNIVERSITY LINZ   (Austria)

^d UNIVERSITY OF GRAZ   (Austria)

Author keywords

mast cell degranulation; NFAT signalling; Orai; pyrazole Ca2+ channel blockers; receptor operated Ca2+ entry; store operated Ca2+ entry; transient receptor potential

Indexed keywords

CALCIUM; CALCIUM CHANNEL; CARBACHOL; FURA 2; MUSCARINIC RECEPTOR; PYRAZOLE DERIVATIVE; TRANSCRIPTION FACTOR NFAT; TRANSIENT RECEPTOR POTENTIAL CHANNEL; CALCIUM CHANNEL BLOCKING AGENT;

ARTICLE; CALCIUM TRANSPORT; CELL ACTIVATION; CELL FUNCTION; CELL TYPE; DRUG POTENCY; DRUG STRUCTURE; ELECTROPHYSIOLOGY; HUMAN; HUMAN CELL; IC 50; MAST CELL; MAST CELL DEGRANULATION; MEMBRANE CURRENT; PATCH CLAMP; PRIORITY JOURNAL; T LYMPHOCYTE ACTIVATION; ANIMAL; CELL STRAIN HEK293; DEGRANULATION; DRUG EFFECT; METABOLISM; PHYSIOLOGY; RAT; TUMOR CELL LINE;

ANIMALS; CALCIUM; CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS; CELL DEGRANULATION; CELL LINE, TUMOR; HEK293 CELLS; HUMANS; MAST CELLS; PYRAZOLES; RATS;

EID: 84870500198     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2012.02126.x     Document Type: Article

References (51)

1. Abramowitz J, Birnbaumer L, (2009). Physiology and pathophysiology of canonical transient receptor potential channels. FASEB J 23: 297-328.
2. Alexander SP, Mathie A, Peters JA, (2011). Guide to receptors and channels (GRAC), 5th edition. Br J Pharmacol 164 (Suppl. 1): S1-324.
3. Bergsmann J, Derler I, Muik M, Frischauf I, Fahrner M, Pollheimer P, et al,. (2011). Molecular determinants within N terminus of Orai3 protein that control channel activation and gating. J Biol Chem 286: 31565-31575.
4. Berridge MJ, Lipp P, Bootman MD, (2000). The versatility and universality of calcium signalling. Nat Rev Mol Cell Biol 1: 11-21.
5. Birsan T, Dambrin C, Marsh KC, Jacobsen W, Djuric SW, Mollison KW, et al,. (2004). Preliminary in vivo pharmacokinetic and pharmacodynamic evaluation of a novel calcineurin-independent inhibitor of NFAT. Transpl Int 17: 145-150.
6. Calloway N, Vig M, Kinet JP, Holowka D, Baird B, (2009). Molecular clustering of STIM1 with Orai1/CRACM1 at the plasma membrane depends dynamically on depletion of Ca2+ stores and on electrostatic interactions. Mol Biol Cell 20: 389-399.
7. Chen Y, Smith ML, Chiou GX, Ballaron S, Sheets MP, Gubbins E, et al,. (2002). TH1 and TH2 cytokine inhibition by 3,5-bis(trifluoromethyl)pyrazoles, a novel class of immunomodulators. Cell Immunol 220: 134-142.
8. Cheng KT, Liu X, Ong HL, Swaim W, Ambudkar IS, (2011). Local Ca(2)+ entry via Orai1 regulates plasma membrane recruitment of TRPC1 and controls cytosolic Ca(2)+ signals required for specific cell functions. PLoS Biol 9: e1001025.
9. DeHaven WI, Smyth JT, Boyles RR, Bird GS, Putney JW, Jr (2008). Complex actions of 2-aminoethyldiphenyl borate on store-operated calcium entry. J Biol Chem 283: 19265-19273.
10. Derler I, Fahrner M, Carugo O, Muik M, Bergsmann J, Schindl R, et al,. (2009). Increased hydrophobicity at the N terminus/membrane interface impairs gating of the severe combined immunodeficiency-related ORAI1 mutant. J Biol Chem 284: 15903-15915.
11. Di Capite J, Parekh AB, (2009). CRAC channels and Ca2+ signaling in mast cells. Immunol Rev 231: 45-58.
12. Djuric SW, BaMaung NY, Basha A, Liu H, Luly JR, Madar DJ, et al,. (2000). 3,5-Bis(trifluoromethyl)pyrazoles: a novel class of NFAT transcription factor regulator. J Med Chem 43: 2975-2981.
13. Glasnov TN, Groschner K, Kappe CO, (2009). High-speed microwave-assisted synthesis of the trifluoromethylpyrazol-derived canonical transient receptor potential (TRPC) channel inhibitor Pyr3. ChemMedChem 4: 1816-1818.
14. Graziani A, Poteser M, Heupel WM, Schleifer H, Krenn M, Drenckhahn D, et al,. (2010). Cell-cell contact formation governs Ca2+ signaling by TRPC4 in the vascular endothelium: evidence for a regulatory TRPC4-beta-catenin interaction. J Biol Chem 285: 4213-4223.
15. Harteneck C, Gollasch M, (2011). Pharmacological modulation of diacylglycerol-sensitive TRPC3/6/7 channels. Curr Pharm Biotechnol 12: 35-41.
16. He LP, Hewavitharana T, Soboloff J, Spassova MA, Gill DL, (2005). A functional link between store-operated and TRPC channels revealed by the 3,5-bis(trifluoromethyl)pyrazole derivative, BTP2. J Biol Chem 280: 10997-11006.
17. Hofmann T, Obukhov AG, Schaefer M, Harteneck C, Gudermann T, Schultz G, (1999). Direct activation of human TRPC6 and TRPC3 channels by diacylglycerol. Nature 397: 259-263.
18. Hoth M, Penner R, (1992). Depletion of intracellular calcium stores activates a calcium current in mast cells. Nature 355: 353-356.
19. Hoth M, Penner R, (1993). Calcium release-activated calcium current in rat mast cells. J Physiol 465: 359-386.
20. Ishikawa J, Ohga K, Yoshino T, Takezawa R, Ichikawa A, Kubota H, et al,. (2003). A pyrazole derivative, YM-58483, potently inhibits store-operated sustained Ca2+ influx and IL-2 production in T lymphocytes. J Immunol 170: 4441-4449.
21. Jardin I, Lopez JJ, Salido GM, Rosado JA, (2008). Orai1 mediates the interaction between STIM1 and hTRPC1 and regulates the mode of activation of hTRPC1-forming Ca2+ channels. J Biol Chem 283: 25296-25304.
22. Kar P, Nelson C, Parekh AB, (2011). Selective activation of the transcription factor NFAT1 by calcium microdomains near Ca2+ release-activated Ca2+ (CRAC) channels. J Biol Chem 286: 14795-14803.
23. Kim MS, Lee KP, Yang D, Shin DM, Abramowitz J, Kiyonaka S, et al,. (2011). Genetic and pharmacologic inhibition of the Ca2+ influx channel TRPC3 protects secretory epithelia from Ca2+-dependent toxicity. Gastroenterology 140: 2107-2115. 2115 e2101-2104.
24. Kiyonaka S, Kato K, Nishida M, Mio K, Numaga T, Sawaguchi Y, et al,. (2009). Selective and direct inhibition of TRPC3 channels underlies biological activities of a pyrazole compound. Proc Natl Acad Sci USA 106: 5400-5405.
25. Law M, Morales JL, Mottram LF, Iyer A, Peterson BR, August A, (2011). Structural requirements for the inhibition of calcium mobilization and mast cell activation by the pyrazole derivative BTP2. Int J Biochem Cell Biol 43: 1228-1239.
26. Lemonnier L, Trebak M, Putney JW, Jr (2008). Complex regulation of the TRPC3, 6 and 7 channel subfamily by diacylglycerol and phosphatidylinositol-4,5- bisphosphate. Cell Calcium 43: 506-514.
27. Liao Y, Erxleben C, Yildirim E, Abramowitz J, Armstrong DL, Birnbaumer L, (2007). Orai proteins interact with TRPC channels and confer responsiveness to store depletion. Proc Natl Acad Sci USA 104: 4682-4687.
28. Ma HT, Peng Z, Hiragun T, Iwaki S, Gilfillan AM, Beaven MA, (2008). Canonical transient receptor potential 5 channel in conjunction with Orai1 and STIM1 allows Sr2+ entry, optimal influx of Ca2+, and degranulation in a rat mast cell line. J Immunol 180: 2233-2239.
29. Muik M, Frischauf I, Derler I, Fahrner M, Bergsmann J, Eder P, et al,. (2008). Dynamic coupling of the putative coiled-coil domain of ORAI1 with STIM1 mediates ORAI1 channel activation. J Biol Chem 283: 8014-8022.
30. Mundell SJ, Benovic JL, (2000). Selective regulation of endogenous G protein-coupled receptors by arrestins in HEK293 cells. J Biol Chem 275: 12900-12908.
31. Ng SW, di Capite J, Singaravelu K, Parekh AB, (2008). Sustained activation of the tyrosine kinase Syk by antigen in mast cells requires local Ca2+ influx through Ca2+ release-activated Ca2+ channels. J Biol Chem 283: 31348-31355.
32. Nilius B, Owsianik G, Voets T, Peters JA, (2007). Transient receptor potential cation channels in disease. Physiol Rev 87: 165-217.
33. Obermayer D, Glasnov TN, Kappe CO, (2011). Microwave-assisted and continuous flow multistep synthesis of 4-(pyrazol-1-yl)carboxanilides. J Org Chem 76: 6657-6669.
34. Pedersen SF, Owsianik G, Nilius B, (2005). TRP channels: an overview. Cell Calcium 38: 233-252.
35. Poteser M, Schleifer H, Lichtenegger M, Schernthaner M, Stockner T, Kappe CO, et al,. (2011). PKC-dependent coupling of calcium permeation through transient receptor potential canonical 3 (TRPC3) to calcineurin signaling in HL-1 myocytes. Proc Natl Acad Sci USA 108: 10556-10561.
36. Prakriya M, Feske S, Gwack Y, Srikanth S, Rao A, Hogan PG, (2006). Orai1 is an essential pore subunit of the CRAC channel. Nature 443: 230-233.
37. Putney JW, Jr (2004). The enigmatic TRPCs: multifunctional cation channels. Trends Cell Biol 14: 282-286.
38. Salmon MD, Ahluwalia J, (2010). Discrimination between receptor- and store-operated Ca(2+) influx in human neutrophils. Cell Immunol 265: 1-5.
39. Salmon MD, Ahluwalia J, (2011). Pharmacology of receptor operated calcium entry in human neutrophils. Int Immunopharmacol 11: 145-148.
40. Schindl R, Frischauf I, Kahr H, Fritsch R, Krenn M, Derndl A, et al,. (2008). The first ankyrin-like repeat is the minimum indispensable key structure for functional assembly of homo- and heteromeric TRPC4/TRPC5 channels. Cell Calcium 43: 260-269.
41. Shirakawa H, Sakimoto S, Nakao K, Sugishita A, Konno M, Iida S, et al,. (2010). Transient receptor potential canonical 3 (TRPC3) mediates thrombin-induced astrocyte activation and upregulates its own expression in cortical astrocytes. J Neurosci 30: 13116-13129.
42. Sinkins WG, Goel M, Estacion M, Schilling WP, (2004). Association of immunophilins with mammalian TRPC channels. J Biol Chem 279: 34521-34529.
43. Sweeney ZK, Minatti A, Button DC, Patrick S, (2009). Small-molecule inhibitors of store-operated calcium entry. ChemMedChem 4: 706-718.
44. Thyagarajan B, Poteser M, Romanin C, Kahr H, Zhu MX, Groschner K, (2001). Expression of Trp3 determines sensitivity of capacitative Ca2+ entry to nitric oxide and mitochondrial Ca2+ handling: evidence for a role of Trp3 as a subunit of capacitative Ca2+ entry channels. J Biol Chem 276: 48149-48158.
45. Trebak M, Bird GS, McKay RR, Putney JW, Jr (2002). Comparison of human TRPC3 channels in receptor-activated and store-operated modes. Differential sensitivity to channel blockers suggests fundamental differences in channel composition. J Biol Chem 277: 21617-21623.
46. Trevillyan JM, Chiou XG, Chen YW, Ballaron SJ, Sheets MP, Smith ML, et al,. (2001). Potent inhibition of NFAT activation and T cell cytokine production by novel low molecular weight pyrazole compounds. J Biol Chem 276: 48118-48126.
47. Woodard GE, Lopez JJ, Jardin I, Salido GM, Rosado JA, (2010). TRPC3 regulates agonist-stimulated Ca2+ mobilization by mediating the interaction between type I inositol 1,4,5-trisphosphate receptor, RACK1, and Orai1. J Biol Chem 285: 8045-8053.
48. Yonetoku Y, Kubota H, Miyazaki Y, Okamoto Y, Funatsu M, Yoshimura-Ishikawa N, et al,. (2008). Novel potent and selective Ca2+ release-activated Ca2+ (CRAC) channel inhibitors. Part 3: synthesis and CRAC channel inhibitory activity of 4'-[(trifluoromethyl)pyrazol-1-yl]carboxanilides. Bioorg Med Chem 16: 9457-9466.
49. Yuan JP, Kim MS, Zeng W, Shin DM, Huang G, Worley PF, et al,. (2009). TRPC channels as STIM1-regulated SOCs. Channels (Austin) 3: 221-225.
50. Zhang SL, Yu Y, Roos J, Kozak JA, Deerinck TJ, Ellisman MH, et al,. (2005). STIM1 is a Ca2+ sensor that activates CRAC channels and migrates from the Ca2+ store to the plasma membrane. Nature 437: 902-905.
51. Zitt C, Strauss B, Schwarz EC, Spaeth N, Rast G, Hatzelmann A, et al,. (2004). Potent inhibition of Ca2+ release-activated Ca2+ channels and T-lymphocyte activation by the pyrazole derivative BTP2. J Biol Chem 279: 12427-12437.