Synthesis and characterisation of NS13558: A new important tool for addressing KCa1.1 channel function ex vivo

Naunyn-Schmiedeberg's Archives of Pharmacology

Volumn 381, Issue 3, 2010, Pages 271-283

  Bentzen, Bo Hjorth ^a   Andersen, Rune Wederkinck ^b   Olesen, Søren Peter ^a   Grunnet, Morten ^b   Nardi, Antonio ^b  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b NEUROSEARCH A S   (Denmark)

Author keywords

BK openers; Cardioprotection; Inactive analogue; Ischemia; KCa1.1 channel activators

Indexed keywords

1 (3,5 BIS TRIFLUOROMETHYL PHENYL) 3 [4 BROMO 2 (1H TETRAZOL 5 YL) PHENYL] THIOUREA; 1 (3,5 BIS TRIFLUOROMETHYL PHENYL) 3 [4 BROMO 2 (2 METHYL 2H TETRAZOL 5 YL) PHENYL] THIOUREA; CALCIUM ACTIVATED POTASSIUM CHANNEL; COMPLEMENTARY DNA; DRUG DERIVATIVE; NS 11021; NS 13558; POTASSIUM CHANNEL STIMULATING AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL CULTURE; CELL ISOLATION; CELL STRAIN HEK293; CONTROLLED STUDY; CRYSTALLOGRAPHY; DRUG ACTIVATION; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHYSIOLOGY; HEART INFARCTION SIZE; HEART MUSCLE CELL; HEART PERFUSION; HEART PROTECTION; IN VITRO STUDY; MALE; MELTING POINT; MITOCHONDRIAL MEMBRANE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SPRAGUE DAWLEY RAT; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; VOLTAGE CLAMP;

ACTION POTENTIALS; ANIMALS; CARDIOTONIC AGENTS; CELL LINE; HUMANS; LARGE-CONDUCTANCE CALCIUM-ACTIVATED POTASSIUM CHANNEL ALPHA SUBUNITS; MALE; MOLECULAR STRUCTURE; MYOCARDIAL INFARCTION; MYOCARDIAL REPERFUSION INJURY; OOCYTES; PATCH-CLAMP TECHNIQUES; PERFUSION; RATS; RATS, SPRAGUE-DAWLEY; TETRAZOLES; THIOUREA; TRANSFECTION; XENOPUS LAEVIS;

EID: 77954085381     PISSN: 00281298     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00210-009-0456-2     Document Type: Article

References (37)

1. F Andreini G Biagi I Giorgi O Livi V Scartoni 1989 Modification of the 1, 2, 3-triazole ring present in an effective in vitro inhibitor of the prostaglandin synthesis Farmaco 44 831 841 1:CAS:528:DyaK3MXitlyktQ%3D%3D 2513819
2. BH Bentzen A Nardi K Calloe LS Madsen SP Olesen M Grunnet 2007 The small molecule NS11021 is a potent and specific activator of Ca2+-activated big-conductance K+ channels Mol Pharmacol 72 1033 1044 10.1124/mol.107.038331 1:CAS:528:DC%2BD2sXhtFaiu7zK 17636045 (Pubitemid 47481426)
3. Bentzen BH, Osadchii O, Jespersen T, Hansen RS, Olesen SP, Grunnet M (2008) Activation of big conductance Ca(2+)-activated K(+) channels (BK) protects the heart against ischemia-reperfusion injury. Pflugers Arch
4. DV Cancherini BB Queliconi AJ Kowaltowski 2007 Pharmacological and physiological stimuli do not promote Ca(2+)-sensitive K+ channel activity in isolated heart mitochondria Cardiovasc Res 73 720 728 10.1016/j.cardiores.2006. 11.035 1:CAS:528:DC%2BD2sXhvVyms7Y%3D 17208207 (Pubitemid 46227347)
5. CM Cao Q Xia Q Gao M Chen TM Wong 2005 Calcium-activated potassium channel triggers cardioprotection of ischemic preconditioning J Pharmacol Exp Ther 312 644 650 10.1124/jpet.104.074476 1:CAS:528:DC%2BD2MXhsVCntr4%3D 15345753 (Pubitemid 40189562)
6. TJ De Boer HJ Backer 1963 Diazomethane Org Synth 36 16 19
7. G Debska A Kicinska J Dobrucki B Dworakowska E Nurowska J Skalska K Dolowy A Szewczyk 2003 Large-conductance K+ channel openers NS1619 and NS004 as inhibitors of mitochondrial function in glioma cells Biochem Pharmacol 65 1827 1834 10.1016/S0006-2952(03)00180-1 1:CAS:528:DC%2BD3sXktVOrs7k%3D 12781334 (Pubitemid 36629507)
8. RM Douglas JC Lai S Bian L Cummins E Moczydlowski GG Haddad 2006 The calcium-sensitive large-conductance potassium channel (BK/MAXI K) is present in the inner mitochondrial membrane of rat brain Neuroscience 139 1249 1261 10.1016/j.neuroscience.2006.01.061 1:CAS:528:DC%2BD28XktVGhurk%3D 16567053
9. G Edwards A Niederste-Hollenberg J Schneider T Noack AH Weston 1994 Ion channel modulation by NS 1619, the putative BKCa channel opener, in vascular smooth muscle Br J Pharmacol 113 1538 1547 1:CAS:528:DyaK2MXisFajurs%3D 7534190
10. M Grunnet BS Jensen SP Olesen DA Klaerke 2001 Apamin interacts with all subtypes of cloned small-conductance Ca2+-activated K+ channels Pflugers Arch 441 544 550 10.1007/s004240000447 1:CAS:528:DC%2BD3MXlt1Ogtg%3D%3D 11212219 (Pubitemid 32128151)
11. AP Halestrap SJ Clarke I Khaliulin 2007 The role of mitochondria in protection of the heart by preconditioning Biochim Biophys Acta 1767 1007 1031 10.1016/j.bbabio.2007.05.008 1:CAS:528:DC%2BD2sXot1yktb8%3D 17631856 (Pubitemid 47101788)
12. RS Hansen TG Diness T Christ J Demnitz U Ravens SP Olesen M Grunnet 2006 Activation of human ether-a-go-go-related gene potassium channels by the diphenylurea 1,3-bis-(2-hydroxy-5-trifluoromethyl-phenyl)-urea (NS1643) Mol Pharmacol 69 266 277 1:CAS:528:DC%2BD28XktlWmsg%3D%3D 16219910
13. A Heinen AK Camara M Aldakkak SS Rhodes ML Riess DF Stowe 2007 Mitochondrial Ca2+-induced K+ influx increases respiration and enhances ROS production while maintaining membrane potential Am J Physiol Cell Physiol 292 C148 C156 10.1152/ajpcell.00215.2006 1:CAS:528:DC%2BD2sXisFCrtbs%3D 16870831 (Pubitemid 46115128)
14. GF Holland JN Pereira 1967 Heterocyclic tetrazoles, a new class of lipolysis inhibitors J Med Chem 10 149 154 10.1021/jm00314a004 1:CAS:528:DyaF2sXosFOgtQ%3D%3D 6034054
15. M Holland PD Langton NB Standen JP Boyle 1996 Effects of the BKCa channel activator, NS1619, on rat cerebral artery smooth muscle Br J Pharmacol 117 119 129 1:CAS:528:DyaK28Xlt1CmtQ%3D%3D 8825352
16. T Jespersen M Grunnet K Angelo DA Klaerke SP Olesen 2002 Dual-function vector for protein expression in both mammalian cells and Xenopus laevis oocytes Biotechniques 32 536 540 1:CAS:528:DC%2BD38XitFCns7Y%3D 11911656
17. CL Longland JL Dyer F Michelangeli 2000 The mycotoxin paxilline inhibits the cerebellar inositol 1,4,5-trisphosphate receptor Eur J Pharmacol 408 219 225 10.1016/S0014-2999(00)00775-5 1:CAS:528:DC%2BD3cXot1ygsLc%3D 11090637
18. A Nardi S-P Olesen 2008 Curr Med Chem 15 1126 1146 10.2174/ 092986708784221412 1:CAS:528:DC%2BD1cXnsVyiu78%3D 18473808 (Pubitemid 352002981)
19. Nardi A, Demnitz D, Grunnet M, Christophersen P, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008a) Preparation of novel biphenyl thiourea derivatives useful as potassium channel modulators. PCT Int Appl WO/2008/074756
20. Nardi A, Christensen JK, Christophersen P, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008b) Preparation of novel aromatic heterocyclic carboxylic acid amide derivatives as potassium channel modulators. PCT Int Appl WO/2008/138917
21. Nardi A, Demnitz D, Grunnet M, Christophersen P, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008c) Preparation of novel benzamidine derivatives as potassium channel modulators. PCT Int Appl WO/2008/135591
22. Nardi A, Demnitz D, Grunnet M, Christophersen P, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008d) Preparation of β-keto-amide derivatives useful as ion channel modulators. PCT Int Appl WO/2008/135448
23. Nardi A, Grunnet M, Christophersen P, Demnitz J, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008e) Preparation of acetamide derivatives as potassium channel modulators. PCT Int Appl WO/2008/135447
24. Nardi A, Grunnet M, Christophersen P, Demnitz J, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008f) Preparation of diaryltriazole derivatives for use as potassium channel modulators. PCT Int Appl WO/2008/087178
25. Nardi A, Demnitz D, Grunnet M, Christophersen P, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008g) Preparation of novel semicarbazide and carbonylhydrazide derivatives useful as potassium channel modulators. PCT Int Appl WO/2008/087177
26. Nardi A, Grunnet M, Demnitz J, Jensen TD, Christophersen P, Jones DS, Nielsen EO, Stroebaek D, Madsen LS (2008h) Preparation of novel cinnamic amide derivatives useful as ion channel modulators. PCT Int Appl WO/2008/074755
27. Nardi A, Christensen JK, Jones DS (2009) Preparation of novel pyrazole derivatives useful as potassium channel modulators. PCT Int Appl WO/2009/003921
28. B O'Rourke 2007 Mitochondrial ion channels Annu Rev Physiol 69 19 49 10.1146/annurev.physiol.69.031905.163804 17059356 (Pubitemid 46457634)
29. Ohya S, Kuwata Y, Sakamoto K, Muraki K, Imaizumi Y (2005) Cardioprotective effects of estradiol include the activation of large-conductance Ca(2+)-activated K(+) channels in cardiac mitochondria. Am J Physiol Heart Circ Physiol 289:1635-1642
30. SP Olesen E Munch P Moldt J Drejer 1994 Selective activation of Ca(2+)-dependent K+ channels by novel benzimidazolone Eur J Pharmacol 251 53 59 10.1016/0014-2999(94)90442-1 1:CAS:528:DyaK2cXhvValtbY%3D 8137869
31. WS Park SH Kang YK Son N Kim JH Ko HK Kim EA Ko CD Kim J Han 2007 The mitochondrial Ca2+-activated K+ channel activator, NS 1619 inhibits l-type Ca2+ channels in rat ventricular myocytes Biochem Biophys Res Commun 362 31 36 10.1016/j.bbrc.2007.07.057 1:CAS:528:DC%2BD2sXpsFKks7c%3D 17698036 (Pubitemid 47304404)
32. K Sakamoto T Nonomura S Ohya K Muraki T Ohwada Y Imaizumi 2006 Molecular mechanisms for large conductance Ca2+-activated K+ channel activation by a novel opener, 12,14-dichlorodehydroabietic acid J Pharmacol Exp Ther 316 144 153 10.1124/jpet.105.093856 1:CAS:528:DC%2BD28XhslertQ%3D%3D 16195419 (Pubitemid 41832591)
33. K Sakamoto S Ohya K Muraki Y Imaizumi 2008 A novel opener of large-conductance Ca2+-activated K+ (BK) channel reduces ischemic injury in rat cardiac myocytes by activating mitochondrial K(Ca) channel J Pharmacol Sci 108 135 139 10.1254/jphs.08150SC 1:CAS:528:DC%2BD1cXht1amtrzI 18758135
34. SN Saleh JE Angermann WR Sones N Leblanc IA Greenwood 2007 Stimulation of Ca2+-gated Cl-currents by the calcium-dependent K+ channel modulators NS1619 [1, 3-dihydro-1-[2-hydroxy-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2 H-benzimidazol-2-one] and isopimaric acid J Pharmacol Exp Ther 321 1075 1084 10.1124/jpet.106.118786 1:CAS:528:DC%2BD2sXmsFeqs7s%3D 17347326 (Pubitemid 46762684)
35. D Siemen C Loupatatzis J Borecky E Gulbins F Lang 1999 Ca2+-activated K channel of the BK-type in the inner mitochondrial membrane of a human glioma cell line Biochem Biophys Res Commun 257 549 554 10.1006/bbrc.1999.0496 1:CAS:528:DyaK1MXit1yktrs%3D 10198249 (Pubitemid 29301480)
36. X Wang C Yin L Xi RC Kukreja 2004 Opening of Ca2+-activated K+ channels triggers early and delayed preconditioning against I/R injury independent of NOS in mice Am J Physiol Heart Circ Physiol 287 H2070 H2077 10.1152/ajpheart.00431. 2004 1:CAS:528:DC%2BD2cXhtVaqtr3P 15217801 (Pubitemid 39430745)
37. W Xu Y Liu S Wang T McDonald JE Van Eyk A Sidor B O'Rourke 2002 Cytoprotective role of Ca2+-activated K+ channels in the cardiac inner mitochondrial membrane Science 298 1029 1033 10.1126/science.1074360 1:CAS:528:DC%2BD38Xot12rs70%3D 12411707 (Pubitemid 35247311)