Calmidazolium (cation)

• CAT Number: I023980
• CAS Number: 95013-41-5
• Molecular Formula: C31H23Cl6N2O+
• Molecular Weight: 652.24
• Purity: 98%
• Synonyms: Calmidazolium (cation); R24571; R 24571; R-24571
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 1H-Imidazolium, 1-(bis(4-chlorophenyl)methyl)-3-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-
• InChI: InChI=1S/C31H23Cl6N2O/c32-23-6-1-20(2-7-23)31(21-3-8-24(33)9-4-21)39-14-13-38(19-39)17-30(27-12-11-26(35)16-29(27)37)40-18-22-5-10-25(34)15-28(22)36/h1-16,19,30-31H,17-18H2/q+1
• InChIKey: CTKNMSVWMRRCPW-UHFFFAOYSA-N
• SMILES: ClC1=CC=C(COC(C2=CC=C(Cl)C=C2Cl)C[N+]3=CN(C(C4=CC=C(Cl)C=C4)C5=CC=C(Cl)C=C5)C=C3)C(Cl)=C1

Calmidazolium (cation) is a powerful inhibitor of or red blood cell Ca -ATPase & Ca transport into inside-out red blood cell vesicles; an antagonist of calmodulin.

Reference

1: Budu A, Gomes MM, Melo PM, El Chamy Maluf S, Bagnaresi P, Azevedo MF, Carmona AK, Gazarini ML. Calmidazolium evokes high calcium fluctuations in Plasmodium falciparum. Cell Signal. 2016 Mar;28(3):125-135. doi: 10.1016/j.cellsig.2015.12.003. Epub 2015 Dec 10. PubMed PMID: 26689736.
2: Lee J, Kim MS, Kim MA, Jang YK. Calmidazolium chloride inhibits growth of murine embryonal carcinoma cells, a model of cancer stem-like cells. Toxicol In Vitro. 2016 Sep;35:86-92. doi: 10.1016/j.tiv.2016.05.015. Epub 2016 May 28. PubMed PMID: 27247146.
3: Cervetto C, Mazzotta MC, Frattaroli D, Alloisio S, Nobile M, Maura G, Marcoli M. Calmidazolium selectively inhibits exocytotic glutamate release evoked by P2X7 receptor activation. Neurochem Int. 2012 Jun;60(8):768-72. doi: 10.1016/j.neuint.2012.02.034. Epub 2012 Mar 6. PubMed PMID: 22417724.
4: Liao WC, Huang CC, Cheng HH, Wang JL, Lin KL, Cheng JS, Chai KL, Hsu PT, Tsai JY, Fang YC, Lu YC, Chang HT, Huang JK, Chou CT, Jan CR. Effect of calmidazolium on [Ca2+]i and viability in human hepatoma cells. Arch Toxicol. 2009 Jan;83(1):61-8. doi: 10.1007/s00204-008-0328-4. Epub 2008 Jul 11. PubMed PMID: 18629476.
5: Tseng LL, Huang CJ, Hsu SS, Chen JS, Cheng HH, Chang HT, Jiann BP, Jan CR. Effect of calmidazolium on Ca(+2) movement and proliferation in human osteosarcoma cells. Clin Exp Pharmacol Physiol. 2004 Oct;31(10):732-7. PubMed PMID: 15554916.
6: Anderson KW, Coll RJ, Murphy AJ. Inhibition of skeletal muscle sarcoplasmic reticulum CaATPase activity by calmidazolium. J Biol Chem. 1984 Sep 25;259(18):11487-90. PubMed PMID: 6236226.
7: Choi MS, Cooke BA. Calmidazolium is a potent stimulator of steroidogenesis via mechanisms not involving cyclic AMP, calcium or protein synthesis. Biochem J. 1992 Jan 1;281 ( Pt 1):291-6. PubMed PMID: 1310009; PubMed Central PMCID: PMC1130676.
8: Illiano S, Nagao T, Vanhoutte PM. Calmidazolium, a calmodulin inhibitor, inhibits endothelium-dependent relaxations resistant to nitro-L-arginine in the canine coronary artery. Br J Pharmacol. 1992 Oct;107(2):387-92. PubMed PMID: 1358391; PubMed Central PMCID: PMC1907889.
9: Jan CR, Tseng CJ. Calmidazolium-induced rises in cytosolic calcium concentrations in Madin Darby canine kidney cells. Toxicol Appl Pharmacol. 2000 Jan 15;162(2):142-50. PubMed PMID: 10637138.
10: Larsson C, Alling C. Calmidazolium inhibits muscarinic receptor-mediated PLC activation in SH-SY5Y cells. Neuroreport. 1995 Jun 19;6(9):1333-7. PubMed PMID: 7669998.
11: Grosman N. Effect of calmidazolium (R24571) on histamine release from isolated rat mast cells. Agents Actions. 1986 Mar;17(5-6):427-35. PubMed PMID: 2422900.
12: Lückhoff A, Bohnert M, Busse R. Effects of the calmodulin antagonists fendiline and calmidazolium on aggregation, secretion of ATP, and internal calcium in washed human platelets. Naunyn Schmiedebergs Arch Pharmacol. 1991 Jan;343(1):96-101. PubMed PMID: 2030746.
13: Gietzen K. Comparison of the calmodulin antagonists compound 48/80 and calmidazolium. Biochem J. 1983 Dec 15;216(3):611-6. PubMed PMID: 6141789; PubMed Central PMCID: PMC1152553.
14: Alvarez-Vega M, Baamonde A, Gutiérrez M, Hidalgo A, Menéndez L. Comparison of the effects of calmidazolium, morphine and bupivacaine on N-methyl-D-aspartate- and septide-induced nociceptive behaviour. Naunyn Schmiedebergs Arch Pharmacol. 1998 Dec;358(6):628-34. PubMed PMID: 9879721.
15: Burgoyne RD, Norman KM. Effect of calmidazolium and phorbol ester on catecholamine secretion from adrenal chromaffin cells. Biochim Biophys Acta. 1984 Sep 14;805(1):37-43. PubMed PMID: 6433992.
16: Schlatterer C, Schaloske R. Calmidazolium leads to an increase in the cytosolic Ca2+ concentration in Dictyostelium discoideum by induction of Ca2+ release from intracellular stores and influx of extracellular Ca2+. Biochem J. 1996 Jan 15;313 ( Pt 2):661-7. PubMed PMID: 8573107; PubMed Central PMCID: PMC1216958.
17: Reid DG, MacLachlan LK, Gajjar K, Voyle M, King RJ, England PJ. A proton nuclear magnetic resonance and molecular modeling study of calmidazolium (R24571) binding to calmodulin and skeletal muscle troponin C. J Biol Chem. 1990 Jun 15;265(17):9744-53. PubMed PMID: 2351670.
18: Harper JL, Daly JW. Effect of calmidazolium analogs on calcium influx in HL-60 cells. Biochem Pharmacol. 2000 Aug 1;60(3):317-24. PubMed PMID: 10856426.
19: Kindmark H, Köhler M, Gerwins P, Larsson O, Khan A, Wahl MA, Berggren PO. The imidazoline derivative calmidazolium inhibits voltage-gated Ca(2+)-channels and insulin release but has no effect on the phospholipase C system in insulin producing RINm5F-cells. Biosci Rep. 1994 Jun;14(3):145-58. PubMed PMID: 7833453.
20: Menéndez L, Baamonde A, Hidalgo A. Spinal effects of the calmodulin inhibitor calmidazolium on dorsal horn neurons in the rat. Acta Neurobiol Exp (Wars). 1999;59(1):31-5. PubMed PMID: 10230074.