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Home > Imidazoles > 57265-65-3
57265-65-3 | CALMIDAZOLIUM CHLORIDE
CAS No: 57265-65-3 Catalog No: AG00EDRN MDL No:
Product Description
Catalog Number:
AG00EDRN
Chemical Name:
CALMIDAZOLIUM CHLORIDE
CAS Number:
57265-65-3
Molecular Formula:
C31H23Cl7N2O
Molecular Weight:
687.6981
IUPAC Name:
1-[bis(4-chlorophenyl)methyl]-3-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazol-3-ium;chloride
InChI:
InChI=1S/C31H23Cl6N2O.ClH/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;1H/q+1;/p-1
InChI Key:
YGEIMSMISRCBFF-UHFFFAOYSA-M
SMILES:
Clc1ccc(cc1)C(n1cc[n+](c1)CC(c1ccc(cc1Cl)Cl)OCc1ccc(cc1Cl)Cl)c1ccc(cc1)Cl.[Cl-]
Properties
Complexity:
742
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
685.96g/mol
Formal Charge:
0
Heavy Atom Count:
41
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
687.688g/mol
Monoisotopic Mass:
683.963g/mol
Rotatable Bond Count:
9
Topological Polar Surface Area:
18A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Calmidazolium chloride inhibits growth of murine embryonal carcinoma cells, a model of cancer stem-like cells. | Toxicology in vitro : an international journal published in association with BIBRA 20160901 |
| Regulation of NKG2D-ligand cell surface expression by intracellular calcium after HDAC-inhibitor treatment. | Molecular immunology 20130301 |
| Calmidazolium selectively inhibits exocytotic glutamate release evoked by P2X7 receptor activation. | Neurochemistry international 20120601 |
| Biochemical characterization of a recombinant Swainsona canescens calcium-dependent protein kinase (ScCPK1). | Plant physiology and biochemistry : PPB 20120501 |
| Interactions of Bordetella pertussis adenylyl cyclase toxin CyaA with calmodulin mutants and calmodulin antagonists: comparison with membranous adenylyl cyclase I. | Biochemical pharmacology 20120401 |
| A comprehensive strategy to discover inhibitors of the translesion synthesis DNA polymerase κ. | PloS one 20120101 |
| LuxR dependent quorum sensing inhibition by N,N'-disubstituted imidazolium salts. | Bioorganic & medicinal chemistry 20110815 |
| Glutamate-induced calcium signals stimulate CO production in piglet astrocytes. | American journal of physiology. Heart and circulatory physiology 20110801 |
| Paradoxical facilitation of exocytosis by inhibition of L-type calcium channels of bovine chromaffin cells. | Biochemical and biophysical research communications 20110701 |
| Secretoneurin facilitates endothelium-dependent relaxations in porcine coronary arteries. | American journal of physiology. Heart and circulatory physiology 20110401 |
| Calmodulin and calmodulin-dependent protein kinase II inhibit hormone secretion in human parathyroid adenoma. | The Journal of endocrinology 20110101 |
| Mesodermal progenitor cells (MPCs) differentiate into mesenchymal stromal cells (MSCs) by activation of Wnt5/calmodulin signalling pathway. | PloS one 20110101 |
| Permissive role of sphingosine on calcium-dependent endocytosis in chromaffin cells. | Pflugers Archiv : European journal of physiology 20101001 |
| Calmodulin-dependent nuclear import of HMG-box family nuclear factors: importance of the role of SRY in sex reversal. | The Biochemical journal 20100815 |
| Possible participation of calmodulin in the decondensation of nuclei isolated from guinea pig spermatozoa. | Zygote (Cambridge, England) 20100801 |
| LuxR-dependent quorum sensing: computer aided discovery of new inhibitors structurally unrelated to N-acylhomoserine lactones. | Bioorganic & medicinal chemistry letters 20100801 |
| Mechanism of inhibition of acetylcholine secretion in newly formed mouse synapses involving Ca2+-dependent kinases and voltage-gated K+-channels. | Bulletin of experimental biology and medicine 20100801 |
| Nicotinamide adenine dinucleotide phosphate reduced oxidase 5 (Nox5) regulation by angiotensin II and endothelin-1 is mediated via calcium/calmodulin-dependent, rac-1-independent pathways in human endothelial cells. | Circulation research 20100430 |
| PTTH-stimulated ERK phosphorylation in prothoracic glands of the silkworm, Bombyx mori: role of Ca(2+)/calmodulin and receptor tyrosine kinase. | Journal of insect physiology 20100101 |
| Pyk2 uncouples metabotropic glutamate receptor G protein signaling but facilitates ERK1/2 activation. | Molecular brain 20100101 |
| Regulation of Na+/H+ exchanger isoform 1 (NHE1) by calmodulin-binding sites: role of angiotensin II. | Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20100101 |
| Inhibition of nitric oxide-activated guanylyl cyclase by calmodulin antagonists. | British journal of pharmacology 20091101 |
| Caffeine inhibits nonselective cationic currents in interstitial cells of Cajal from the murine jejunum. | American journal of physiology. Cell physiology 20091001 |
| Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. | Nature chemical biology 20091001 |
| Regulation of store-operated Ca2+ entry in pulmonary artery smooth muscle cells. | Cell calcium 20090801 |
| Determining time of death: temperature-dependent postmortem changes in calcineurin A, MARCKS, CaMKII, and protein phosphatase 2A in mouse. | International journal of legal medicine 20090701 |
| Behavioral adaptation in C. elegans produced by antipsychotic drugs requires serotonin and is associated with calcium signaling and calcineurin inhibition. | Neuroscience research 20090701 |
| Pituitary adenylate cyclase-activating polypeptide induces somatolactin release from cultured goldfish pituitary cells. | Peptides 20090701 |
| Calcium fingerprints induced by calmodulin interactors in eukaryotic cells. | Biochimica et biophysica acta 20090601 |
| Computational modelling suggests dynamic interactions between Ca2+, IP3 and G protein-coupled modules are key to robust Dictyostelium aggregation. | Molecular bioSystems 20090601 |
| Activation of ROS/NF-kappaB and Ca2+/CaM kinase II are necessary for VCAM-1 induction in IL-1beta-treated human tracheal smooth muscle cells. | Toxicology and applied pharmacology 20090515 |
| A role for calcium-calmodulin in regulating nitric oxide production during skeletal muscle satellite cell activation. | American journal of physiology. Cell physiology 20090401 |
| Calmodulin and guanylyl cyclase inhibitors block the in vivo expression of gLTP in sympathetic ganglia from chronically stressed rats. | Neuroscience research 20090201 |
| Effect of calmidazolium on [Ca2+]i and viability in human hepatoma cells. | Archives of toxicology 20090101 |
| Isometric contraction increases endothelial nitric oxide synthase activity via a calmodulin antagonist-sensitive pathway in rat aorta. | Vascular pharmacology 20090101 |
| Short-term synaptic depression and recovery at the mature mammalian endbulb of Held synapse in mice. | Journal of neurophysiology 20080901 |
| [Calmodulin antagonists are involved in mouse sperm capacitation]. | Zhonghua nan ke xue = National journal of andrology 20080301 |
| Calcium-independent phospholipase A2 mediates store-operated calcium entry in rat cerebellar granule cells. | Cerebellum (London, England) 20080101 |
| Intracellular calcium regulation of connexin43. | American journal of physiology. Cell physiology 20071201 |
| Calcium absorption by Cav1.3 induces terminal web myosin II phosphorylation and apical GLUT2 insertion in rat intestine. | The Journal of physiology 20070415 |
| Interaction between store-operated and arachidonate-activated calcium entry. | Cell calcium 20070101 |
| Differential modulation of 7-ketocholesterol toxicity against PC12 cells by calmodulin antagonists and Ca2+ channel blockers. | Neurochemical research 20070101 |
| Calcium-calmodulin mediates house dust mite-induced ERK activation and IL-8 production in human respiratory epithelial cells. | Respiration; international review of thoracic diseases 20070101 |
| Anti-calmodulins and tricyclic adjuvants in pain therapy block the TRPV1 channel. | PloS one 20070101 |
| Signalling pathways involved in hypertonicity- and acidification-induced activation of Na+/H+ exchange in trout hepatocytes. | The Journal of experimental biology 20060801 |
| Modulation of human erythrocyte Ca2+-ATPase activity by glycerol: the role of calmodulin. | Biochemistry. Biokhimiia 20060801 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Protection of TRPC7 cation channels from calcium inhibition by closely associated SERCA pumps. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20060301 |
| Effects of streptozotocin-induced diabetes and insulin on calcium responsiveness of the rat vas deferens. | Life sciences 20060202 |
| Modulation by brain natriuretic peptide of GABA receptors on rat retinal ON-type bipolar cells. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20060111 |
| High glucose-induced apoptosis through store-operated calcium entry and calcineurin in human umbilical vein endothelial cells. | Cell calcium 20060101 |
| Neural tube closure depends on nitric oxide synthase activity. | Journal of neurochemistry 20060101 |
| Differential effect of calmodulin antagonists on MG132-induced mitochondrial dysfunction and cell death in PC12 cells. | Brain research bulletin 20051015 |
| Nitric oxide increases carbon monoxide production by piglet cerebral microvessels. | American journal of physiology. Heart and circulatory physiology 20051001 |
| Calcium and protein phosphatase 1/2A attenuate N-methyl-D-aspartate receptor activity in the anoxic turtle cortex. | Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20050901 |
| High-affinity peripheral benzodiazepine receptor ligand, PK11195, regulates protein phosphorylation in rat brain mitochondria under control of Ca(2+). | Journal of neurochemistry 20050801 |
| Mechanism of riboflavin uptake by cultured human retinal pigment epithelial ARPE-19 cells: possible regulation by an intracellular Ca2+-calmodulin-mediated pathway. | The Journal of physiology 20050715 |
| The decrease in the presynaptic calcium current is a major cause of short-term depression at a calyx-type synapse. | Neuron 20050519 |
| Altered transcriptional regulators in response to serum in immortalized lymphocytes from Alzheimer's disease patients. | Neurobiology of aging 20050501 |
| Biotin uptake by human proximal tubular epithelial cells: cellular and molecular aspects. | American journal of physiology. Renal physiology 20050401 |
| Virtual screening of novel noncovalent inhibitors for SARS-CoV 3C-like proteinase. | Journal of chemical information and modeling 20050101 |
| [The calmodulin inhibitor R24571 induces a short-term Ca2+ entry and a pulse-like secretion of ATP in Ehrlich ascites tumor cells]. | Biofizika 20050101 |
| Nicotine enhancement of dopamine release by a calcium-dependent increase in the size of the readily releasable pool of synaptic vesicles. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20041215 |
| Effect of calmidazolium on Ca(+2) movement and proliferation in human osteosarcoma cells. | Clinical and experimental pharmacology & physiology 20041001 |
| Calmidazolium and arachidonate activate a calcium entry pathway that is distinct from store-operated calcium influx in HeLa cells. | The Biochemical journal 20040801 |
| Fast Ca(2+)-dependent inactivation of the store-operated Ca2+ current (ISOC) in liver cells: a role for calmodulin. | The Journal of physiology 20040701 |
| Effect of serotonin on ciliary beating and intracellular calcium concentration in identified populations of embryonic ciliary cells. | The Journal of experimental biology 20040301 |
| Mitochondrial calcium uptake stimulates nitric oxide production in mitochondria of bovine vascular endothelial cells. | American journal of physiology. Cell physiology 20040201 |
| A novel mechanism for the store-operated calcium influx pathway. | Nature cell biology 20040201 |
| A SOX9 defect of calmodulin-dependent nuclear import in campomelic dysplasia/autosomal sex reversal. | The Journal of biological chemistry 20030905 |
| Physiological Ca2+ level and Ca2+-induced Permeability Transition Pore control protein phosphorylation in rat brain mitochondria. | Cell calcium 20030901 |
| Functional and genetic characterization of calmodulin from the dimorphic and pathogenic fungus Paracoccidioides brasiliensis. | Fungal genetics and biology : FG & B 20030801 |
| Ca2+/calmodulin-dependent modulation of cell cycle elements pRb and p27kip1 involved in the enhanced proliferation of lymphoblasts from patients with Alzheimer dementia. | Neurobiology of disease 20030801 |
| Calmodulin antagonists differentially affect capacitation-associated protein tyrosine phosphorylation of mouse sperm components. | Journal of cell science 20030515 |
| Structure-function relationships of AE2 regulation by Ca(i)(2+)-sensitive stimulators NH(4+) and hypertonicity. | American journal of physiology. Cell physiology 20030501 |
| Ca2+/calmodulin-dependent protein kinases II and IV both promote survival but differ in their effects on axon growth in spiral ganglion neurons. | Journal of neuroscience research 20030415 |
| Small ligands modulating the activity of mammalian adenylyl cyclases: a novel mode of inhibition by calmidazolium. | Molecular pharmacology 20030301 |
| Regulation of glutamatergic neurotransmission in the striatum by presynaptic adenylyl cyclase-dependent processes. | Neurochemistry international 20030101 |
| Cyclic AMP-mediated regulation of striatal glutamate release: interactions of presynaptic ligand- and voltage-gated ion channels and G-protein-coupled receptors. | Neurochemistry international 20030101 |
| Effects of subchronic and chronic melatonin treatment on somatostatin binding and its effects on adenylyl cyclase activity in the rat frontoparietal cortex. | Journal of pineal research 20021101 |
| Calmodulin-dependent kinase I regulates adrenal cell expression of aldosterone synthase. | Endocrinology 20020901 |
| Regulation of apical transporter of L-DOPA in human intestinal Caco-2 cells. | Acta physiologica Scandinavica 20020601 |
| A Ca(2+)-inhibited non-selective cation conductance contributes to pacemaker currents in mouse interstitial cell of Cajal. | The Journal of physiology 20020501 |
| Migration of primary cultured rabbit gastric epithelial cells requires intact protein kinase C and Ca2+/calmodulin activity. | Digestive diseases and sciences 20020501 |
| Effect of calmodulin antagonists on phospholipase D activity in SH-SY5Y cells. | Neurochemistry international 20020301 |
| Mechanism and regulation of vitamin B(6) uptake by renal tubular epithelia: studies with cultured OK cells. | American journal of physiology. Renal physiology 20020301 |
| Amplifying effect of the selective calmodulin antagonist, calmidazolium, on the potency of nifedipine to inhibit alpha 1D-adrenoceptor-mediated contraction in the rat aorta. | Proceedings of the Western Pharmacology Society 20020101 |
| Mitochondrial nitric oxide synthase is constitutively active and is functionally upregulated in hypoxia. | Free radical biology & medicine 20011215 |
| Activation of plasma membrane H+-ATPase by ammonium ions in Aspergillus niger. | Applied microbiology and biotechnology 20011001 |
| Detection of calmodulin-binding proteins and calmodulin-dependent phosphorylation linked to calmodulin-dependent chemotaxis to folic and cAMP in Dictyostelium. | Cellular signalling 20010801 |
| Calcium and pituitary adenylate cyclase-activating polypeptide induced expression of circadian clock gene mPer1 in the mouse cerebellar granule cell culture. | Journal of neurochemistry 20010801 |
| Phospholipase D activation by norepinephrine is mediated by 12(s)-, 15(s)-, and 20-hydroxyeicosatetraenoic acids generated by stimulation of cytosolic phospholipase a2. tyrosine phosphorylation of phospholipase d2 in response to norepinephrine. | The Journal of biological chemistry 20010511 |
| Involvement of calmodulin in glucagon-like peptide 1(7-36) amide-induced inhibition of the ATP-sensitive K+ channel in mouse pancreatic beta-cells. | Experimental physiology 20010501 |
| N-methyl-D-aspartate receptor-mediated mitochondrial Ca(2+) overload in acute excitotoxic motor neuron death: a mechanism distinct from chronic neurotoxicity after Ca(2+) influx. | Journal of neuroscience research 20010301 |
| Voltage dependence of the [Ca2+](i) oscillations system, in the Mg2+ -stimulated oocyte of the prawn Palaemon serratus. | Cell calcium 20010201 |
| Role of calcium and calmodulin in ciliary stimulation induced by acetylcholine. | American journal of physiology. Cell physiology 20010101 |
| Effects of extracellular calcium and potassium on the sodium pump of rat adrenal glomerulosa cells. | American journal of physiology. Cell physiology 20010101 |
| Inhibition of the type 1 inositol 1,4,5-trisphosphate-sensitive Ca2+ channel by calmodulin antagonists. | Cellular signalling 20010101 |
| Glutamate decarboxylase activity in Trichoderma viride conidia and developing mycelia. | Archives of microbiology 20010101 |
| Inhibition of calcium-independent luminal uptake of L-dopa by calmodulin antagonists in immortalized rat capillary cerebral endothelial cells. | Cell biology international 20010101 |
| Ca2+-independent activation of the endothelial nitric oxide synthase in response to tyrosine phosphatase inhibitors and fluid shear stress. | Circulation research 19980406 |
| Differential effects of omega-conotoxin GVIA, nimodipine, calmidazolium and KN-62 injected intrathecally on the antinociception induced by beta-endorphin, morphine and [D-Ala2,N-MePhe4,Gly-ol5]-enkephalin administered intracerebroventricularly in the mouse. | The Journal of pharmacology and experimental therapeutics 19970801 |
| Enhancement of metallothionein gene expression in male Wistar (WF/NCr) rats by treatment with calmodulin inhibitors: potential role of calcium regulatory pathways in metallothionein induction. | Toxicology and applied pharmacology 19940301 |
| Inhibitors of calmodulin impair the constitutive but not the inducible nitric oxide synthase activity in the rat aorta. | The Journal of pharmacology and experimental therapeutics 19920501 |
| Nerve growth factor-stimulated calcium uptake into PC12 cells: uniqueness of the channel and evidence for phosphorylation. | Journal of neuroscience research 19920401 |
| Purification of cloned trypanosomal calmodulin and preliminary NMR studies. | Journal of chromatography 19910222 |
| Effects of the calmodulin antagonists fendiline and calmidazolium on aggregation, secretion of ATP, and internal calcium in washed human platelets. | Naunyn-Schmiedeberg's archives of pharmacology 19910101 |
| A proton nuclear magnetic resonance and molecular modeling study of calmidazolium (R24571) binding to calmodulin and skeletal muscle troponin C. | The Journal of biological chemistry 19900615 |
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