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Submit ReviewCyclopiazonic acid
Description: Inhibitor of SERCA ATPase
Alternative Names: α-Cyclopiazonic acid
Chemical Name: (6aR,11aS,11bR)-rel-10-Acetyl-2,6,6a,7,11a,11b-hexahydro-7,7-dimethyl-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
Purity: ≥98% (HPLC)
Biological Activity for Cyclopiazonic acid
Cyclopiazonic acid is a cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca2+-ATPase.
Technical Data for Cyclopiazonic acid
| M. Wt | 336.39 |
| Formula | C20H20N2O3 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 18172-33-3 |
| PubChem ID | 54682463 |
| InChI Key | SZINUGQCTHLQAZ-DQYPLSBCSA-N |
| Smiles | OC([C@](N4C(C)5C)([H])[C@]1([H])[C@@]5([H])CC3=C2C1=CNC2=CC=C3)=C(C(C)=O)C4=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Cyclopiazonic acid
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 33.64 | 100 |
Preparing Stock Solutions for Cyclopiazonic acid
The following data is based on the product molecular weight 336.39. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.97 mL | 14.86 mL | 29.73 mL |
| 5 mM | 0.59 mL | 2.97 mL | 5.95 mL |
| 10 mM | 0.3 mL | 1.49 mL | 2.97 mL |
| 50 mM | 0.06 mL | 0.3 mL | 0.59 mL |
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Product Datasheets for Cyclopiazonic acid
References for Cyclopiazonic acid
References are publications that support the biological activity of the product.
Plenge-Tellechea et al (1997) On the inhibition mechanism of sarcoplasmic or endoplasmic reticulum Ca2+-ATPases by cyclopiazonic acid. J.Biol.Chem. 272 2794 PMID: 9006919
Soler et al (1998) Cyclopiazonic acid effect on Ca2+-dependent conformational states of the sarcoplasmic reticulum ATPase. Implication for the enzyme turnover. Biochemistry 37 4266 PMID: 9521749
Takemoto et al (1998) Comparison of contractions produced by CB, thapsigargin and cyclopiazonic acid in the guinea-pig tracheal muscle. Br.J.Pharmacol. 124 1449 PMID: 9723957
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Keywords: Cyclopiazonic acid, Cyclopiazonic acid supplier, inhibitors, inhibits, SERCA, ATPase, Ca2+, modulators, Ca2+-ATPase, Signaling, Signalling, Calcium, P-Type, ATPases, Calcium-ATPase, Ion, Transporters, Pumps, α-Cyclopiazonic, acid, alpha-Cyclopiazonic, a-Cyclopiazonic, 1235, Tocris Bioscience
16 Citations for Cyclopiazonic acid
Citations are publications that use Tocris products. Selected citations for Cyclopiazonic acid include:
Dwivedi et al (2023) The TMEM16A blockers benzbromarone and MONNA cause intracellular Ca2+-release in mouse bronchial smooth muscle cells Eur J Pharmacol PMID: 36967079
Chai et al (2017) Neural Circuit-Specialized Astrocytes: Transcriptomic, Proteomic, Morphological, and Functional Evidence. Neuron 95 531 PMID: 28712653
Alzayady et al (2013) Fragmented inositol 1,4,5-trisphosphate receptors retain tetrameric architecture and form functional Ca2+ release channels. J Biol Chem 288 11122 PMID: 23479737
Choi et al (2009) Comparison of contractile mechanisms of sphingosylphosphorylcholine and sphingosine-1-phosphate in rabbit coronary artery. PLoS One 82 324 PMID: 19218288
Zhu et al (2015) Intracellular Ca(2+) release from endoplasmic reticulum regulates slow wave currents and pacemaker activity of interstitial cells of Cajal. Am J Physiol Cell Physiol 308 C608 PMID: 25631870
Grey and Burrell (2010) Co-induction of LTP and LTD and its regulation by protein kinases and phosphatases. J Neurophysiol 103 2737 PMID: 20457859
Patel et al (2009) Mobilization of calcium from intracellular stores facilitates somatodendritic DA release. J Neurosci 29 6568 PMID: 19458227
Morais et al (2018) Glycine Receptor Activation Impairs ATP-Induced Calcium Transients in Cultured Cortical Astrocytes. Front Mol Neurosci 10 444 PMID: 29386993
Li et al (2016) Junctophilin 3 expresses in pancreatic beta cells and is required for glucose-stimulated Ins secretion. Cell Death Dis 7 e2275 PMID: 27336719
Elgueta et al (2015) Acetylcholine induces GABA release onto rod bipolar cells through heteromeric nicotinic receptors expressed in A17 amacrine cells. Neuropharmacology 9 6 PMID: 25709566
Fransen et al (2015) Dissecting out the complex Ca2+-mediated phenylephrine-induced contractions of mouse aortic segments. J Neurosci 10 e0121634 PMID: 25803863
Earls et al (2010) Dysregulation of presynaptic calcium and synaptic plasticity in a mouse model of 22q11 deletion syndrome. Front Cell Neurosci 30 15843 PMID: 21106823
Atakpa et al (2018) IP3 Receptors Preferentially Associate with ER-Lysosome Contact Sites and Selectively Deliver Ca2+ to Lysosomes. Cell Rep 25 3180 PMID: 30540949
McQuail et al (2013) Hippocampal Gαq/11 but not Gαo-coupled receptors are altered in aging. Cardiovasc Res 70 63 PMID: 23347951
Eder and Bading (2007) Calcium signals can freely cross the nuclear envelope in hippocampal neurons: somatic calcium increases generate nuclear calcium transients. BMC Neurosci 8 57 PMID: 17663775
Kumar and Foster (2004) Enhanced long-term potentiation during aging is masked by processes involving intracellular calcium stores. J Neurophysiol 91 2437 PMID: 14762159
Do you know of a great paper that uses Cyclopiazonic acid from Tocris? Please let us know.
Reviews for Cyclopiazonic acid
Average Rating: 4.5 (Based on 2 Reviews.)
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Cyclopiazonic Acid Blocks Re-Uptake of Ca2+ Into ER leading to increased T-cell activation by IFNg.
By
Anonymous on 01/23/2019
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: Primary Cd8+ T-cells
Cyclopiazonic acid (CPA) was used to block SERCA in activated CD8+ T-cells. This maintained high intracellular Ca2+, leading to increased activation of CD8+ T-cells as measured by IFNg production via intracellular flow cytometry.
Cyclopiazonic acid (CPA) depletes ER Ca2+ stores, leading to STIM1 clustering in in HEK293 cells..
By
Niroj Shrestha on 11/02/2018
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: HEK293
ER resident protein, STIM1 was expressed with YFP fluorescent tag in HEK293 cells and imaged using TIRF microscopy. STIM1 (left) clusters to form punctae at PM-ER junctions upon ER Ca2+ store depletion (right) by CPA (25 µM in DMSO), thereby activating Orai1-mediated Ca2+ entry.
