Cyclopiazonic acid

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Cat.No. 1235 - Cyclopiazonic acid | C20H20N2O3 | CAS No. 18172-33-3
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)
Datasheet
Citations (12)
Reviews

Biological Activity

Cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca2+-ATPase.

Technical Data

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 1.68 5 with gentle warming
DMSO 33.64 100

Preparing Stock Solutions

The following data is based on the product molecular weight 336.39. Batch specific molecular weights may vary from batch to batch due to solvent 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

Certificate of Analysis / Product Datasheet
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References

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 carbachol, thapsigargin and cyclopiazonic acid in the guinea-pig tracheal muscle. Br.J.Pharmacol. 124 1449 PMID: 9723957


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12 Citations for Cyclopiazonic acid

Citations are publications that use Tocris products. Selected citations for Cyclopiazonic acid include:

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

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

Li et al (2016) Junctophilin 3 expresses in pancreatic beta cells and is required for glucose-stimulated insulin 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

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 dopamine release. J Neurosci 29 6568 PMID: 19458227

Kumar and Foster (2004) Enhanced long-term potentiation during aging is masked by processes involving intracellular calcium stores. J Neurophysiol 91 2437 PMID: 14762159

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

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

McQuail et al (2013) Hippocampal Gαq/11 but not Gαo-coupled receptors are altered in aging. Cardiovasc Res 70 63 PMID: 23347951


Do you know of a great paper that uses Cyclopiazonic acid from Tocris? Please let us know.

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