Cyclopiazonic Acid
Item № 11326
CAS № 18172-33-3
Purity ≥95%
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1 mg $18.00 $0.00
5 mg $54.00 $0.00
10 mg $96.00 $0.00

Pricing updated 2016-05-24. Prices are subject to change without notice.

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Description
Synonyms
  • NSC 117181

Cyclopiazonic acid is a mycotoxin produced by molds including certain species of Penicillium and Aspergillus. Its toxicity is linked to its ability to specifically and reversibly inhibit sarco-endoplasmic reticulum Ca2+-ATPases (SERCA; IC50 = 0.6 μM).1,2 Cyclopiazonic acid does not inhibit a wide variety of other types of membrane-bound ATPases. It effectively inhibits SERCA in intact tissue, in smooth muscle and endothelium, as well as in isolated cells.3,4

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Technical Information
Formal Name 10-acetyl-2,6,6aR,7,11aS,11bR-hexahydro-11-hydroxy-7,7-dimethyl-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
CAS Number 18172-33-3
Synonyms
  • NSC 117181
Molecular Formula C20H20N2O3
Formula Weight 336.4
Purity ≥95%
Formulation A crystalline solid
λmax 224, 281 nm
SMILES CC1(C)N2C(C(O)=C(C(C)=O)C2=O)C(C1C3)C4=CNC5=CC=CC3=C54
InChI Code 1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3
InChI Key SZINUGQCTHLQAZ-UHFFFAOYSA-N

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
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Additional Information

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References & Background Reading
Product Description References

1. Seidler, N.W., Jona, I., Vegh, M., et al. Cyclopiazonic acid is a specific inhibitor of the Ca2+-ATPase of sarcoplasmic reticulum. J Biol Chem 264(30) 17816-17823 (1989).

2. Uyama, Y., Imaizumi, Y., and Watanabe, M. Effects of cyclopiazonic acid, a novel Ca2+-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle. Br J Pharmacol 106 208-214 (1992).

3. Mumtaz, S., Burdyga, G., Borisova, L., et al. The mechanism of agonist induced Ca2+ signalling in intact endothelial cells studied confocally in in situ arteries. Cell Calcium 49(1-4) 66-77 (2011).

4. Berra-Romani, R., Raqeeb, A., Torres-Jácome, J., et al. The mechanism of injury-induced intracellular calcium concentration oscillations in the endothelium of excised rat aorta. J Vasc Res 49 65-76 (2012).

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