Cyclopiazonic Acid

Cayman Chemical Item Number 11326

NSC 117181 (CAS 18172-33-3)

Cyclopiazonic Acid (CAS 18172-33-3)

See more

Description

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

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).

Synonyms
  • NSC 117181
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
Molecular Formula C20H20N2O3
Formula Weight 336.4
Formulation A crystalline solid
Purity ≥95%
λmax 224, 281 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CC1(C)​N2C(C(O)​=C(C(C)​=O)​C2=O)​C(C1C3)​C4=CNC5=CC=CC3=C54
InCHI Code
Copy InCHI code to clipboard
​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
Copy InCHI key to clipboard
SZINUGQCTHLQAZ-UHFFFAOYSA-N

Download free InCHI Key generation software

Size Price Quantity Subtotal
1 mg $18.00 $0.00
5 mg $54.00 $0.00
10 mg $96.00 $0.00
Bulk Contact
Cart Total $0.00

Please Login or Register to use this page.

Pricing updated 2014-04-16. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

Deoxynivalenol New
Roquefortine C New
Tenuazonic Acid
Thapsigargin
Show all 4 Hide all but first 3

Downloads

Batch-specific Information

Get batch-specific data and documents by batch number


Separate multiple batch numbers with commas

Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Other Resources
About Cayman Management Team Company Profile ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map Conference Travel Grants

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2014 Cayman Chemical Company

Manufacturer, supplier, and vendor of biochemical reagents, assay kits, forensic chemistry standards, antibodies, and proteins for scientific research · Buy now! · Analytical testing services and custom synthesis also available

Lost password?