CYCLOPIAZONIC ACID
Product ID L8906 
Name CYCLOPIAZONIC ACID 
Molecular formula C20H20N2O3
Description

It is a specific inhibitor of Ca2+-ATPase in the intracellular Ca2+ storage sites.


Mycotoxin, purified from the microorganism Penicillium cyclopium.
Biological activity

CPA is a highly selective inhibitor of Ca2+ - ATPase in skeletal muscle sarcoplasmic reticulum. It
stimulates release of Ca2+ from intracellular stores by increasing plasma membrane Ca2+ permeability without increasing intracellular inositol (1,4,5)-triphosphate levels. inhibits the Ca2+ uptake: by sarcoplasmic vesicles prepared from skeletal muscle, by intracellular stores sites caffeine-sensitive in guinea-pig smooth muscle cells (3μM); IC50 around 0.6 μM in skinned smooth muscle fibres of the longitudinal layer of the guinea-pig ileum.

It causes selective and reversible strong suppression of Ca2+-dependent K+ current in guinea-pig ileal and urinary bladder smooth muscle cells. It is effective in intact cells and can be washed out.
Its mechanism of action may be the following: decreases Ca2+ uptake by the inhibition of Ca2+ -pump in the sarcoplasmic and endoplasmic reticulum, decreases the subsequent Ca2+ release from these storage sites and, thereby, reduces the Ca2+ dependent K+ current.

 Packaging and Prices

Packaging Price (€) Quantité Buy Now
5 mg 46.00

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25 mg 184.00

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 Product Technical Documents
Safety Data Sheet Available on request, please Contact us
Ref. SDS_L8906 : unit price : free of charge
 Chemical and Physical Properties
Product code L8906  Molecular weight 336.39 g/mol
Product name CYCLOPIAZONIC ACID  Physical form white to off-white hygroscopic powder
CAS No. 18172-33-3 Melting point 245 °C
RTECS UY8587000 Solubility Well in chloroform and DMSO
UNIPROT Optical Activity
PubChem SID    
PubChem CID 54682463    
Purity 98%    
Toxicity(LD50) rat (p.o.): 36 mg/kg; (i.p.): 2 mg/kg;
mice (p.o.): 64 mg/kg; (i.p.): 13 mg/kg
   
Chemical Name (6aα,10z, 11aβ, 11bα)-6a,7,11a,11b-tetrahydro-10-(1-hydroxyethylidene)-7,7- dimethyl-6H-pyrrolo [1',2':2,3]isoindolo [4,5,6-cd]indole-9,11 (2H,10H)-dione.    
Storage & Reconstitution
Recommandations

Stable in dry state, store at +4°C, avoiding humidity.


 
Savety Recommandations

For research use only — not intended for food, diagnostic or therapeutic use
Toxic

 
 Bibliographic References
Product code L8906 
Product name CYCLOPIAZONIC ACID 

- Suzuki M. et al., "Cyclopiazonic acid, an inhibitor of the sarcoplasmic reticulum Ca2+-pump, reduces Ca2+-dependent K+ currents in guinea-pig smooth muscle cells." Br. J. Pharmacol. (1992). 107(1):134
- Demaurex N. et al., "Cyclopiazonic acid depletes intracellular Ca2+ stores and activates an influx pathway for divalent cations in HL-60 cells." J. Biol. Chem. (1992). 267(4):2318
- Goeger D.E. et al., "Interaction of cyclopiazonic acid with rat skeletal muscle sarcoplasmic reticulum vesicles. Effect on Ca2+ binding and Ca2+ permeability." Biochem. Pharmacol. (1989). 38:3995-4003
- Goeger D.E. et al., "Cyclopiazonic acid inhibition of the Ca2+-transport ATPase in rat skeletal muscle sarcoplasmic reticulum vesicles." Biochem. Pharmacol. (1988). 37:978-981
- Uyama Y. et al., "Effects of cyclopiazonic acid, a novel Ca2+-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle." Br. J. Pharmacol. (1992). 106(1):208-214
- Iino M., "Calcium-induced calcium release mechanism in guinea pig taenia caeci." J. Gen. Physiol. (1989). 94:363-383
 Links
Product code L8906 
Product name CYCLOPIAZONIC ACID 
External Links PubMed
Biomedical Citations From PubMed
Toxicology Citations From PubMed
PubChem CID
Molecular formula

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