CYCLOPIAZONIC ACID Chemical Properties

Melting point:

245-246°C

Boiling point:

472.86°C (rough estimate)

Density 

1.2171 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

-20°C

solubility 

DMSO: soluble

form 

powder

pka

4.50±1.00(Predicted)

color 

white to off-white

Water Solubility 

Soluble in DMSO (100 mM), ethanol (5 mM), DMF (~20 mg/ml), and 1:1 DMSO:PBS(pH 7.2) (0.5 mg/ml). Insoluble in water.

EPA Substance Registry System

Cyclopiazonic acid (18172-33-3)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

36/37/39-45

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

UY8587000

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29337900

Hazardous Substances Data

18172-33-3(Hazardous Substances Data)

Toxicity

chicken,LD50,oral,12mg/kg (12mg/kg),Poultry Science. Vol. 65(Suppl,

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

CYCLOPIAZONIC ACID Usage And Synthesis

Description

Cyclopiazonic acid is a mycotoxin that has been found in Penicillium and Aspergillus and an inhibitor of sarcoplasmic/endoplasmic reticulum Ca²⁺-ATPase (SERCA; IC₅₀ = 0.6 μM). In vivo, cyclopiazonic acid (11-14 mg/kg) induces ptosis, hypothermia, tremor, and cachexia, as well as induces lethality (LD₅₀ = 13 mg/kg), in rats. It induces tachycardia and sedation in rabbits when administered at a dose of 10 mg/kg.

Chemical Properties

off-white powder or crystals

Uses

Cyclopiazonic acid is a tremorigenic indole produced by several species of Aspergillus and Penicillium. Cyclopiazonic acid is a highly specific inhibitor of calcium ATPase of sarcoplasmic reticulum, altering calcium homeostasis and ATP-dependent calcium transport and resulting in the release of intracellular stored Ca2+ without increasing IP3.

Uses

The use of Cyclopiazonic acid on Langendorff-perfused murine hearts displayed anti-arrhythmic effects. Also, administration of cyclopiazonic acid on rat soleus muscle showed a decrease in hormone sensitive lipase activity and triacylglycerol hydrolysis. It is also used as an inhibitor of endoplasmic reticulum Ca2+-ATPase.

Uses

Cyclopiazonic acid from?Penicillium cyclopium has been used:

• as a standard in aflatoxin detection and quantification by thin layer chromatography (TLC)
• as a component in Ca²⁺-free DMEM/10% fetal bovine serum (FBS)
• as a reversible inhibitor of the sarco/endoplasmic reticulum Ca²⁺-ATPase (SERCA) to examine the role of luminal calcium in endoplasmic recticulum (ER)-to-Golgi trafficking
• as an endoplasmic reticulum Ca²⁺-ATPase blocker, to treat neurons and also to study the role of the endoplasmic reticulum (ER) in releasing and sustaining Ca²⁺?during Ca²⁺-induced Ca²⁺ release (CICR) to inhibit SERCA

General Description

Cyclopiazonic acid (CPA), a tetramic acid is synthesized by various Aspergillus and Penicillium species.

Biological Activity

Cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca 2+ -ATPase.

Biochem/physiol Actions

Inhibits the sarcoplasmic reticulum Ca2+-pump.

storage

-20°C

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