CYCLOPIAZONIC ACID Property

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

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,

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

CYCLOPIAZONIC ACID Chemical Properties,Usage,Production

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