CYCLOPIAZONIC ACID

Synonym(s):CPA;Cyclopiazonic Acid, Penicillium cyclopium - CAS 18172-33-3 - Calbiochem

CAS NO.：18172-33-3
Empirical Formula: C20H20N2O3
Molecular Weight: 336.38
MDL number: MFCD00167445
SAFETY DATA SHEET (SDS)
Update Date: 2023-09-04 15:51:00

What is CYCLOPIAZONIC ACID?

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

The Uses of CYCLOPIAZONIC ACID

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.

The Uses of CYCLOPIAZONIC ACID

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.

The Uses of CYCLOPIAZONIC ACID

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

What are the applications of Application

Cyclopiazonic Acid is an inhibitor of endoplasmic reticulum Ca2+-ATPase

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

Properties of CYCLOPIAZONIC ACID

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 for CYCLOPIAZONIC ACID

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06
GHS Hazard Statements	H300:Acute toxicity,oral
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.