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: 2024-10-31 18:15:48
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. |
Computed Descriptors for CYCLOPIAZONIC ACID
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