18172-33-3

Basic information

• Product Name: CYCLOPIAZONIC ACID
• Synonyms: (6a-alpha,11a,11b-alpha)--10-acetyl-7-dimethyl-11-hydroxy-;9h-pyrrolo(1’,2’:2,3)isoindolo(4,5,6-cd)indol-9-one,2,6,6a,7,11a,11b-hexahydro;(6AA, 10Z, 11AB, 11BA)-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;(6AR,11AS,11BR)-REL-10-ACETYL-2,6,6A,7,11A,11B-HEXAHYDRO-7,7-DIMETHYL-9H-PYRROLO[1',2':2,3]ISOINDOLO[4,5,6-CD]INDOL-9-ONE;ALPHA CYCLOPIAZONIC ACID;CPA;CYCLOPIAZONIC ACID;CYCLOPIAZONIC ACID, PENICILLIUM CYCLOPIUM
• CAS NO: 18172-33-3
• Molecular Formula: C₂₀H₂₀N₂O₃
• Molecular Weight: 336.38
• Product Categories: Calcium signaling;Signalling;antibiotic
• Mol File: 18172-33-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 245-246°C
• Boiling Point: 472.86°C (rough estimate)
• Flash Point: 315.8°C
• Appearance: white to off-white/powder
• Density: 1.2171 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• PKA: 4.50±1.00(Predicted)
• 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.
• CAS DataBase Reference: CYCLOPIAZONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPIAZONIC ACID(18172-33-3)
• EPA Substance Registry System: CYCLOPIAZONIC ACID(18172-33-3)

Safety Data

• Hazard Codes: T
• 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
• Hazardous Substances Data: 18172-33-3(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 18172-33-3 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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 traffickingas 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.