C1530

Cyclopiazonic acid

from Penicillium cyclopium, ≥98% (HPLC), powder, sarcoplasmic reticulum Ca²⁺-pump inhibitor

• Synonym(s): CPA
• Empirical Formula (Hill Notation): C₂₀H₂₀N₂O₃
• CAS Number: 18172-33-3
• Molecular Weight: 336.38
• MDL number: MFCD00167445
• UNSPSC Code: 12352106
• PubChem Substance ID: 24892420
• NACRES: NA.77

Properties

• Product Name: Cyclopiazonic acid from Penicillium cyclopium, ≥98% (HPLC), powder
• Quality Level: 200
• Assay: ≥98% (HPLC)
• form: powder
• color: white to off-white
• solubility: DMSO: soluble; chloroform: soluble
• storage temp.: −20°C
• SMILES string: CN1C(=O)C(=C(\C)O)\C(=O)C2C(Cc3cccc4[nH]cc2c34)C1(C)C
• InChI: 1S/C20H22N2O3/c1-10(23)15-18(24)17-12-9-21-14-7-5-6-11(16(12)14)8-13(17)20(2,3)22(4)19(15)25/h5-7,9,13,17,21,23H,8H2,1-4H3/b15-10-
• InChI key: WJCPGKDPOYBOOJ-GDNBJRDFSA-N
• Gene Information: human ... ADORA1(134) , ADORA2A(135) , ADORA3(140) ; mouse ... Adora1(11539) ; rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

Description

General description

Cyclopiazonic acid (CPA), a tetramic acid is synthesized by various Aspergillus and Penicillium species.[1]

Application

Cyclopiazonic acid from Penicillium cyclopium has been used:

• as a standard in aflatoxin detection and quantification by thin layer chromatography (TLC)[2]
• as a component in Ca²⁺-free DMEM/10% fetal bovine serum (FBS)[3]
• 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[3]
• 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)[4] to inhibit SERCA[5]

Biochem/physiol Actions

Inhibits the sarcoplasmic reticulum Ca²⁺-pump.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves