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Merck

C1530

Cyclopiazonic acid

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

Sinónimos:

CPA

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Fórmula empírica (notación de Hill):
C20H20N2O3
Número CAS:
Peso molecular:
336.38
NACRES:
NA.77
UNSPSC Code:
12352106
PubChem Substance ID:
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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Nombre del producto

Cyclopiazonic acid from Penicillium cyclopium, ≥98% (HPLC), powder

Quality Level

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

General description

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

Application

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

Biochem/physiol Actions

Inhibits the sarcoplasmic reticulum Ca2+-pump.


pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

Clase de almacenamiento

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges



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G W J Wright et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 24(5), e221-e234 (2012-02-02)
Interstitial cells of Cajal (ICC) associated with the myenteric plexus of the small intestine express maxi chloride channels. Our aim was to investigate whether or not these channels would be activated by increases in intracellular Ca(2+) , as that would
Plant and fungal toxins as contaminants of feed and meat
Improving the Safety of Fresh Meat, 77-101 (2005)
N Demaurex et al.
The Journal of biological chemistry, 267(4), 2318-2324 (1992-02-05)
The filling state of intracellular Ca2+ stores has been proposed to regulate Ca2+ influx across the plasma membrane in a variety of tissues. To test this hypothesis, we have used three structurally unrelated inhibitors of the Ca(2+)-ATPase of intracellular Ca2+