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C1530

Sigma-Aldrich

Cyclopiazonic acid from Penicillium cyclopium

≥98% (HPLC), powder

Synonym(s):

CPA

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About This Item

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

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)

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
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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+
Toxigenic Aspergillus flavus and other fungi of public health concern in food and organic matter in southwest Nigeria
Fapohunda SO, et al.
Mycology, 3, 210-219 (2012)
Ca2+-Induced Ca2+ Release in Aplysia Bag Cell Neurons Requires Interaction Between Mitochondrial and Endoplasmic Reticulum Stores
Geiger JE, et al.
Journal of Neurophysiology (2008)
Sakiko Ujita et al.
Cerebral cortex (New York, N.Y. : 1991), 27(2), 1602-1614 (2016-01-24)
Astrocytes in various brain regions exhibit spontaneous intracellular calcium elevations both in vitro and in vivo; however, neither the temporal pattern underlying this activity nor its function has been fully evaluated. Here, we utilized a long-term optical imaging technique to
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