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C1530

Cyclopiazonic acid

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

Synonym(s):

CPA

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About This Item

Empirical Formula (Hill Notation):
C20H20N2O3
CAS Number:
18172-33-3
Molecular Weight:
336.38
UNSPSC Code:
12352106
PubChem Substance ID:
24892420
NACRES:
NA.77
MDL number:
MFCD00167445
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
200
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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)

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

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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Certificates of Analysis (COA)

Lot/Batch Number
079M4082V
14181112
128M4046V
068M4033V
14180112

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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+
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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Global Trade Item Number

SKUGTIN
C1530-10MG04061833467701
C1530-50MG04061833269510
C1530-5MG04061833467718