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C1530

Cyclopiazonic acid

Name: Cyclopiazonic acid
Brand: SIGMA

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)

Related Categories

Bioactive Small Molecules

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

GHS06

signalword

Danger

hcodes

H300

pcodes

P264 - P270 - P301 + P310 - P405 - P501

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

0000486098

0000477749

0000477748

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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)

Cyclopiazonic acid depletes intracellular Ca2+ stores and activates an influx pathway for divalent cations in HL-60 cells.

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+

Plant and fungal toxins as contaminants of feed and meat

Improving the Safety of Fresh Meat, 77-101 (2005)

Positive Feedback Mechanisms among Local Ca Releases, NCX, and ICaL Ignite Pacemaker Action Potentials.

Alexey E Lyashkov et al.

Biophysical journal, 114(5), 1176-1189 (2018-03-15)

Recent data suggest that cardiac pacemaker cell function is determined by numerous time-, voltage-, and Ca-dependent interactions of cell membrane electrogenic proteins (M-clock) and intracellular Ca cycling proteins (Ca-clock), forming a coupled-clock system. Many aspects of the coupled-clock system, however

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Global Trade Item Number

SKU	GTIN
C1530-10MG	04061833467701
C1530-50MG	04061833269510
C1530-5MG	04061833467718

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