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

NACRES:

NA.77

UNSPSC Code:

12352106

PubChem Substance ID:

24892420

MDL number:

MFCD00167445

Product Name

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

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

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: soluble
chloroform: soluble

storage temp.

−20°C

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.

General description

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

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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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)

Ca2+ sensitivity of the maxi chloride channel in interstitial cells of Cajal.

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

cAMP-Dependent Calcium Oscillations of Astrocytes: An Implication for Pathology.

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

Vascular endothelial growth factor stimulates endothelial colony forming cells proliferation and tubulogenesis by inducing oscillations in intracellular Ca2+ concentration.

Silvia Dragoni et al.

Stem cells (Dayton, Ohio), 29(11), 1898-1907 (2011-09-10)

Endothelial progenitor cells (EPCs) home from the bone marrow to the site of tissue regeneration and sustain neovascularization after acute vascular injury and upon the angiogenic switch in solid tumors. Therefore, they represent a suitable tool for cell-based therapy (CBT)

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