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Key Documents

A8486

Sigma-Aldrich

N-(p-Amylcinnamoyl)anthranilic acid

≥98% (HPLC)

Sinonimo/i:

2-[[1-oxo-3-(4-Pentylphenyl)-2-propen-1-yl]amino]-benzoic acid, ACA, N-(4-Pentylcinnamoyl)anthranilic acid

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About This Item

Formula empirica (notazione di Hill):
C21H23NO3
Numero CAS:
Peso molecolare:
337.41
Numero MDL:
Codice UNSPSC:
12352106
ID PubChem:
NACRES:
NA.77

Livello qualitativo

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

white to off-white

Solubilità

DMSO: ≥20 mg/mL

Temperatura di conservazione

room temp

Stringa SMILE

CCCCCc1ccc(\C=C\C(=O)Nc2ccccc2C(O)=O)cc1

InChI

1S/C21H23NO3/c1-2-3-4-7-16-10-12-17(13-11-16)14-15-20(23)22-19-9-6-5-8-18(19)21(24)25/h5-6,8-15H,2-4,7H2,1H3,(H,22,23)(H,24,25)/b15-14+
GAMRBCZMOOMBSQ-CCEZHUSRSA-N

Descrizione generale

N-(p-Amylcinnamoyl)anthranilic acid (ACA) functions as a broad spectrum phospholipase A2 inhibitor and blocks transient receptor potential (TRP) channels. It inhibits calcium activated chloride current in cardiac ventricular myocytes. ACA regulates various ion channels.

Applicazioni

N-(p-Amylcinnamoyl)anthranilic acid has been used as a transient receptor potential cation channel subfamily M member 2 (TRPM2) inhibitor, in studying its role in regulating the production of reactive oxygen species (ROS).
N-(p-Amylcinnamoyl)anthranilic acid is a broad spectrum PLA2 inhibitor and TRP channel blocker. N-(p-Amylcinnamoyl)anthranilic acid has been used to study the functional expression of TRPM2 channels in dopaminergic SNc neurons.

Azioni biochim/fisiol

Broad spectrum phospholipase A2 (PLA2) inhibitor and TRP channel blocker.

Caratteristiche e vantaggi

This compound is featured on the Phospholipase A2 page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pittogrammi

Environment

Avvertenze

Warning

Indicazioni di pericolo

Consigli di prudenza

Classi di pericolo

Aquatic Acute 1 - Aquatic Chronic 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


Certificati d'analisi (COA)

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N-(p-amylcinnamoyl) anthranilic acid (ACA): a phospholipase A2 inhibitor and TRP channel blocker
Harteneck C, et al.
Cardiovascular Drug Reviews, 25(1), 61-75 (2007)
Bo Pang et al.
Pflugers Archiv : European journal of physiology, 463(2), 309-318 (2011-10-25)
Sustained increase in [Ca(2+)](c) (Δ[Ca(2+)](c)) is a critical early signal from T-cell receptor (TCR/CD3). In general, Ca(2+)-release activated Ca(2+) channels (CRAC) are responsible for the Ca(2+) influx and Δ[Ca(2+)](c) after TCR/CD3 stimulation. However, T cells also express Ca(2+)-permeable nonselective cation
A dual role of transient receptor potential melastatin 2 channel in cytotoxicity induced by silica nanoparticles
Yu P, et al.
Scientific Reports, 5, 18171-18171 (2015)
Mathias Gelderblom et al.
Stroke, 45(11), 3395-3402 (2014-09-23)
Brain injury during stroke results in oxidative stress and the release of factors that include extracellular Ca(2+), hydrogen peroxide, adenosine diphosphate ribose, and nicotinic acid adenine dinucleotide phosphate. These alterations of the extracellular milieu change the activity of transient receptor

Articoli

Phospholipase A2 (PLA2) designates a class of enzymes that hydrolyze the sn-2 ester of glycerophospholipids to produce a fatty acid and a lysophospholipid. It has become clear that some of these enzymes liberate arachidonic acid in mammalian cells for the biosynthesis of eicosanoids, and thus there has been considerable interest in developing PLA2 inhibitors. Based on amino acid sequences, there are now more than 12 distinct groups of mammalian PLA2s, as well as many non-mammalian forms, all of which have been classified into 14 distinct groups with many subgroups.

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