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A8486

Sigma-Aldrich

N-(p-Amylcinnamoyl)anthranilic acid

≥98% (HPLC)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C21H23NO3
Numéro CAS:
99196-74-4
Poids moléculaire :
337.41
Numéro MDL:
MFCD00211365
Code UNSPSC :
12352106
ID de substance PubChem :
329770958
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: ≥20 mg/mL

Température de stockage

room temp

Chaîne SMILES 

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+

Clé InChI

GAMRBCZMOOMBSQ-CCEZHUSRSA-N

Description générale

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.

Application

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.

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Pictogrammes

Environment
GHS09

Mention d'avertissement

Warning

Mentions de danger

H410

Conseils de prudence

P273 - P391 - P501

Classification des risques

Aquatic Acute 1 - Aquatic Chronic 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Anthranilic acid reagent grade, ≥98%

Sigma-Aldrich

A89855

Anthranilic acid

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
Arif Demirdaş et al.
Cellular and molecular neurobiology, 37(1), 133-144 (2016-03-05)
Calcium ions (Ca
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
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Articles

Phospholipase A2

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.

Transient Receptor Potential Channels

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