Aurintricarboxylic acid

Aurintricarboxylic acid is a nanomolar-potency, allosteric antagonist with selectivity towards αβ-methylene-ATP-sensitive P2X1Rs and P2X3Rs, with IC50s of 8.6 nM and 72.9 nM for rP2X1R and rP2X3R, respectively. Aurintricarboxylic acid is a potent anti-influenza agent by directly inhibiting the neuraminidase. Aurintricarboxylic acid is an inhibitor of topoisomerase II and apoptosis. Aurintricarboxylic acid is a selective inhibitor of the TWEAK-Fn14 signaling pathway. Aurintricarboxylic acid also acts as a cystathionine-lyase (CSE) inhibitor with an IC50 of 0.6 μM[5]. Aurintricarboxylic acid is a modifier of miRNAs that regulate miRNA function, with an IC50 of 0.47 µM.

Product information

CAS Number: 4431-00-9

Molecular Weight: 422.34

Formula: C22H14O9

Chemical Name: 5-[(3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxocyclohexa-2, 5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid

Smiles: OC(=O)C1=CC(C=CC1=O)=C(C1=CC(=C(O)C=C1)C(O)=O)C1=CC(=C(O)C=C1)C(O)=O

InChiKey: GIXWDMTZECRIJT-UHFFFAOYSA-N

InChi: InChI=1S/C22H14O9/c23-16-4-1-10(7-13(16)20(26)27)19(11-2-5-17(24)14(8-11)21(28)29)12-3-6-18(25)15(9-12)22(30)31/h1-9,23-24H,(H,26,27)(H,28,29)(H,30,31)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 125 mg/mL (295.97 mM; Need ultrasonic) H2O : < 0.1 mg/mL (ultrasonic) (insoluble)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Aurintricarboxylic acid weakly inhibits P2X2/3Rs, P2X2Rs, P2X4Rs or P2X7Rs. Aurintricarboxylic acid inhibits ATP-induced currents in a concentration dependent manner. Aurintricarboxylic acid can inhibit the severe acute respiratory syndrome-associated coronavirus (SARS-CoV) and vaccinia virus. Aurintricarboxylic acid inhibits replication of influenza A and B viruses by inhibition of neuraminidase activities. Aurintricarboxylic acid inhibits TWEAK-Fn14-mediated NF-κB activation. Aurintricarboxylic acid (10 μM; 0.5-2 hours) suppresses TWEAK-Fn14-mediated NF-κB, Akt, and Src phosphorylation in GBM cells. Aurintricarboxylic acid represses TWEAK-stimulated glioma cell migration and invasion without causing cell cytotoxicity. Aurintricarboxylic acid (Compound 8) cannot regulate loading of endogenous let-7 onto AGO2 inside cultured cells, whereas can inhibit RISC loading of exogenous siRNA.

References:

1. Obrecht AS, et al. Identification of aurintricarboxylic acid as a potent allosteric antagonist of P2X1 and P2X3 receptors. Neuropharmacology. 2019 Nov 1;158:107749.
2. Hashem AM, et al. Aurintricarboxylic acid is a potent inhibitor of influenza A and B virus neuraminidases. PLoS One. 2009 Dec 17;4(12):e8350.
3. Benchokroun Y, et al. Aurintricarboxylic acid, a putative inhibitor of apoptosis, is a potent inhibitor of DNA topoisomerase II in vitro and in Chinese hamster fibrosarcoma cells. Biochem Pharmacol. 1995 Jan 31;49(3):305-13.
4. Alison Roos, et al. Identification of aurintricarboxylic acid as a selective inhibitor of the TWEAK-Fn14 signaling pathway in glioblastoma cells. Oncotarget. 2017 Feb 14; 8(7): 12234–12246.

Products are for research use only. Not for human use.