CAS Number4431-00-9
Synonyms3,3'-[(3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(6-hydroxybenzoic acid); Aurintricarboxylic acid; 3,3'-[(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methanediyl]bis(6-hydroxybenzoic acid); EINECS 224-628-1; 3,3'-[(3-Carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis(6-hydroxybenzoic acid); MFCD00011663
Molecular FormulaC22H14O9
Molecular Weight422.34
Purity96.00%%
Density1.6±0.1 g/cm3
Boiling Point759.6±60.0 °C at 760 mmHg
Melting Point300 °C(lit.)
Appearancepowder | dark red to brown
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 4431-00-9 |
| Catalog No. | 2A-9092944 |
| Chinese Name | 金黄三羧酸 |
| Synonyms | 3,3'-[(3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(6-hydroxybenzoic acid); Aurintricarboxylic acid; 3,3'-[(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methanediyl]bis(6-hydroxybenzoic acid); EINECS 224-628-1; 3,3'-[(3-Carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis(6-hydroxybenzoic acid); MFCD00011663 |
| Molecular Formula | C22H14O9 |
| Molecular Weight | 422.34 |
| Purity | 96.00% |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 759.6±60.0 °C at 760 mmHg |
| Melting Point | 300 °C(lit.) |
| Appearance | powder | dark red to brown |
| Water Solubility | 1 M NH4OH: 10 mg/mL |
| Storage Condition | Keep away from light, in a ventilated and dry plac |
| Application | Aurintricarboxylic acid is a highly potent, αβ-methylene-ATP sensitive and selective allosteric antagonist of P2X1Rs and P2X3Rs, with IC50 values of 8.6 nM and 72.9 nM for rP2X1R and rP2X3R, respect |
| PubChem ID | 24278210 |
| SMILES | O=C(O)C1=CC(=C(c2ccc(O)c(C(=O)O)c2)c2ccc(O)c(C(=O)O)c2)C=CC1=O |
| InChI | InChI=1S/C22H16O9.3H3N/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;;;/h1-10,19,24-25H,(H,26,27)(H,28,29)(H,30,31);3*1H3 |
| InChI Key | GIXWDMTZECRIJT-UHFFFAOYSA-N |
| Hazard Symbols | transportation |
| Bioactivity | 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[1]. Aurintricarboxylic acid is a potent anti-influenza agent by directly inhibiting the neuraminidase[2]. Aurintricarboxylic acid is an inhibitor of topoisomerase II and apoptosis[3]. Aurintricarboxylic acid is a selective inhibitor of the TWEAK-Fn14 signaling pathway[4]. Related Catalog Signaling Pathways >> Anti-infection >> Influenza Virus Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Infection Research Areas >> Inflammation/Immunology Signaling Pathways >> Membrane Transporter/Ion Channel >> P2X Receptor Research Areas >> Neurological Disease Target Topoisomerase II rP2X1R:8.6 nM (IC50) rP2X3R:72.9 nM (IC50) Apoptosis In Vitro Aurintricarboxylic acid strongly inhibits rP2X1Rs and rP2X3Rs with IC50 values of 8.6 nM and 72.9 nM, respectively, and more weakly inhibits P2X2/3Rs, P2X2Rs, P2X4Rs or P2X7Rs[1]. Aurintricarboxylic acid inhibition of ATP-induced currents is concentration dependent[1]. Aurintricarboxylic acid is a non-competitive antagonist of P2X3R[1]. Aurintricarboxylic acid can inhibit the severe acute respiratory syndrome-associated coronavirus (SARS-CoV) and vaccinia virus[2]. Aurintricarboxylic acid protects MDCK cells from infection with influenza A strains PR8, NY or N[2]. Aurintricarboxylic acid inhibits replication of influenza A and B viruses[2]. Aurintricarboxylic acid inhibits neuraminidase activities of influenza A and B viruses[2]. Aurintricarboxylic acid inhibits TWEAK-Fn14-mediated NF-κB activation[4]. Aurintricarboxylic acid (10 μM;0.5-2 hours) suppresses TWEAK-Fn14-mediated NF-κB, Akt, and Src phosphorylation in GBM cells[4]. Aurintricarboxylic acid blocks TWEAK-stimulated Rac1 activation and TRAF2 recruitment to Fn14 cytoplasmic domain in glioma cells[4]. Aurintricarboxylic acid represses TWEAK-stimulated glioma cell migration and invasion without causing cell cytotoxicity[4]. Western Blot Analysis[4] Cell Line: T98G, A172, GBM44 glioma cells Concentration: 10 μM Incubation Time: 0.5 hour, 1 hour, 2 hours Result: Abrogated TWEAK activation of downstream signals including phosphorylation of the NF-κB family member p65, Akt, and Src in all three GBM cell lines. 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]. 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. Chemical & Physical Properties Density 1.6±0.1 g/cm3 Boiling Point 759.6±60.0 °C at 760 mmHg Melting Point 300 °C(lit.) Molecular Formula C22H14O9 Molecular Weight 422.341 Flash Point 427.1±29.4 °C Exact Mass 422.063782 PSA 169.43000 LogP 4.09 Appearance of Characters powder | dark red to brown Vapour Pressure 0.0±2.7 mmHg at 25°C Index of Refraction 1.751 InChIKey GIXWDMTZECRIJT-UHFFFAOYSA-N SMILES O=C(O)C1=CC(=C(c2ccc(O)c(C(=O)O)c2)c2ccc(O)c(C(=O)O)c2)C=CC1=O Water Solubility 1 M NH4OH: 10 mg/mL |
| Use of | 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[1]. Aurintricarboxylic acid is a potent anti-influenza agent by directly inhibiting the neuraminidase[2]. Aurintricarboxylic acid is an inhibitor of topoisomerase II and apoptosis[3]. Aurintricarboxylic acid is a selective inhibitor of the TWEAK-Fn14 signaling pathway[4]. Properties Articles78 Name aurintricarboxylic acid Synonym More Synonyms Aurintricarboxylic acid Biological Activity Description 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[1]. Aurintricarboxylic acid is a potent anti-influenza agent by directly inhibiting the neuraminidase[2]. Aurintricarboxylic acid is an inhibitor of topoisomerase II and apoptosis[3]. Aurintricarboxylic acid is a selective inhibitor of the TWEAK-Fn14 signaling pathway[4]. Related Catalog Signaling Pathways >> Anti-infection >> Influenza Virus Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Infection Research Areas >> Inflammation/Immunology Signaling Pathways >> Membrane Transporter/Ion Channel >> P2X Receptor Research Areas >> Neurological Disease Topoisomerase II rP2X1R:8.6 nM (IC50) rP2X3R:72.9 nM (IC50) 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]. 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. Chemical & Physical Properties Molecular Formula C22H14O9 Exact Mass 422.063782 PSA 169.43000 Appearance of Characters powder | dark red to brown Index of Refraction 1.751 InChIKey GIXWDMTZECRIJT-UHFFFAOYSA-N |
| Transport Info | Product name: Purity: 85.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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