4431-00-9

4431-00-9 structure

Name: Aurintricarboxylic acid
Chemical Name: aurintricarboxylic acid
CAS Number: 4431-00-9
Molecular Formula: C₂₂H₁₄O₉
Molecular Weight: 422.341
Catalog: Chemical reagent Organic reagent fatty acid
Create Date: 2018-06-19 17:33:03
Modify Date: 2024-01-06 13:56:25
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].

Name	aurintricarboxylic acid
Synonyms	Benzoic acid, 5-((3-carboxy-4-hydroxyphenyl)(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methyl)-2-hydroxy- 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) Benzoic acid, 3,3'-[(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis[6-hydroxy- MFCD00011663

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
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.

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	powder \| dark red to brown
Vapour Pressure	0.0±2.7 mmHg at 25°C
Index of Refraction	1.751
Water Solubility	1 M NH4OH: 10 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GU4790000

CHEMICAL NAME :: 1,4-Cyclohexadiene-1-carboxylic acid, 3-(bis(3-carboxy-4-hydroxyphenyl)methylene)-6-oxo-

CAS REGISTRY NUMBER :: 4431-00-9

BEILSTEIN REFERENCE NO. :: 2228904

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C22-H14-O9

MOLECULAR WEIGHT :: 422.36

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 340 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 558 mg/kg/18D-I

TOXIC EFFECTS :: Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Liver

DOSE/DURATION :: 100 umol/L

REFERENCE :: AMOKAG Acta Medicia Okayama. (Okayama Univ. Medical School, Okayama, Japan) V.27 1973- Volume(issue)/page/year: 33,149,1979

Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi: Irritant;
Risk Phrases	36/37/38
Safety Phrases	S26-S36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	GU4790000

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