Aurintricarboxylic acid

Modify Date: 2024-01-06 13:56:25

Aurintricarboxylic acid Structure
Aurintricarboxylic acid structure
Common Name Aurintricarboxylic acid
CAS Number 4431-00-9 Molecular Weight 422.341
Density 1.6±0.1 g/cm3 Boiling Point 759.6±60.0 °C at 760 mmHg
Molecular Formula C22H14O9 Melting Point 300 °C(lit.)
MSDS Chinese USA Flash Point 427.1±29.4 °C

 Use of 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[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].

 Names

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
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
Water Solubility 1  M NH4OH: 10 mg/mL

 Toxicological Information

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

 Safety Information

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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 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
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