yingweiwo

Aurintricarboxylic acid

Alias: Aurintricarboxylic acid ATA NSC 4056 NSC4056 NSC-4056
Cat No.:V9200 Purity: ≥98%
Aurintricarboxylic acid is a potent, αβ-methylene-ATP sensitive and selective allosteric antagonist of P2X1Rs and P2X3Rs, with IC50s of 8.6 nM and 72.9 nM for rP2X1R and rP2X3R respectively.
Aurintricarboxylic acid
Aurintricarboxylic acid Chemical Structure CAS No.: 4431-00-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
Other Sizes

Other Forms of Aurintricarboxylic acid:

  • Aluminon
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Product Description
Aurintricarboxylic acid is a potent, αβ-methylene-ATP sensitive and selective allosteric antagonist of 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 that acts by directly inhibiting neuraminidase. Aurintricarboxylic acid is also an inhibitor (blocker/antagonist) of topoisomerase II and apoptosis. Aurintricarboxylic acid is a selective inhibitor of the TWEAK-Fn14 signaling pathway. Aurintricarboxylic acid is also a cystathionine-γ-lyase (CSE) inhibitor (antagonist) with IC50 of 0.6 μM. Aurintricarboxylic acid is a miRNA modulator that can modulate the function of miRNA.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
P2X2/3Rs, P2X2Rs, P2X4Rs, or P2X7Rs are all slightly inhibited by aurine tricarboxylic acid[1]. In a concentration-dependent manner, auricin tricarboxylic acid suppresses the current of ATP activation [1]. via controlling the action of calcineurin [2]. Aurin tricarboxylic acid suppresses TWEAK-Fn14 in a weak manner. In GBM cells, aurin tricarboxylic acid (10 μM; 0.5-2 hours) suppresses NF-κB, Akt, and Src phosphorylation mediated by TWEAK-Fn14 [4]. Aurin tricarboxylic acid inhibits TWEAK and stimulates gold tricarboxylic acid (compound 8), which can prevent exogenous siRNA from being loaded by RISC but cannot control endogenous let-7 loading on AGO2 in cultivated cells [4].
Cell Assay
Western Blot analysis [4]
Cell Types: T98G, A172, GBM44 glioma cells
Tested Concentrations: 10 μM
Incubation Duration: 0.5 hrs (hours), 1 hour, 2 hrs (hours)
Experimental Results: Abolition of the activation of TWEAK downstream signals, including phospholipids of the NF-κB family 6]. members p65, Akt, and Src in all three GBM cell lines.
References

[1]. Identification of aurintricarboxylic acid as a potent allosteric antagonist of P2X1 and P2X3 receptors. Neuropharmacology. 2019 Nov 1;158:107749.

[2]. Aurintricarboxylic acid is a potent inhibitor of influenza A and B virus neuraminidases. PLoS One. 2009 Dec 17;4(12):e8350.

[3]. 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]. 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.

[5]. Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase. J Med Chem. 2019 Feb 14;62(3):1677-1683.

[6]. Small molecules with big roles in microRNA chemical biology and microRNA-targeted therapeutics. RNA Biol. 2019 Jun; 16(6): 707-718.

Additional Infomation
Aurintricarboxylic acid is a member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'. It has a role as a histological dye, an insulin-like growth factor receptor 1 antagonist and a fluorochrome. It is a monohydroxybenzoic acid, a member of quinomethanes and a tricarboxylic acid. It is a conjugate acid of an aurintricarboxylate.
A dye which inhibits protein biosynthesis at the initial stages. The ammonium salt (aluminon) is a reagent for the colorimetric estimation of aluminum in water, foods, and tissues.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H14O9
Molecular Weight
422.35
Exact Mass
422.063
CAS #
4431-00-9
Related CAS #
13186-45-3 (tri-hydrochloride salt);569-58-4 (tri-ammonium salt);63451-31-0 (calcium (2:3) salt);93480-02-5 (calcium (1:3) salt)
PubChem CID
2259
Appearance
Brown to black solid powder
Density
1.6±0.1 g/cm3
Boiling Point
759.6±60.0 °C at 760 mmHg
Melting Point
300 °C(lit.)
Flash Point
427.1±29.4 °C
Vapour Pressure
0.0±2.7 mmHg at 25°C
Index of Refraction
1.751
LogP
4.09
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
5
Heavy Atom Count
31
Complexity
841
Defined Atom Stereocenter Count
0
InChi Key
GIXWDMTZECRIJT-UHFFFAOYSA-N
InChi Code
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)
Chemical Name
5-[(3-Carboxy-4-hydroxyphenyl)-(3-carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2-hydroxybenzoic acid
Synonyms
Aurintricarboxylic acid ATA NSC 4056 NSC4056 NSC-4056
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~295.97 mM)
NH4OH : 10 mg/mL (~23.68 mM)
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.92 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (4.92 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3677 mL 11.8385 mL 23.6770 mL
5 mM 0.4735 mL 2.3677 mL 4.7354 mL
10 mM 0.2368 mL 1.1839 mL 2.3677 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Contact Us