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A1895

Sigma-Aldrich

Aurintricarboxylic acid

≥85% purity (titration), practical grade, powder

Synonym(s):

ATA

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About This Item

Empirical Formula (Hill Notation):
C22H14O9
CAS Number:
4431-00-9
Molecular Weight:
422.34
EC Number:
224-628-1
MDL number:
MFCD00011663
UNSPSC Code:
12171500
PubChem Substance ID:
24278210
NACRES:
NA.47

product name

Aurintricarboxylic acid, practical grade, ≥85% (titration), powder

grade

practical grade

Quality Level

300

Assay

≥85% (titration)

form

powder

color

red to very dark red, and Red-Brown andBrown-Red

mp

300 °C (lit.)

solubility

1 M NH4OH: 10 mg/mL

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

OC(=O)c1cc(ccc1O)C(\c2ccc(O)c(c2)C(O)=O)=C3\C=CC(=O)C(=C3)C(O)=O

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)

InChI key

GIXWDMTZECRIJT-UHFFFAOYSA-N

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Application

  • Aurintricarboxylic acid has been used to show its anticryptosporidial activity against Cryptosporidium parvum.
  • It has been used as a test substance to identify inhibitors against coronavirus N7-MTases (guanine-N7-methyltransferase).
  • It has been used as a ribonuclease inhibitor.

Biochem/physiol Actions

Readily polymerizes in aqueous solution, forming a stable free radical that inhibits protein-nucleic acid interactions. It is a potent inhibitor of ribonuclease and topoisomerase II by preventing the binding of the nucleic acid to the enzyme. It stimulates tyrosine phosphorylation processes including the Jak2/STAT5 pathway in NB2 lymphoma cells, ErbB4 in neuroblastoma cells, and MAP kinases, Shc proteins, phosphatidylinositide 3-kinase and phospholipase Cγ in PC12 cells. Inhibits apoptosis. It prevents down-regulation of Ca2+ -impermeable GluR2 receptors and inhibits calpain, a Ca2+ -activated protease that is activated during apoptosis.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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In vitro and in vivo activity of aurintricarboxylic acid preparations against Cryptosporidium parvum.
Klein P, et al.
The Journal of Antimicrobial Chemotherapy, 62, 1101-1104 (2008)
Red Light-Independent Instability of Oat Phytochrome mRNA in Vivo.
Seeley KA, et al.
Plant Cell, 4, 29-38 (1992)
Yeast-based assays for the high-throughput screening of inhibitors of coronavirus RNA cap guanine-N7-methyltransferase.
Sun Y, et al.
Antiviral Research, 104, 156-164 (2014)
Fumihito Noguchi et al.
Molecular cancer therapeutics, 16(5), 936-947 (2017-02-23)
Extracellular acidity is a hallmark of cancers and is independent of hypoxia. Because acidity potentiates malignant phenotypes, therapeutic strategies that enhance the targeting of oncogenic mechanisms in an acidic microenvironment should be effective. We report here that drugs which abrogate
Giuseppe Manfroni et al.
Bioorganic & medicinal chemistry, 20(2), 866-876 (2011-12-27)
Hepatitis C virus (HCV) infection has been recognized as the major cause of liver failure that can lead to hepatocellular carcinoma. Among all the HCV proteins, NS5B polymerase represents a leading target for drug discovery strategies. Herein, we describe our
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