189400

Aurintricarboxylic Acid

A cell-permeable polyanionic, polyaromatic compound used as a powerful inhibitor of cellular processes that are dependent on the formation of protein-nucleic acid complexes.

• Synonym(s): Aurintricarboxylic Acid, ATA
• Empirical Formula (Hill Notation): C₂₂H₁₄O₉
• CAS Number: 4431-00-9
• Molecular Weight: 422.34
• MDL number: MFCD00011663
• UNSPSC Code: 12352106
• NACRES: NA.77

Properties

• Quality Level: 100
• description: RTECS - GU4790000
• Assay: ≥85% (titration)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: red
• solubility: 0.1 M NaOH: 35 mg/mL
• shipped in: ambient
• storage temp.: 10-30°C
• 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: UDPQMNAHKKTHHI-UHFFFAOYSA-N

Description

General description

A cell-permeable polyanionic, polyaromatic compound used as a powerful inhibitor of cellular processes that are dependent on the formation of protein-nucleic acid complexes. Binds to aFGF and reduces its angiogenic activity. Shown to inhibit apoptotic cell death in various cell types induced by a variety of factors. ATA is a potent inhibitor of DNA topoisomerase II (IC₅₀= 75 nM for the yeast enzyme as measured by relaxation assays) that also acts as a potent inhibitor of angiogenesis. Inhibits von Willebrand factor binding to platelets and reduces glutamate-induced neuronal injury. ATA stimulates the tyrosine phosphorylation of MAP kinases, Shc proteins, phosphatidylinositol 3-kinase, and phospholipase Cγ. Inhibits both major calpain isoforms (IC₅₀ = 22 µM and IC₅₀ = 10 µM for µ-calpain and m-calpain, respectively).

Dye content: ~85%.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
DNA topoisomerase 2

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 75 nM against DNA topoisomerase II

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot, purge with inert gas, and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Lozano, R.M., et al. 1997. Eur. J. Biochem.248, 30.
Benchokroun, Y., et al. 1995. Biochem. Pharmacol.49, 305.
Okada, N., and Koizumi, S. 1995. J. Biol. Chem.270, 16464.
Posner, A., et al. 1995. Biochem. Mol. Biol. Int. 36, 291.
Catchpoole, D.R., et al. 1994. Anticancer Res. 14, 853.
Csernansky, C.A., et al. 1994. J. Neurosci. Res. 38, 101.
Gagliardi, A.R., and Collins, D.C. 1994. Anticancer Res. 14, 475.
Gonzalez, R.G., et al. 1980. Biochemistry19, 4299.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable