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189400

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C22H14O9
CAS Number:
4431-00-9
Molecular Weight:
422.34
MDL number:
MFCD00011663
UNSPSC Code:
12352106
NACRES:
NA.77

Quality Level

100

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

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).
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. Shown to inhibit apoptotic cell death in various cell types induced by a variety of factors. ATA is also a potent inhibitor of DNA topoisomerase II. Inhibits von Willebrand factor binding to platelets and reduces glutamate-induced neuronal injury. ATA has been reported to stimulate the tyrosine phosphorylation of MAP kinases, Shc proteins, phosphatidylinositol 3-kinase, and phospholipase C-γ. Dye content: ~85%.
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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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