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A0885

Sigma-Aldrich

Aurintricarboxylic acid ammonium salt

powder

Synonym(s):

ATA, Aluminon, Ammonium aurintricarboxylate

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About This Item

Linear Formula:
C22H14O9 · 3NH3
CAS Number:
569-58-4
Molecular Weight:
473.43
Colour Index Number:
43810
Beilstein/REAXYS Number:
3900820
EC Number:
209-319-1
MDL number:
MFCD00040925
UNSPSC Code:
12171500
PubChem Substance ID:
24890465
NACRES:
NA.47

biological source

synthetic

form

powder

color

dark red

mp

220-225 °C (dec.) (lit.)

solubility

water: soluble 100 mg/mL, dark red

λmax

552 nm (λmax: )

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

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

InChI

1S/C22H14O9.3H3N/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;;;/h1-9,23-24H,(H,26,27)(H,28,29)(H,30,31);3*1H3

InChI key

AIPNSHNRCQOTRI-UHFFFAOYSA-N

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Application

Aurintricarboxylic acid ammonium salt has been used as a nuclease inhibitor to study its effects on transfection.

Biochem/physiol Actions

Aurintricarboxylic acid 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 C in PC12 cells. Aurintricarboxylic acid inhibits apoptosis in many cell types. Its neuroprotective effect, perhaps due to its ability to prevent down-regulation of Ca2+ impermeable GluR2 receptors or to its ability to inhibit calpain, a Ca2+-activated protease that is activated during apoptosis.

Other Notes

May contain a substantial amount of polymeric material.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Efficient nonviral cutaneous transfection
Glasspool-Malone et al.
Molecular Therapy, 140-146 (2000)
Hui-Chen Hung et al.
The Journal of antimicrobial chemotherapy, 65(4), 676-683 (2010-01-22)
Enterovirus 71 (EV71) causes serious diseases in humans. The aim of this study was to examine the effects of aurintricarboxylic acid (ATA) on EV71 replication and to explore the underlying mechanism. To measure the activity of ATA in inhibiting the
Hui-Chen Hung et al.
Antiviral research, 81(2), 123-131 (2008-11-19)
There is a continuing threat that the highly pathogenic avian influenza virus will cause future influenza pandemics. In this study, we screened a library of compounds that are biologically active and structurally diverse for inhibitory activity against influenza neuraminidase (NA).
Jakyung Yoo et al.
Advances in protein chemistry and structural biology, 87, 219-247 (2012-05-23)
DNA methyltransferases (DNMTs) are promising epigenetic targets for the development of novel anticancer drugs and other diseases. Molecular modeling and experimental approaches are being used to identify and develop inhibitors of human DNMTs. Most of the computational efforts conducted so
Mélanie K Rich et al.
Plant physiology, 168(3), 788-797 (2015-05-15)
Arbuscular mycorrhiza (AM) is a mutual symbiosis that involves a complex symbiotic interface over which nutrients are exchanged between the plant host and the AM fungus. Dozens of genes in the host are required for the establishment and functioning of
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