454036
Aurintricarboxylic acid ammonium salt
Synonym(s):
ATA, Aluminon, Ammonium aurintricarboxylate
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About This Item
Linear Formula:
C22H14O9 · 3NH3
CAS Number:
Molecular Weight:
473.43
UNSPSC Code:
12171500
EC Number:
209-319-1
Beilstein/REAXYS Number:
3900820
Colour Index Number:
43810
MDL number:
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
mp
220-225 °C (dec.) (lit.)
λmax
450 nm
522 nm (2nd)
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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.
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