Aurintricarboxylic acid

Aurintricarboxylic acid

Names
Preferred IUPAC name 3,3'-[(3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(6-hydroxybenzoic acid)
Other names 5,5'-[(3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(2-hydroxybenzoic acid) Aluminon free acid
Identifiers
CAS Number	4431-00-9 Y
3D model (JSmol)	Interactive image Interactive image
Abbreviations	ATA
ChEBI	CHEBI:87397 N
ChEMBL	ChEMBL275938 Y
ChemSpider	2172 Y 323088 (tautomeric form) Y
ECHA InfoCard	100.022.390
PubChem CID	2259
UNII	NP9O8E29QW Y
CompTox Dashboard (EPA)	DTXSID9063453
InChI 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) Y Key: GIXWDMTZECRIJT-UHFFFAOYSA-N Y InChI=1/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) Key: GIXWDMTZECRIJT-UHFFFAOYAI
SMILES C1=CC(=C(C=C1C(=C2C=CC(=O)C(=C2)C(=O)O)C3=CC(=C(C=C3)O)C(=O)O)C(=O)O)O O=C(O)\C1=C\C(\C=C/C1=O)=C(/c2ccc(O)c(C(=O)O)c2)c3ccc(O)c(C(=O)O)c3
Properties
Chemical formula	C22H14O9
Molar mass	422.345 g·mol−1
Appearance	Dark red to brown powder
Melting point	300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Aurintricarboxylic acid (ATA) is a chemical compound that 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. It also inhibits apoptosis. It prevents down-regulation of Ca²⁺-impermeable GluR2 receptors and inhibits calpain, a Ca²⁺-activated protease that is activated during apoptosis.

It is used to inhibit protein biosynthesis in its initial stages. Nominally, it is used in biological experiments as a protein inhibitor, and as an ammonium salt (known as aluminon) it is used as a reagent to estimate the aluminium in water, biological tissue, and foods.

It was found that ATA is a strong inhibitor of topoisomerases and other nucleases. It might be useful for increasing efficiency of RNA isolation.

It has been discovered that using aurintricarboxylic acid against influenza-A post-infection has a strong protective effect by inhibiting the virus' ability to reproduce. In cultured canine kidney cells, it was found to reduce viral reproduction and infection when applied post-infection, but not when used as a 'vaccine'. It has also been shown to block the binding of the HIV coat molecule gp120 to the CD4 co-receptor on T cells through which it invades.

Aurintricarboxylic acid and its ammonium salt shows antiviral activity in vitro against coronaviruses such as SARS, MERS and SARS-CoV-2, and while it is unlikely to have suitable properties to be developed as a medicine in its own right, it has proved useful in scientific research into novel antiviral drugs to combat these diseases.

Preparation

Aurintricarboxylic acid can be prepared by the condensation of formaldehyde with salicylic acid in the presence of nitrite-containing sulfuric acid.