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| 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 | |
3D model (JSmol) | |
| Abbreviations | ATA |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.022.390 |
| UNII | |
| |
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| Properties | |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
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.[1]
It is used to inhibitprotein biosynthesis in its initial stages. Nominally, it is used inbiological experiments as a protein inhibitor, and as anammonium salt (known asaluminon) it is used as areagent to estimate thealuminium inwater,biological tissue, andfoods.[2]
It was found that ATA is a strong inhibitor of topoisomerases and other nucleases. It might be useful for increasing efficiency ofRNA isolation.[3]
It has been discovered that using aurintricarboxylic acid againstinfluenza-A post-infection has a strong protective effect by inhibiting thevirus' ability to reproduce. In cultured caninekidney cells, it was found to reduceviral reproduction andinfection when applied post-infection, but not when used as a 'vaccine'.[4] 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.[citation needed]
Aurintricarboxylic acid and its ammonium salt shows antiviral activityin vitro againstcoronaviruses such asSARS,MERS andSARS-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.[5][6]
Aurintricarboxylic acid can be prepared by thecondensation offormaldehyde withsalicylic acid in the presence of nitrite-containing sulfuric acid.[7]
