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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 |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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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 their standard 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 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. [2]
It was found that ATA is a strong inhibitor of topoisomerases and other nucleases. It might be useful for increasing efficiency of RNA isolation. [3]
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'. [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 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. [5] [6]