Aurintricarboxylic acid
| Skeletal formula of aurintricarboxylic acid | |
| Ball-and-stick model of the aurintricarboxylic acid molecule | |
| Names | |
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| IUPAC name
5,5'-((3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene)bis(2-hydroxybenzoic acid)
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| Other names
Aluminon free acid
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| Identifiers | |
4431-00-9  |
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| Abbreviations | ATA |
| ChEBI | CHEBI:87397 |
| ChEMBL | ChEMBL275938 |
| ChemSpider | 2172 323088 (tautomeric form) |
| Jmol 3D model | Interactive image Interactive image |
| PubChem | 2259 |
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| Properties | |
| C22H14O9 | |
| Molar mass | 422.35 g·mol−1 |
| Appearance | Dark red to brown powder |
| Melting point | 300 °C (572 °F; 573 K) |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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.[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]
Preparation
Aurintricarboxylic acid can be prepared by the condensation of formaldehyde with salicylic acid in the presence of nitrite-containing sulfuric acid.[5]
References
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