Aurintricarboxylic acid

Aurintricarboxylic acid^[1]

Names
IUPAC name 5,5'-((3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene)bis(2-hydroxybenzoic acid)
Other names Aluminon free acid
Identifiers
CAS Number	4431-00-9
3D model (Jmol)	Interactive image Interactive image
Abbreviations	ATA
ChEBI	CHEBI:87397
ChEMBL	ChEMBL275938
ChemSpider	2172 323088 (tautomeric form)
ECHA InfoCard	100.022.390
PubChem	2259
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) Key: GIXWDMTZECRIJT-UHFFFAOYSA-N 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	422.35 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).
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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.

Preparation

Aurintricarboxylic acid can be prepared by the condensation of formaldehyde with salicylic acid in the presence of nitrite-containing sulfuric acid.^[5]

References

1. "Aurintricarboxylic acid". Sigma-Aldrich.
2. "Aurintricarboxylic Acid". Reference.MD.
3. Skidmore, A. F.; Beebee, T. J. (October 1989). "Characterization and use of the potent ribonuclease inhibitor aurintricarboxylic acid for the isolation of RNA from animal tissues". The Biochemical Journal. 263 (1): 73–80. PMC 1133392. PMID 2481441.
4. Hashem, A. M.; Flaman, A. S.; Farnsworth, A.; Brown, E. G.; van Domselaar, G.; He, R.; Li, X. (2009). "Aurintricarboxylic Acid is a Potent Inhibitor of Influenza A and B Virus Neuraminidases". PLoS ONE. 4 (12): e8350. doi:10.1371/journal.pone.0008350. PMC 2792043. PMID 20020057.
5. Arthur I. Vogel. Practical Organic Chemistry Including Qualitative Organic Analysis.