:Aurintricarboxylic acid

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 413875357

| Reference={{ cite web | url = http://www.sigmaaldrich.com/catalog/product/sigma/a1895?lang=en | title = Aurintricarboxylic acid | publisher = Sigma-Aldrich }}

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = Aurintricarboxylic acid.png

| ImageAlt = Skeletal formula of aurintricarboxylic acid

| ImageFile1 = Aurintricarboxylic-acid-3D-balls.png

| ImageAlt1 = Ball-and-stick model of the aurintricarboxylic acid molecule

| PIN=3,3′-[(3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(6-hydroxybenzoic acid)

| OtherNames=5,5′-[(3-Carboxy-4-oxocyclohexa-2,5-dien-1-ylidene)methylene]bis(2-hydroxybenzoic acid)
Aluminon free acid

|Section1={{Chembox Identifiers

| Abbreviations = ATA

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2172

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 87397

| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID1 = 323088

| ChemSpiderID1_Comment = (tautomeric form)

| 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)

| InChIKey = GIXWDMTZECRIJT-UHFFFAOYAI

| SMILES1 = 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

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 275938

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GIXWDMTZECRIJT-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=4431-00-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = NP9O8E29QW

| PubChem=2259

| 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

}}

|Section2={{Chembox Properties

| C=22 | H=14 | O=9

| Appearance=Dark red to brown powder

| Density=

| MeltingPtC=300

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

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.{{ cite web | url = http://www.reference.md/files/D001/mD001312.html | title = Aurintricarboxylic Acid | publisher = Reference.MD }}

It was found that ATA is a strong inhibitor of topoisomerases and other nucleases. It might be useful for increasing efficiency of RNA isolation.{{cite journal | vauthors = Skidmore AF, Beebee TJ | title = Characterization and use of the potent ribonuclease inhibitor aurintricarboxylic acid for the isolation of RNA from animal tissues | journal = The Biochemical Journal | volume = 263 | issue = 1 | pages = 73–80 | date = October 1989 | pmid = 2481441 | pmc = 1133392 | doi = 10.1042/bj2630073 }}

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'.{{cite journal | vauthors = Hashem AM, Flaman AS, Farnsworth A, Brown EG, Van Domselaar G, He R, Li X | title = Aurintricarboxylic acid is a potent inhibitor of influenza A and B virus neuraminidases | journal = PLOS ONE | volume = 4 | issue = 12 | pages = e8350 | date = December 2009 | pmid = 20020057 | pmc = 2792043 | doi = 10.1371/journal.pone.0008350 | bibcode = 2009PLoSO...4.8350H | doi-access = free }} 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|date=January 2013}}

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.{{cite journal | vauthors = Liu C, Zhou Q, Li Y, Garner LV, Watkins SP, Carter LJ, Smoot J, Gregg AC, Daniels AD, Jervey S, Albaiu D | display-authors = 6 | title = Research and Development on Therapeutic Agents and Vaccines for COVID-19 and Related Human Coronavirus Diseases | journal = ACS Central Science | date = 2020 | volume = 6 | issue = 3 | pages = 315–331 | doi = 10.1021/acscentsci.0c00272 | pmid = 32226821 | pmc = 7094090 | doi-access = free }}{{cite journal | vauthors = Morse JS, Lalonde T, Xu S, Liu WR | title = Learning from the Past: Possible Urgent Prevention and Treatment Options for Severe Acute Respiratory Infections Caused by 2019-nCoV | journal = ChemBioChem | volume = 21 | issue = 5 | pages = 730–738 | date = March 2020 | pmid = 32022370 | doi = 10.1002/cbic.202000047 | pmc = 7162020 | doi-access = free }}