Aurintricarboxylic acid

Last updated
Aurintricarboxylic acid [1]
Aurintricarboxylic acid.png
Aurintricarboxylic-acid-3D-balls.png
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)
AbbreviationsATA
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.022.390 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: GIXWDMTZECRIJT-UHFFFAOYSA-N Yes check.svgY
  • 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
  • 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
C22H14O9
Molar mass 422.345 g·mol−1
AppearanceDark 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.[ 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]

Preparation

Aurintricarboxylic acid can be prepared by the condensation of formaldehyde with salicylic acid in the presence of nitrite-containing sulfuric acid. [7]

Related Research Articles

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Ribonuclease L

Ribonuclease L or RNase L, known sometimes as ribonuclease 4 or 2'-5' oligoadenylate synthetase-dependent ribonuclease — is an interferon (IFN)-induced ribonuclease which, upon activation, destroys all RNA within the cell. RNase L is an enzyme that in humans is encoded by the RNASEL gene.

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Viral entry

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STAT5

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References

  1. 1 2 "Aurintricarboxylic acid". Sigma-Aldrich.
  2. "Aurintricarboxylic Acid". Reference.MD.
  3. Skidmore AF, Beebee TJ (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. doi:10.1042/bj2630073. PMC   1133392 . PMID   2481441.
  4. Hashem AM, Flaman AS, Farnsworth A, Brown EG, Van Domselaar G, He R, Li X (December 2009). "Aurintricarboxylic acid is a potent inhibitor of influenza A and B virus neuraminidases". PLOS One. 4 (12): e8350. Bibcode:2009PLoSO...4.8350H. doi:10.1371/journal.pone.0008350. PMC   2792043 . PMID   20020057.
  5. Liu C, Zhou Q, Li Y, Garner LV, Watkins SP, Carter LJ, et al. (2020). "Research and Development on Therapeutic Agents and Vaccines for COVID-19 and Related Human Coronavirus Diseases". ACS Central Science. doi: 10.1021/acscentsci.0c00272 .
  6. Morse JS, Lalonde T, Xu S, Liu WR (March 2020). "Learning from the Past: Possible Urgent Prevention and Treatment Options for Severe Acute Respiratory Infections Caused by 2019-nCoV". ChemBioChem: A European Journal of Chemical Biology. 21 (5): 730–738. doi: 10.1002/cbic.202000047 . PMID   32022370.
  7. Vogel AI. Practical Organic Chemistry Including Qualitative Organic Analysis.