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词条 Aurintricarboxylic acid
释义

  1. Preparation

  2. References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 413875357
| Reference=[1]
| 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
| 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.[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.{{cn|date=January 2013}}

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. ^{{ cite web | url = http://www.sigmaaldrich.com/catalog/product/sigma/a1895?lang=en | title = Aurintricarboxylic acid | publisher = Sigma-Aldrich }}
2. ^{{ cite web | url = http://www.reference.md/files/D001/mD001312.html | title = Aurintricarboxylic Acid | publisher = Reference.MD }}
3. ^{{ Cite journal | last1 = Skidmore | first1 = A. F. | last2 = Beebee | first2 = T. J. | 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 | doi = | pmid = 2481441 | pmc = 1133392 }}
4. ^{{ cite journal | url = http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0008350 | doi = 10.1371/journal.pone.0008350 | pmc = 2792043 | title = Aurintricarboxylic Acid is a Potent Inhibitor of Influenza A and B Virus Neuraminidases | pmid = 20020057 | year = 2009 | last1 = Hashem | first1 = A. M. | last2 = Flaman | first2 = A. S. | last3 = Farnsworth | first3 = A. | last4 = Brown | first4 = E. G. | last5 = van Domselaar | first5 = G. | last6 = He | first6 = R. | last7 = Li | first7 = X. | journal = PLoS ONE | volume = 4 | issue = 12 | pages = e8350 }}
5. ^{{ cite book | title = Practical Organic Chemistry Including Qualitative Organic Analysis | author = Arthur I. Vogel }}
{{DEFAULTSORT:Aurintricarboxylic Acid}}

4 : Triarylmethane dyes|Salicylic acids|Phenol dyes|Tricarboxylic acids

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