A protein synthesis inhibitor with diverse biological activities
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Aurintricarboxylic Acid (ammonium salt)

Item No. 30636

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,3′-[(3-carboxy-4-oxo-2,5-cyclohexadien-1-ylidene)methylene]bis[6-hydroxy-benzoic acid, triammonium salt
CAS Number
569-58-4
Synonyms
  • ATA
Molecular Formula
C22H11O9 • 3NH4
Formula Weight
473.4
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 100 µg/ml
λmax
214 nm
SMILES
[O-]C(C(C(C=C/1)=O)=CC1=C(C2=CC=C(O)C(C([O-])=O)=C2)\C3=CC=C(O)C(C([O-])=O)=C3)=O.[NH4+].[NH4+].[NH4+]
InChi Code
InChI=1S/C22H14O9.3H3N/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);3*1H3
InChi Key
AIPNSHNRCQOTRI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

    $54

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    Cayman Chemical
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    Product Description

    Aurintricarboxylic acid (ATA) is an inhibitor of protein synthesis that has diverse biological activities.1,2,3,4,5,6,7,8 It inhibits the activity of a variety of enzymes, including the nucleases DNase I, RNase A, and S1, as well as the serine proteases trypsin and chymotrypsin in a concentration-dependent manner.2,3 ATA inhibits replication of severe acute respiratory syndrome coronavirus (SARS-CoV; EC50 = 200 µg/ml) and human enterovirus 71 in Vero cells (EV71; EC50 = 2.9 µM), as well as reduces HIV-1- or HIV-2-induced cytopathogenicity in MT-4 cells (IC50s = 1.1 and 0.85 µg/ml, respectively).4,5,6 It inhibits apoptosis induced by sanguinarine (Item No. 16951) in K562 leukemia cells when used at a concentration of 100 µM.7 ATA (20 mg/kg, i.p.) decreases CNS CD4+ T cell infiltration and reduces hind limb weakness and paralysis in a mouse model of myelin oligodendrocyte glycoprotein-induced experimental autoimmune encephalomyelitis (EAE).8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Siegelman, F., and Apirion, D. Aurintricarboxylic acid, a preferential inhibitor of initiation of protein synthesis. J. Bacteriol. 105(3), 902-907 (1971).

    2. Hallick, R.B., Chelm, B.K., Gray, P.W., et al. Use of aurintricarboxylic acid as an inhibitor of nucleases during nucleic acid isolation. Nucleic Acids Res. 4(9), 3055-3064 (1977).

    3. Bina-Stein, M., and Tritton, T.R. Aurintricarboxylic acid is a nonspecific enzyme inhibitor. Mol. Pharmacol. 12(1), 191-193 (1976).

    4. He, R., Adonov, A., Traykova-Adonova, M., et al. Potent and selective inhibition of SARS coronavirus replication by aurintricarboxylic acid. Biochem. Biophys. Res. Commun. 320(4), 1199-1203 (2004).

    5. Hung, H.-C., Chen, T.-C., Fang, M.-Y., et al. Inhibition of enterovirus 71 replication and the viral 3D polymerase by aurintricarboxylic acid. J. Antimicrob. Chemother. 65(4), 676-683 (2010).

    6. Cushman, M., Wang, P.L., Chang, S.H., et al. Preparation and anti-HIV activities of aurintricarboxylic acid fractions and analogues: Direct correlation of antiviral potency with molecular weight. J. Med. Chem. 34(1), 329-337 (1991).

    7. Hallock, S., Tang, S.-C., Buja, L.M., et al. Aurintricarboxylic acid inhibits protein synthesis independent, sanguinarine-induced apoptosis and oncosis. Toxicol. Pathol. 35(2), 300-309 (2007).

    8. Zhang, F., Wei, W., Chai, H., et al. Aurintricarboxylic acid ameliorates experimental autoimmune encephalomyelitis by blocking chemokine-mediated pathogenic cell migration and infiltration. J. Immunol. 190(3), 1017-1025 (2013).