A gold-thiol complex with diverse biological activities
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Auranofin

Item No. 15316

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[1-(thio-κS)-β-D-glucopyranose 2,3,4,6-tetraacetato](triethylphosphine)-gold
CAS Number
34031-32-8
Synonyms
  • NSC 321521
  • Ridauragold thiol
  • SKF 39162
Molecular Formula
C20H34AuO9PS
Formula Weight
678.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 5 mg/mlEthanol: 4 mg/ml
SMILES
CC(O[C@@H]([C@@H]([C@@H](COC(C)=O)O1)OC(C)=O)[C@H]([C@@H]1[S-][Au+][P](CC)(CC)CC)OC(C)=O)=O
InChi Code
InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1
InChi Key
AUJRCFUBUPVWSZ-XTZHGVARSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $61

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    100 mg

    $109

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    500 mg

    $424

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    1 g

    $726

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    Cayman Chemical
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    Product Description

    Auranofin is a gold-thiol complex with diverse biological activities.1,2,3 It inhibits thioredoxin reductase (IC50 = 0.2 µM), increases oxidation of mitochondrial peroxiredoxin 3 (PRDX3), and induces apoptosis in Jurkat T cells.1 Auranofin reduces the production of IL-6 and activation of JAK1 and JAK2, as well as inhibits nuclear translocation of NF-kB, in primary human synoviocytes.2 It is active against P. falciparum and S. mansoni in vitro when used at concentrations ranging from 1 to 10 µM. In vivo, auranofin (2 mg/kg per day) reduces the number of peripheral blood mononuclear cells (PBMCs) containing viral DNA and delays viral rebound in macaques infected with the mac251 strain of simian immunodeficiency virus (SIV).3 Auranofin (0.5 µM) synergizes with buthionine sulfoxime (BSO) to decrease glutathione peroxidase 4 (GPX4) levels, increase intracellular accumulation of reactive oxygen species (ROS), and induce ferroptosis in Huh7 and HepG2 hepatocellular carcinoma cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cox, A.G., Brown, K.K., Arner, E.S.J., et al. The thioredoxin reductase inhibitor auranofin triggers apoptosis through a Bax/Bak-dependent process that involves peroxiredoxin 3 oxidation. Biochem. Pharmacol. 76(9), 1097-1099 (2008).

    2. Madeira, J.M., Gibson, D.L., Kean, W.F., et al. The biological activity of auranofin: Implications for novel treatment of diseases. Inflammopharmacology 20(6), 297-306 (2012).

    3. Lewis, M.G., DaFonseca, S., Chomont, N., et al. Gold drug auranofin restricts the viral reservoir in the monkey AIDS model and induces containment of viral load following ART suspension. AIDS 25(11), 1347-1356 (2011).

    4. Lippmann, J., Petri, K., Fulda, S., et al. Redox modulation and induction of ferroptosis as a new therapeutic strategy in hepatocellular carcinoma. Transl. Oncol. 13(8), 100785 (2020).

    Product Citations

    Li, Z., Ferguson, L., Deol, K.K., et al. Ribosome stalling during selenoprotein translation exposes a ferroptosis vulnerability. Nat. Chem. Biol. (2022).

    Kremer, D.M., Nelson, B.S., Lin, L., et al. GOT1 inhibition primes pancreatic cancer for ferroptosis through the autophagic release of labile iron. bioRxiv (2020).