Auranofin

Auranofin (SKF-39162) is a thioredoxin reductase (TrxR) inhibitor with an IC50 of 0.2 μM. Auranofin exhibits antiviral activity against SARS-CoV21, with a CC50 of 4.2 μM for monkey kidney Vero E6 cells.

Product information

CAS Number: 34031-32-8

Molecular Weight: 680.50

Formula: C20H36AuO9PS

Synonym:

SKF-39162

Chemical Name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-λ⁵-phosphanyl)aurio]-λ³-sulfanyl}oxan-2-yl]methyl acetate

Smiles: CC(=O)O[C@@H]1[C@@H](COC(C)=O)O[C@@H]([SH-][Au+]P(CC)(CC)CC)[C@H](OC(C)=O)[C@H]1OC(C)=O

InChiKey: IYUHJBHUQSINCX-XTZHGVARSA-O

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 50 mg/mL (73.48 mM; Need ultrasonic).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Auranofin is a drug that is approved for the treatment of rheumatoid arthritis but is being investigated for potential therapeutic application in a number of other diseases including cancer, neurodegenerative disorders. Auranofin induces apoptosis in cells through a Bax/Bak-dependent mechanism associated with selective disruption of mitochondrial redox homeostasis in conjunction with oxidation of Prx3. Auranofin inhibits proliferation and survival of SKOV3 cells in a dose- and time-dependent manner. Auranofin treatment activates the pro-apoptotic caspase-3, increases protein levels of apoptosis-inducing proteins Bax and Bim and reduces the expression of the anti-apoptotic mediator Bcl-2 in SKOV3 cells. Auranofin is a lipophilic gold compound with anti-inflammatory and immunosuppressive properties. Auranofin inhibits the cell growth and induction of mitochondrial apoptosis in PC3 human prostate cancer cells. Treatment with auranofin significantly inhibits cell viability with an IC50 value of 2.5 μM after 24 h.

In Vivo:

Prophylactic treatment of adjuvant-induced arthritis rats with auranofin results in a slight reduction in paw edema, a complete normalization of the depressed IL-2 production, and a reduction of the elevated IL-1 production, but has no effect on the depressed IL-3 production.

References:

1. Cox AG, et al. The thioredoxin reductase inhibitor auranofin triggers apoptosis through a Bax/Bak-dependent process that involves peroxiredoxin 3 oxidation. Biochem Pharmacol. 2008 Oct 30;76(9):1097-109.
2. Park SH, et al. Auranofin displays anticancer activity against ovarian cancer cells through FOXO3 activation independent of p53. Int J Oncol. 2014 Oct;45(4):1691-8.
3. Park N, et al. Auranofin promotes mitochondrial apoptosis by inducing annexin A5 expression and translocation in human prostate cancer cells. J Toxicol Environ Health A. 2014;77(22-24):1467-76.

Products are for research use only. Not for human use.