Auranofin

Manufactured by Enzo Life Sciences

Sourced in Israel

Auranofin is a gold-containing compound used as a laboratory reagent. It functions as an inhibitor of certain enzymes and proteins.

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Lab products found in correlation

19 protocols using auranofin

Auranofin, Pyrimethamine, and Sulfadiazine Evaluation

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Auranofin (Enzo Life Sciences), was dissolved in 100% ethanol as a stock solution (4 mg/mL) and then diluted in complete tissue culture medium (DMEM +2% FBS) for final concentrations of 0.1 to 19 µM. For in vivo experiments, the Auranofin concentration used was 1 mg/kg of estimated body weight.
Pyrimethamine (Sigma Aldrich) was dissolved in 100% ethanol in a stock concentration of 5 mg/mL. Three final dilutions in complete tissue culture medium were examined: 0.02, 0.1 and 0.2 µM. Sulfadiazine (Sigma Aldrich) was dissolved in complete medium at a final stock concentration of 5 mg/mL. Three doses in complete medium were evaluated: 0.2, 1 and 2 µM. Testing of Pyrimethamine/Sulfadiazine combinations by checkerboard method (using abovementioned concentrations) was carried out in triplicates and in three independent experiments.

Andrade R.M., Chaparro J.D., Capparelli E, & Reed S.L. (2014). Auranofin Is Highly Efficacious against Toxoplasma gondii In Vitro and in an In Vivo Experimental Model of Acute Toxoplasmosis. PLoS Neglected Tropical Diseases, 8(7), e2973.

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Auranofin Inhibits α-Synuclein Aggregation

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Auranofin (Enzo Life Sciences, Shoham, Israel), triethylphosphine (2,3,4,6-tetra-O-acetyl-β-1-d-thiopyranosato-S) gold(I); LDEE from TEVA Ltd Israel. SD, SDA, and TXM-peptide TXM-CB3, and AD4 (NAC-amide), were custom synthesized by Novetide, Ltd, Haifa, Israel. All other materials were purchased from Sigma, Jerusalem. α-syn plasmid was a kind gift of Dr. R. Sharon (Hadassah Ein Kerem, Jerusalem).

Wiesen T, & Atlas D. (2022). Novel anti-apoptotic L-DOPA precursors SuperDopa and SuperDopamide as potential neuroprotective agents for halting/delaying progression of Parkinson’s disease. Cell Death & Disease, 13(3), 227.

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Antifungal Susceptibility Assay

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Fungal strains used in this study are presented in Table 1. Yeast peptone dextrose agar (YPD) was purchased from BD Biosciences (San Jose, CA). Auranofin (Enzo Life Sciences, Farmingdale, NY), fluconazole (Acros Organics, New Jersey), and flucytosine (TCI chemicals, Tokyo, Japan) were purchased from commercial vendors. XTT-sodium salt, menadione, RPMI powder, and MOPS were purchased from Sigma-Aldrich (St. Louis, MO). Concanavalin A–conjugated with FITC 488 dye was acquired from Thermo Fisher Scientific Inc. (Waltham, MA).

Thangamani S., Maland M., Mohammad H., Pascuzzi P.E., Avramova L., Koehler C.M., Hazbun T.R, & Seleem M.N. (2017). Repurposing Approach Identifies Auranofin with Broad Spectrum Antifungal Activity That Targets Mia40-Erv1 Pathway. Frontiers in Cellular and Infection Microbiology, 7, 4.

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Auranofin Derivatives Preparation

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Auranofin (Enzo Life Sciences), aurothioglucose, aurothiomalate, and triethyl phosphine (Sigma Aldrich) were dissolved in 100% DMSO as a stock solution (5 mg/mL) and then diluted in D10 for final concentrations of 0.156–40 µM (in twofold increments). Derivatives of Auranofin were provided by the Barrios laboratory (University of Utah) and synthesized as previously described (24 (link)). Stock solutions were prepared in DMSO and diluted in D10 for final concentrations ranging from 0.156–320 µM (in twofold increments).

Ma C.I., Tirtorahardjo J.A., Schweizer S.S., Zhang J., Fang Z., Xing L., Xu M., Herman D.A., Kleinman M.T., McCullough B.S., Barrios A.M, & Andrade R.M. (2024). Gold(I) ion and the phosphine ligand are necessary for the anti-Toxoplasma gondii activity of auranofin. Microbiology Spectrum, 12(2), e02968-23.

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Modulating Cellular Redox Balance

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Cells were treated with 5Z-7-oxozeaenol (TAK1 inhibitor) (Cat. no. O9890, Sigma-Aldrich, St. Louis, MO). A stock solution of Z-7-oxozeaenol inhibitor in DMSO was added to achieve a final concentration of 5 µM in media. DMSO (0.1%) was used as the vehicle control in all cases. Injectable N-acetylcysteine (NAC) (Acetadote, Cumberland Pharmaceuticals, Nashville, TN) was added 1 h following treatment with TAK1 inhibitor to achieve a final concentration of 10 mM. Buthionine sulfoximine (BSO) dissolved in PBS (Sigma-Aldrich, St. Louis, MO) was added 8 h prior to the addition of TAK1 inhibitor to a final concentration of 100 µM. Cells were treated with auranofin dissolved in absolute ethanol (Enzo Life Sciences, Farmingdale, NY) 3 h prior to treatment with TAK1 inhibitor to achieve a final concentration of 500 nM (0.1% ethanol). Treatments were added directly to the complete media specific for each cell line.

Hrabe J.E., O’Leary B.R., Fath M.A., Rodman S.N., Button A.M., Domann F.E., Spitz D.R, & Mezhir J.J. (2015). Disruption of thioredoxin metabolism enhances the toxicity of transforming growth factor β-activated kinase 1 (TAK1) inhibition in KRAS-mutated colon cancer cells. Redox Biology, 5, 319-327.

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Bacterial Strain Culturing Protocols

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Bacterial strains used in this study are presented in Tables 1 and 2. Mueller-Hinton broth (MHB) was purchased from Sigma-Aldrich while Trypticase soy broth (TSB), Trypticase soy agar (TSA), and mannitol salt agar (MSA) were purchased from Becton, Dickinson and Company (Cockeysville, MD). Auranofin (Enzo Life Sciences), vancomycin hydrochloride (Gold Biotechnology) and linezolid (Selleck Chemicals) were all purchased from commercial vendors.

Thangamani S., Mohammad H., Abushahba M.F., Sobreira T.J., Hedrick V.E., Paul L.N, & Seleem M.N. (2016). Antibacterial activity and mechanism of action of auranofin against multi-drug resistant bacterial pathogens. Scientific Reports, 6, 22571.

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Auranofin and Thioredoxin Mimetic Peptides

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All materials were purchased from Sigma, Jerusalem, if not otherwise stated; Auranofin (Enzo life sciences, Shoham, Israel), triethylphosphine (2,3,4,6-tetra-O-acetyl-β-1-d-thiopyranosato-S) gold(I); thioredoxin mimetic (TXM) peptides TXM-CB3 and -CB4 were custom synthesized by Novetide, Ltd. Haifa; Thinkpeptides, Oxford, UK, and GL Biochem., Shanghai, China; tissue culture serum and medium were from Biological Industries, Kibbutz Beit-Haemek, Israel.

Cohen-Kutner M., Khomsky L., Trus M., Ben-Yehuda H., Lenhard J.M., Liang Y., Martin T, & Atlas D. (2014). Thioredoxin-mimetic peptide CB3 lowers MAPKinase activity in the Zucker rat brain. Redox Biology, 2, 447-456.

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Synthesis and Characterization of Gold(I) Complexes

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The following gold(I) complexes were purchased: Auranofin – 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-galacotopyranosato)(ethylphosphine) gold(I) (Enzo Life Sciences, Cat No BML-EI206); Aurothioglucose (brand name: Solganal) – 3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-thiolate gold (I) (Millipore Sigma, Cat No A0606); Aurothiomalate (brand name: Myochrysine) – (1,2-Dicarboxyethylthio) disodium salt hydrate gold(I) (Millipore Sigma, Cat No 157201); 4 – (Tri-n-ethylphosphine)gold(I) chloride (Millipore Sigma, Cat No 288225); 10 – (Tri-n-methylphosphine)gold(I) chloride (Strem Chemicals, Cat No 79–0850); 17 – (Tri-tert-butylphosphine)gold(I) chloride (Strem Chemicals, Cat No 79–0740); 19 – (Methyldiphenylphosphine)gold(I) chloride (Millipore Sigma, Cat No 717290); 20 – (Triphenylphosphine)gold(I) chloride (Millipore Sigma, Cat No 254037); 21 – [Tri(p-tolyl)phosphine]gold(I) chloride (Millipore Sigma, Cat No 717282); and 22 – [Tris(para-trifluoromethylphenyl)phosphine]gold(I) chloride (Millipore Sigma, Cat No 665177).

Miyamoto Y., Aggarwal S., Celaje J.J., Ihara S., Ang J., Eremin D.B., Land K.M., Wrischnik L.A., Zhang L., Fokin V.V, & Eckmann L. (2021). Gold(I) phosphine derivatives with improved selectivity as topically active drug leads to overcome 5-nitroheterocyclic drug resistance in Trichomonas vaginalis. Journal of medicinal chemistry, 64(10), 6608-6620.

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Auranofin-based Enzyme Assay Protocol

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Auranofin was obtain from Enzo Life Sciences. CDNB (1‐chloro‐2,4‐dinitro‐benzene) was obtained from Milipore‐SIGMA, Oakville, Canada. Amplex Ultrared was obtained from THERMO‐FISHER, Waltham, MA. All other chemicals and enzymes were purchased from Milipore‐SIGMA or ACROS, Geel, Belgium.

Munro D., Baldy C., Pamenter M.E, & Treberg J.R. (2019). The exceptional longevity of the naked mole‐rat may be explained by mitochondrial antioxidant defenses. Aging Cell, 18(3), e12916.

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Auranofin and Thioredoxin Mimetic Assay

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Auranofin, triethylphosphine (2,3,4,6-tetra-O-acetyl-β-1-d-thiopyranosato-S) gold(I) (Enzo Life Sciences, Shoham, Israel); AD4 (NAC-amide) and thioredoxin mimetic peptides (TXM) TXM-CB3, were custom synthesized by Novetide, Ltd., Haifa, Israel; TXB-CB13(DY70) was from Biotech and Pharma Ltd, Israel. Tissue culture serum and medium were from Biological Industries, Kibbutz Beit-Haemek, Israel. All materials were purchased from Sigma, Jerusalem, if not otherwise stated.

Baratz-Goldstein R., Deselms H., Heim L.R., Khomski L., Hoffer B.J., Atlas D, & Pick C.G. (2016). Thioredoxin-Mimetic-Peptides Protect Cognitive Function after Mild Traumatic Brain Injury (mTBI). PLoS ONE, 11(6), e0157064.

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