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100mg |
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500mg |
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1g |
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2g |
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5g |
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Purity: ≥98%
Thioguanine (6-Thioguanine; NSC752; Tabloid; 2-Amino-6-purinethiol; 6-TG), an FDA approved medication used for treating AML-acute myeloid leukemia, is an antimetabolite anticancer drug, specifically, an anti-leukemia and immunosuppressant agent. It acts by inhibiting DNMT1 activity through ubiquitin-targeted degradation.
ln Vitro |
6-Thioguanine (Thioguanine; 2-Amino-6-purinethiol) is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papin-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively[1]. 6-Thioguanine (Thioguanine) impacts the methylation of cytosine residues by purified DNA methyltransferases including human DNMT1 and bacterial HpaII methylase. 6-Thioguanine (Thioguanine) (1 or 3 μM) lowers global cytosine methylation in Jurkat T cells and cytosine methylation in human cells at 3 μM[2]. 6-Thioguanine (Thioguanine) (18.75, 37.50, or 75.00 μM) significantly impacts cell viability, but with no effect on LDH or ALT activity[3].
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ln Vivo |
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Animal Protocol |
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References |
[1]. Chuang SJ, et al. 6-Thioguanine is a noncompetitive and slow binding inhibitor of human deubiquitinating protease USP2. Sci Rep. 2018 Feb 15;8(1):3102.
[2]. Wang H, et al. 6-Thioguanine perturbs cytosine methylation at the CpG dinucleotide site by DNA methyltransferases in vitro and acts as a DNA demethylating agent in vivo. Biochemistry. 2009 Mar 17;48(10):2290-9. [3]. LaDuke KE, et al. Effects of azathioprine, 6-mercaptopurine, and 6-thioguanine on canine primary hepatocytes. Am J Vet Res. 2015 Jul;76(7):649-55 |
Molecular Formula |
C5H5N5S
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Molecular Weight |
167.1917
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CAS # |
154-42-7
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Appearance |
Typically exists as solids (or liquids in special cases) at room temperature
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SMILES |
S=C1NC(N)=NC2=C1NC=N2
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InChi Key |
WYWHKKSPHMUBEB-UHFFFAOYSA-N
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InChi Code |
InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
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Chemical Name |
2-amino-1H-purine-6(7H)-thione
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Synonyms |
2-Amino-6-purinethiol; thioguanine; ThioguanineTabloid; Tioguanine. Lanvis; Tioguanin; 6TG; TG. BW 5071; WR1141; X 27.
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
DMSO : ~10 mg/mL (~59.81 mM)
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.67 mg/mL (9.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 5.9812 mL | 29.9061 mL | 59.8122 mL | |
5 mM | 1.1962 mL | 5.9812 mL | 11.9624 mL | |
10 mM | 0.5981 mL | 2.9906 mL | 5.9812 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
NCT00002944 | Completed | Drug: carboplatin Drug: lomustine |
Brain Tumors Central Nervous System Tumors |
Children's Oncology Group | April 1997 | Phase 3 |
NCT02912676 | Completed | Drug: Thioguanine (oral) | Acute Lymphoblastic Leukemia | Kjeld Schmiegelow | October 2016 | Phase 1 Phase 2 |
NCT00587873 | Completed | Drug: Leucovorin calcium Drug: 6-Thioguanine |
Hodgkin's Disease | Memorial Sloan Kettering Cancer Center |
March 1994 | Phase 2 |
NCT05276284 | Recruiting | Combination Product: Atezolizumab, 6-mercaptopurine, 6-thioguanine |
Solid Tumor, Adult Metastatic Cancer |
Kristoffer Rohrberg | September 1, 2022 | Phase 1 Phase 2 |
Time-dependent inactivation of USP2 by 6TG. (A) Different concentrations of 6TG (0 μM, closed circles; 10–100 μM, open circles) were incubated with USP2 and enzyme activity was measured for 200 s. Across all trials, Ub-AFC concentration was held at 0.5 μM and USP2 concentration was held at 0.2 μM. The solid lines show the best fit results when the data was fitted to the slow-binding equation. (B) The observed inactivation rate constants (kinact) from panel A were replotted against 6TG concentrations. The solid line represents the best fit of the data to the saturation equation. The apparent Kinact value is shown in Table 1. td> |
Comparison with other structures of human USP2. Overlay of the active site of human USP2-Ub complex (grey; PDB code: 2hd5) with that of USP2-Ub-6TG complex (USP2: cyan; Ub: yellow; 6TG: orange) (A) or that of USP2 C276S mutant (green) in complex with Ub (magenta) (B). The dashed lines show hydrophilic interactions. The arrow in panel (A) indicates the movement of residue Asp575, while that in panel (B) shows the side-chain movement of residue 276, which has been mutated from cysteine to serine. td> |
6-Thioguanine treatment results in decreased cytosine methylation in human cells. Plotted are the percentages of global cytosine methylation in genomic DNA isolated from Jurkat T cells that were untreated or treated with SG or 5-aza-dC. The data represent the means and standard deviations of results from three independent drug treatments and HPLC measurements. The P values were calculated by using paired t-test. td> |