CAS Number154-42-7
SynonymsMFCD00233553; 2-Amino-6-methoxy purine; tabloid; 2-amino-9H-purine-6(1H)-thione; tioguanin; 2-Amino-6-purinethiol; bw5071; Tioguanine; 2-Amino-1H-purine-6(7H)-thione; 6-Thioguanine; lanvis; Tg; 6-tg; thioguanine; thio-guanin; 6-thioguanidine; EINECS 205-827-2; wellcomeu3b; 2-Amino-1,7-dihydro-6H-purine-6-thione; 6-Mercaptoguanine
Molecular FormulaC5H5N5S
Molecular Weight167.19
Purity≥98%
Density2.1±0.1 g/cm3
Boiling Point460.7±37.0 °C at 760 mmHg
Melting Point≥300 °C (lit.)
Appearancepowder
EINECS205-827-2
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 154-42-7 |
| Catalog No. | 2A-9021038 |
| Chinese Name | 硫鸟嘌呤 |
| Synonyms | MFCD00233553; 2-Amino-6-methoxy purine; tabloid; 2-amino-9H-purine-6(1H)-thione; tioguanin; 2-Amino-6-purinethiol; bw5071; Tioguanine; 2-Amino-1H-purine-6(7H)-thione; 6-Thioguanine; lanvis; Tg; 6-tg; thioguanine; thio-guanin; 6-thioguanidine; EINECS 205-827-2; wellcomeu3b; 2-Amino-1,7-dihydro-6H-purine-6-thione; 6-Mercaptoguanine |
| Molecular Formula | C5H5N5S |
| Molecular Weight | 167.19 |
| Purity | ≥98 |
| Density | 2.1±0.1 g/cm3 |
| Boiling Point | 460.7±37.0 °C at 760 mmHg |
| Melting Point | ≥300 °C (lit.) |
| Appearance | powder |
| Water Solubility | soluble |
| Storage Condition | Room temperature, sealed, dark, cool, ventilated a |
| Packaging | III |
| Application | 6-Thioguanine is an anti-leukemia and immunosuppressant, an inhibitor of SARS and MERS coronavirus papain-like protease (PLpros), and can effectively inhibit the activity of USP2 with IC50 values of |
| EINECS | 205-827-2 |
| HTC | 2933990090 |
| PubChem ID | 24890748 |
| MDL Number | MFCD00233553 |
| SMILES | NC1=Nc2nc[nH]c2C(=S)N1 |
| InChI | 1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) |
| InChI Key | WYWHKKSPHMUBEB-UHFFFAOYSA-N |
| Beilstein/REAXYS | 157765 |
| NACRES Code | NA.77 |
| UNSPSC | 12352202 |
| Hazard Symbols | 6.1 |
| MSDS | msds/21038_1_154_42_7.pdf |
| Bioactivity | 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Deubiquitinase Signaling Pathways >> Anti-infection >> SARS-CoV Research Areas >> Inflammation/Immunology Research Areas >> Cancer Research Areas >> Infection Target IC50: 25 μM (PLpros), 40 μM (Recombinant human USP2)[3] In Vitro 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-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 affects the methylation of cytosine residues by purified DNA methyltransferases including human DNMT1 and bacterial HpaII methylase. 6-Thioguanine (1 or 3 μM) decreases global cytosine methylation in Jurkat T cells and cytosine methylation in human cells at 3 μM[2]. 6-Thioguanine (18.75, 37.50, or 75.00 μM) adversely affects cell viability, but with no effect on LDH or ALT activity[3]. Cell Assay Treatments consists of 3 thiopurines (azathioprine, 6-mercaptopurine, and 6-thioguanine) at each of 6 concentrations (0.468, 0.937, 1.875, 3.750, 7.500, and 15.000 μM). Each thiopurinee is dissolved in DMSO solution to achieve a concentration of 10 mg/mL. Sterile filtered maintenance medium is used to further dilute each thiopurine solution to each of the 6 treatment concentrations. Twenty-four hours after the hepatocytes are plated on 96-well culture[3]. 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. Chemical & Physical Properties Density 2.1±0.1 g/cm3 Boiling Point 460.7±37.0 °C at 760 mmHg Melting Point ≥300 °C(lit.) Molecular Formula C5H5N5S Molecular Weight 167.192 Flash Point 232.4±26.5 °C Exact Mass 167.026566 PSA 119.28000 LogP -0.99 Vapour Pressure 0.0±1.1 mmHg at 25°C Index of Refraction 2.071 InChIKey WYWHKKSPHMUBEB-UHFFFAOYSA-N SMILES Nc1nc(=S)c2[nH]cnc2[nH]1 Water Solubility soluble |
| Use of | 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively. Properties Articles83 Name tioguanine Synonym More Synonyms 6-Thioguanine Biological Activity Description 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Deubiquitinase Signaling Pathways >> Anti-infection >> SARS-CoV Research Areas >> Inflammation/Immunology Research Areas >> Cancer Research Areas >> Infection IC50: 25 μM (PLpros), 40 μM (Recombinant human USP2)[3] In Vitro 6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-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 affects the methylation of cytosine residues by purified DNA methyltransferases including human DNMT1 and bacterial HpaII methylase. 6-Thioguanine (1 or 3 μM) decreases global cytosine methylation in Jurkat T cells and cytosine methylation in human cells at 3 μM[2]. 6-Thioguanine (18.75, 37.50, or 75.00 μM) adversely affects cell viability, but with no effect on LDH or ALT activity[3]. 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. Chemical & Physical Properties Molecular Formula C5H5N5S Exact Mass 167.026566 PSA 119.28000 LogP -0.99 Index of Refraction 2.071 InChIKey WYWHKKSPHMUBEB-UHFFFAOYSA-N SMILES Nc1nc(=S)c2[nH]cnc2[nH]1 Water Solubility soluble |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Dangerous Regulations for land transport: 2811 International Dangerous Regulations for sea transport: 2811 International Dangerous Regulations for air transport: 2811 14.2 United Nations shipping name European Land Transport Dangerous Regulations: TOXIC SOLID, ORGANIC, N.O.S. (Tioguanine) IMDG Code: TOXIC SOLID, ORGANIC, N.O.S. (Tioguanine) International air transport hazard regulations: Toxic solid, organic, n.o.s. (Tioguanine) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available The above information is believed to be correct, but is not all-inclusive and should be used as a guide only. The information in this document is based on our current knowledge and is Correct safety instructions apply to this product. This information does not represent a warranty as to the properties of this product. See reverse side of invoice or packing slip. |
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