CAS 154-42-7|6-Thioguanine
Introduction：Basic information about CAS 154-42-7|6-Thioguanine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | 6-Thioguanine | ||
|---|---|---|---|
| CAS Number | 154-42-7 | Molecular Weight | 167.192 |
| Density | 2.1±0.1 g/cm3 | Boiling Point | 460.7±37.0 °C at 760 mmHg |
| Molecular Formula | C5H5N5S | Melting Point | ≥300 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 232.4±26.5 °C |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | tioguanine |
|---|---|
| Synonym | More Synonyms |
6-Thioguanine BiologicalActivity
| 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 >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>DeubiquitinaseSignaling Pathways >>Anti-infection >>SARS-CoVResearch Areas >>Inflammation/ImmunologyResearch Areas >>CancerResearch 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- Standard Draize test
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Human
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 160 mg/kg
- TOXIC EFFECTS :
- Gastrointestinal - other changes Blood - hemorrhage Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 54 mg/kg
- TOXIC EFFECTS :
- Gastrointestinal - other changes Blood - hemorrhage Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- LD10 - Lethal Dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1600 mg/kg
- TOXIC EFFECTS :
- Blood - changes in bone marrow (not otherwise specified)
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 23720 ug/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - conjunctive irritation Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 55990 ug/kg/5D-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 56 mg/kg/2W-I
- TOXIC EFFECTS :
- Blood - normocytic anemia Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 650 mg/kg/26W-I
- TOXIC EFFECTS :
- Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 46500 ug/kg/5D-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 19950 ug/kg/4D-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 23700 ug/kg/13D-I
- TOXIC EFFECTS :
- Gastrointestinal - ulceration or bleeding from large intestine Nutritional and Gross Metabolic - body temperature increase Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 5700 ug/kg/13D-I
- TOXIC EFFECTS :
- Gastrointestinal - ulceration or bleeding from large intestine Nutritional and Gross Metabolic - body temperature increase Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 25 mg/kg
- SEX/DURATION :
- female 12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 10 mg/kg
- SEX/DURATION :
- female 7 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- TYPE OF TEST :
- Cytogenetic analysis
MUTATION DATA - TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 15 ug/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 139,149,1984 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5676 No. of Facilities: 18 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 82 (estimated) No. of Female Employees: 27 (estimated)
- TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 15 ug/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 139,149,1984 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5676 No. of Facilities: 18 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 82 (estimated) No. of Female Employees: 27 (estimated)
Safety Information
| Symbol | GHS06 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H301 |
| Precautionary Statements | P301 + P310 |
| Personal Protective Equipment | Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges |
| Hazard Codes | T:Toxic; |
| Risk Phrases | R25 |
| Safety Phrases | S28-S36/37/39-S45-S28A |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | UP0740000 |
| Packaging Group | III |
| Hazard Class | 6.1 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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Synonyms
| MFCD00233553 |
| 2-Amino-6-methoxy purine |
| tabloid |
| 2-aminomercaptopurine |
| 2-amino-9H-purine-6(1H)-thione |
| tioguanin |
| 2-Amino-6-purinethiol |
| bw5071 |
| Tioguanine |
| 2-Amino-6-mercaptopurine,2-Amino-6-purinethiol |
| 7H-Purine-6-thiol, 2-amino- |
| 2-Amino-6-mercaptopurine |
| 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 |
