6-Thioguanine
SIGMA/A4882 - ≥98%
Synonym: 2-
CAS Number: 154-42-7
Empirical Formula (Hill Notation): C5H5N5S
Molecular Weight: 167.19
EC Number: 205-827-2
MDL Number: MFCD00233553
Linear Formula: C5H5N5S
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A4882-100MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A4882-1G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A4882-250MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A4882-500MG
| assay | ≥98% |
| biological source | synthetic (organic) |
| form | powder |
| InChI | 1S/C5H5N5S/c6-5-9-3-2(4(1 |
| InChI key | WYWHKKSPHMUBEB-UHFFFAOYSA |
| mp | ≥300 °C (lit.) |
| Quality Level | 200  |
| SMILES string | NC1=Nc2nc[nH]c2C(=S)N1 |
| solubility | 1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow |
| storage temp. | room temp |
| Application: | 6-Thioguanine has been used: • to induce autophagy and apoptosis in colorectal cancer cell lines HCT116 • as a selection marker in the mutation and survival assay in chinese hamster lung fibroblasts culture V79 • as a selection marker in clonogenic Lung metastasis assay of 4T1-luc cells |
| Biochem/physiol Actions: | Antimetabolite used in the treatment of leukemias. Competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase |
| Biochem/physiol Actions: | Ribosylated and phosphorylated by the same pathway as natural purine bases; as the nucleotide, inhibits a variety of cellular processes involved in nucleic acid synthesis. Has a long history as an effective treatment of leukemia. |
| General description: | 6-Thioguanine is a variant of guanine with hydrogen bonding at the N-7 of the purine ring. Its association with cytosine alters the dimension of the base stacking. 6-Thioguanine usage in treating inflammatory bowel disease (IBD) contributes to nodular regenerative hyperplasia (NRH) in the liver. |
| Packaging: | 1, 5 g in glass bottle |
| Packaging: | 100, 250, 500 mg in glass bottle |
| Symbol |  GHS06 |
| Signal word | Danger |
| Hazard statements | H301 |
| Precautionary statements | P301 + P310 |
| Hazard Codes | T |
| Risk Statements | 25 |
| Safety Statements | 28-36/37/39-45 |
| RIDADR | UN 2811 6.1 / PGIII |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% |
| mp | ≥300 °C (lit.) |
| Storage Temp. | room temp |
| UNSPSC | 12352202 |