A4882

6-Thioguanine

≥98%

• Synonym(s): 2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
• Empirical Formula (Hill Notation): C₅H₅N₅S
• CAS Number: 154-42-7
• Molecular Weight: 167.19
• Beilstein: 157765
• EC Number: 205-827-2
• MDL number: MFCD00233553
• UNSPSC Code: 12352202
• PubChem Substance ID: 24890748
• NACRES: NA.77

Properties

• Assay: ≥98%
• form: powder
• mp: ≥300 °C (lit.)
• SMILES string: 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
• Gene Information: human ... IMPDH1(3614) , IMPDH2(3615)

Description

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.

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

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.

Antimetabolite used in the treatment of leukemias. Competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase, which catalzyes a critical step in the generation of purine nucleotides.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves