A4882

6-Thioguanine

≥98%, Guanine antimetabolite, powder

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

Properties

• Product Name: 6-Thioguanine, ≥98%
• InChI key: WYWHKKSPHMUBEB-UHFFFAOYSA-N
• InChI: 1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
• SMILES string: NC1=Nc2nc[nH]c2C(=S)N1
• biological source: synthetic (organic)
• assay: ≥98%
• form: powder
• mp: ≥300 °C (lit.)
• solubility: 1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow
• storage temp.: room temp
• Quality Level: 200
• Gene Information: human ... IMPDH1(3614), IMPDH2(3615)

Description

Application

6-Thioguanine has been used:

• to induce autophagy and apoptosis in colorectal cancer cell lines HCT116[1]
• as a selection marker in the mutation and survival assay in chinese hamster lung fibroblasts culture V79[2]
• as a selection marker in clonogenic Lung metastasis assay of 4T1-luc cells[3]

Biochem/physiol Actions

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.

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.[4] 6-Thioguanine usage in treating inflammatory bowel disease (IBD) contributes to nodular regenerative hyperplasia (NRH) in the liver.[5]

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 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
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges