6-THIOGUANINE (C005B-019917)

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.

Molecular Weight: 167.19. Empirical Formula: C₅H₅N₅S. Quality Level: 200. 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). 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: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges.