A4882

6-Thioguanine

≥98%

• Synonyme(s) : 2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
• Formule empirique (notation de Hill): C₅H₅N₅S
• Numéro CAS: 154-42-7
• Poids moléculaire : 167.19
• Beilstein: 157765
• Numéro CE : 205-827-2
• Numéro MDL: MFCD00233553
• Code UNSPSC : 12352202
• ID de substance PubChem : 24890748
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 200
• Essai: ≥98%
• Forme: powder
• Pf: ≥300 °C (lit.)
• Chaîne SMILES: 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)
• Clé InChI: WYWHKKSPHMUBEB-UHFFFAOYSA-N
• Informations sur le gène: human ... IMPDH1(3614) , IMPDH2(3615)

Description

Description générale

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

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Pictogrammes: GHS06
• Mention d'avertissement: Danger
• Mentions de danger: H301
• Conseils de prudence: P301 + P310
• Classification des risques: Acute Tox. 3 Oral
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges