A4882

6-Thioguanine

≥98%

• Sinonimo/i: 2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
• Formula empirica (notazione di Hill): C₅H₅N₅S
• Numero CAS: 154-42-7
• Peso molecolare: 167.19
• Beilstein: 157765
• Numero CE: 205-827-2
• Numero MDL: MFCD00233553
• Codice UNSPSC: 12352202
• ID PubChem: 24890748
• NACRES: NA.77

Proprietà

• Livello qualitativo: 200
• Saggio: ≥98%
• Stato: powder
• Punto di fusione: ≥300 °C (lit.)
• Stringa SMILE: 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); WYWHKKSPHMUBEB-UHFFFAOYSA-N
• Informazioni sul gene: human ... IMPDH1(3614) , IMPDH2(3615)

Descrizione

Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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.

Informazioni sulla sicurezza

• Pittogrammi: GHS06
• Avvertenze: Danger
• Indicazioni di pericolo: H301
• Consigli di prudenza: P301 + P310
• Classi di pericolo: Acute Tox. 3 Oral
• Codice della classe di stoccaggio: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable
• Dispositivi di protezione individuale: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges