A4882

6-Thioguanin

≥98%

• Synonym(e): 2-Amino-6-mercapto-purin, 2-Amino-6-purinthiol
• Empirische Formel (Hill-System): C₅H₅N₅S
• CAS-Nummer: 154-42-7
• Molekulargewicht: 167.19
• Beilstein: 157765
• EG-Nummer: 205-827-2
• MDL-Nummer: MFCD00233553
• UNSPSC-Code: 12352202
• PubChem Substanz-ID: 24890748
• NACRES: NA.77

Eigenschaften

• Qualitätsniveau: 200
• Assay: ≥98%
• Form: powder
• mp (Schmelzpunkt): ≥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)
• InChIKey: WYWHKKSPHMUBEB-UHFFFAOYSA-N
• Angaben zum Gen: human ... IMPDH1(3614) , IMPDH2(3615)

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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.

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H301
• P-Sätze: P301 + P310
• Gefahreneinstufungen: Acute Tox. 3 Oral
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges