A4882

6-Thioguanine

≥98%

• Sinônimo(s): 2-Amino-6-mercaptopurine, 2-Amino-6-purinethiol
• Fórmula empírica (Notação de Hill): C₅H₅N₅S
• Número CAS: 154-42-7
• Peso molecular: 167.19
• Beilstein: 157765
• Número CE: 205-827-2
• Número MDL: MFCD00233553
• Código UNSPSC: 12352202
• ID de substância PubChem: 24890748
• NACRES: NA.77

Propriedades

• Nível de qualidade: 200
• Ensaio: ≥98%
• Formulário: powder
• pf: ≥300 °C (lit.)
• cadeia de caracteres 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)
• chave InChI: WYWHKKSPHMUBEB-UHFFFAOYSA-N
• Informações sobre genes: human ... IMPDH1(3614) , IMPDH2(3615)

Descrição

Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Informações de segurança

• Pictogramas: GHS06
• Palavra indicadora: Danger
• Frases de perigo: H301
• Declarações de precaução: P301 + P310
• Classificações de perigo: Acute Tox. 3 Oral
• Código de classe de armazenamento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges