A3656

5-Aza-2′-deoxycytidine

≥97% (HPLC), powder, DNA methyltransferase inhibitor

• Sinônimo(s): 2′-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Decitabine
• Fórmula empírica (Notação de Hill): C₈H₁₂N₄O₄
• Número CAS: 2353-33-5
• Peso molecular: 228.21
• Beilstein: 617982
• Número CE: 219-089-4
• Número MDL: MFCD00043011
• Código UNSPSC: 12352200
• ID de substância PubChem: 24890797
• NACRES: NA.77

Propriedades

• Nome do produto: 5-Aza-2′-deoxycytidine, ≥97%
• Ensaio: ≥97%
• Formulário: powder
• solubilidade: acetic acid: water (1:1): 50 mg/mL
• originador: Eisai
• cadeia de caracteres SMILES: NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2
• InChI: 1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1
• chave InChI: XAUDJQYHKZQPEU-KVQBGUIXSA-N
• Informações sobre genes: human ... DNMT1(1786) , DNMT3A(1788)

Descrição

Descrição geral

5-Aza-2′-deoxycytidine is a DNA-hypomethylating agent, which stimulates differentiation and apoptosis of leukemic cells. It is a 2′-deoxycytidine analogue. 5-Aza-2′-deoxycytidine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome and acute myeloid leukemia.

5-Aza-2′-deoxycytidine, also known as Decitabine, is a DNA-hypomethylating agent that promotes differentiation and apoptosis in leukemic cells. It is a 2′-deoxycytidine analog that causes DNA demethylation or hemi-demethylation, which can regulate gene expression by "opening" the chromatin structure, making it more sensitive to nucleases. This chromatin remodeling allows transcription factors to bind to promoter regions, facilitating the assembly of the transcription complex and subsequent gene expression. As an epigenetic modifier, Decitabine inhibits DNA methyltransferase activity, leading to DNA hypomethylation and gene activation. The reactivation of genes is further enhanced when demethylation is combined with histone hyperacetylation. Decitabine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome, and acute myeloid leukemia.

Aplicação

5-Aza-2′-deoxycytidine has been used as a demethylating agent in breast cancer cell line, chromatin, DNA and promoter region of p16 gene.

Ações bioquímicas/fisiológicas

5′-Azadeoxycytidine causes DNA demethylation or hemi-demethylation. DNA demethylation can regulate gene expression by "opening" the chromatin structure detectable as increased nuclease sensitivity. This remodeling of chromatin structure allows transcription factors to bind to the promoter regions, assembly of the transcription complex, and gene expression. Decitabine is an epigenetic modifier that inhibits DNA methyltransferase activity which results in DNA demethylation (hypomethylation) and gene activation by remodeling "opening" chromatin. Genes are synergistically reactivated when demethylation is combined with histone hyperacetylation.

Características e benefícios

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Eisai. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Nota de preparo

When prepared properly, there may be a small amount of undissolved substance.

Informações de segurança

• Pictogramas: GHS08,GHS07
• Palavra indicadora: Danger
• Frases de perigo: H302,H315,H319,H335,H341,H360
• Declarações de precaução: P202 - P261 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Classificações de perigo: Acute Tox. 4 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Órgãos-alvo: Respiratory system
• 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
• Equipamento de proteção individual: dust mask type N95 (US), Eyeshields, Gloves