A3656

5-Aza-2′-deoxycytidine

≥97%

• Synonym(s): 2′-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Decitabine
• Empirical Formula (Hill Notation): C₈H₁₂N₄O₄
• CAS Number: 2353-33-5
• Molecular Weight: 228.21
• Beilstein: 617982
• EC Number: 219-089-4
• MDL number: MFCD00043011
• PubChem Substance ID: 24890797
• NACRES: NA.77

Properties

• Quality Level: 200
• Assay: ≥97%
• form: powder
• solubility: acetic acid: water (1:1): 50 mg/mL
• originator: Eisai
• SMILES string: 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
• InChI key: XAUDJQYHKZQPEU-KVQBGUIXSA-N
• Gene Information: human ... DNMT1(1786) , DNMT3A(1788)

Description

General description

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.

Application

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

Biochem/physiol Actions

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.

Features and Benefits

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.

Safety Information

• Pictograms: GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H302 - H315 - H319 - H335 - H341 - H360
• Precautionary Statements: P201 - P301 + P312 + P330 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves