A3656

5-Aza-2′-deoxycytidine

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

• 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/REAXYS Number: 617982
• EC Number: 219-089-4
• MDL number: MFCD00043011
• UNSPSC Code: 12352200
• PubChem Substance ID: 24890797
• NACRES: NA.77

Properties

• Product Name: 5-Aza-2′-deoxycytidine, ≥97%
• 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.[1] It is a 2′-deoxycytidine analogue.[2] 5-Aza-2′-deoxycytidine is used to treat chronic myelomonocytic leukemia, refractory anemia, myelodysplastic syndrome and acute myeloid leukemia.[1][2]

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.

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.[3][4][5][6]

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.

Preparation Note

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

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H315,H319,H335,H341,H360
• pcodes: P202 - P261 - P301 + P312 - 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: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Gloves