Decitabine is a DNA methyltransferase inhibitor that integrates into DNA, causes DNA hypomethylation, and stops DNA replication in the intra-S-phase. Decitabine is used to treat myelodysplastic syndrome (MDS). Decitabine induces cell cycle arrest and apoptosis in a variety of cancer cell lines.

 

Brand: BCM

 

Target: Apoptosis; Nucleoside Antimetabolite/Analog; DNA Methyltransferase

 

Signaling Pathways: Apoptosis; Cell Cycle/Checkpoint; Chromatin/Epigenetic; DNA Damage/DNA Repair

 

In Vitro: The IC50 values of Decitabine (5AZA) for both the HL-60 and KG1a leukemic cells for 72 and 96 h exposure were approximately 100 and 10 ng/ml, respectively. At drug concentrations of 1 ng/ml, KG1a cells were more sensitive to 5AZA than TSA or depsi; HL-60 cells were more sensitive to 5AZA than TSA and more sensitive to depsi than 5AZA. Decitabine inhibited cell growth and induced G2/M arrest and apoptosis in EBVaGC cell lines. The expression of E-cadherin was up-regulated and cell motility was significantly inhibited in the cells treated with decitabine. Exposure of HeLa cells to decitabine up-regulates the expression of several pyrimidine metabolic enzymes including DCTPP1, dUTPase, dCMP deaminase, and thymidylate synthase.

 

Specific Rotation: D22 +68.5° (30 min) +57.8° (6 hr) (c = 0.5 in water)

 

Boiling Point: 370.01°C (rough estimate)

 

pKa: 14.02±0.60(Predicted)

 

Solubility: Soluble in DMSO; Soluble in Water. Insoluble in Ethanol.

 

GHS: GHS07, GHS08

 

Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC(=NC2=O)N)CO)O  

 

InChIKey: XAUDJQYHKZQPEU-KVQBGUIXSA-N  

 

InChI: 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 

 

Attribute
[Chem Name]	4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
[Synonym]	Decitabine; Deoxycytidine; Dacogen; 5-aza-2'-deoxycytidine; 5-AZA-dC; 5-aza-CdR; NSC 127716
[CAS No.]	2353-33-5
[EINECS]	219-089-4
[MDL No.]	MFCD00043011
[Formula]	C8H12N4O4
[Molecular]	228.21
[Form]	White to Off-white Powder
[Storage]	Keep in dark place. Inert atmosphere. Store in freezer, under -20°C

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