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5-Aza-2′-deoxycytidine

5-Aza-2′-deoxycytidine

Product ID A9603
Cas No. 2353-33-5
Purity ≥98%
Product Unit SizeCostQuantityStock
5 mg $75.30 In stock
10 mg $142.90 In stock
50 mg $602.20 In stock
Bulk Quote

Quicklinks

  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

Decitabine is a deoxycytidine analog that is incorporated into DNA, inhibiting DNA methyltransferase (DNMT1/3A/3B) activity. This demethylating agent is clinically used to treat myelodysplastic syndromes. Decitabine’s inhibition of DNA methyltransferase may be modulated by PKC. Decitabine exhibits anticancer chemotherapeutic, immunomodulatory, and neurotoxic activities. In cellular models of acute myelogenous leukemia (ALL), decitabine demethylation prevents cancer cell inactivation of TRAIL signaling, increasing apoptosis and cell death. In vivo, decitabine stimulates increases in cancer testis antigen-specific cytotoxic (CD8+) T cell activity. In dopaminergic neurons, this compound induces apoptosis and upregulation of tyrosine hydroxylase and α-synuclein, suggesting complications for use in subjects with Parkinson’s disease. Decitabine also inhibits replication of HIV in cellular models without displaying cytotoxicity. Additionally, this compound shows benefit in the treatment of sickle-cell anemia through its stimulation of fetal hemoglobin production.

Product Info

Cas No.

2353-33-5

Purity

≥98%

Formula

C8H12N4O4

Formula Wt.

228.21

IUPAC Name

4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3, 5-triazin-2-one

Synonym

2'-Deoxy-5-azacytidine, 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Decitabine

Solubility

acetic acid: water (1:1): 50 mg/mL

Appearance

White to off white powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

A9603 MSDS PDF

Info Sheet

A9603 Info Sheet PDF

References

Zhou JH, Yao YS, Wang LX, et al. Demethylating agent decitabine induces autologous cancer testis antigen specific cytotoxic T lymphocytes in vivo. Chin Med J (Engl). 2013 Dec;126(23):4552-6. PMID: 24286424.

Wang Y, Wang X, Li R, et al. A DNA methyltransferase inhibitor, 5-aza-2'-deoxycytidine, exacerbates neurotoxicity and upregulates Parkinson's disease-related genes in dopaminergic neurons. CNS Neurosci Ther. 2013 Mar;19(3):183-90. PMID: 23441691.

Soncini M, Santoro F, Gutierrez A, et al. The DNA demethylating agent decitabine activates the TRAIL pathway and induces apoptosis in acute myeloid leukemia. Biochim Biophys Acta. 2013 Jan;1832(1):114-20. PMID: 23046813.

Datta J, Ghoshal K, Motiwala T, et al. Novel Insights into the Molecular Mechanism of Action of DNA Hypomethylating Agents: Role of Protein Kinase C δ in Decitabine-Induced Degradation of DNA Methyltransferase 1. Genes Cancer. 2012 Jan;3(1):71-81. PMID: 22893792.

Saba HI. Decitabine in the treatment of myelodysplastic syndromes. Ther Clin Risk Manag. 2007 Oct;3(5):807-17. PMID: 18473005.

Momparler RL. Pharmacology of 5-Aza-2'-deoxycytidine (decitabine). Semin Hematol. 2005 Jul;42(3 Suppl 2):S9-16. PMID: 16015507.

Bouchard J, Walker MC, Leclerc JM, et al. 5-azacytidine and 5-azadeoxycytidine inhibit human immunodeficiency virus type 1 replication in vitro. Antimicrob Agents Chemother. 1990 Feb;34(2):206-9. PMID: 1691617.

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