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Azacitidine

Azacitidine

Product ID A9602
Cas No. 320-67-2
Purity ≥98%
Product Unit SizeCostQuantityStock
100 mg $59.50 In stock
250 mg $139.00 In stock
1 g $459.60 In stock
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  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
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Description

Azacytidine is a cytidine analog that is incorporated into DNA, inhibiting DNA methyltransferase (DNMT) activity and preventing DNA repair. This demethylating agent is clinically used to treat myelodysplastic syndromes and potentiates the effects of other chemotherapeutics, such as cisplatin. Azacytidine exhibits anticancer chemotherapeutic, immunomodulatory, and antiviral activities. In vitro, azacytidine increases levels of Bax and Bcl-2 in astrocytoma cells, and induces differentiation of mesenchymal stem cells into cardiomyocytes. In vivo, azacytidine increases glial differentiation and decreases cell proliferation, inhibiting tumor growth of glioma xenografts. Additionally, azacytidine decreases cell growth and inhibits tumor xenografts of myelodysplastic cells. In leukoblasts, this compound upregulates the expression of tumor antigens, and in vivo, it increases the number of Treg and CD8+ T cells. Azacytidine also inhibits replication of HIV in cellular models without displaying cytotoxicity.

Product Info

Cas No.

320-67-2

Purity

≥98%

Formula

C8H12N4O5

Formula Wt.

244.20

Chemical Name

4-amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one

IUPAC Name

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

Synonym

4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin, 5-azacytidine.

Melting Point

226-232°C

Solubility

Soluble in water, but unstable.

Appearance

White or almost white crystalline powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

A9602 MSDS PDF

Info Sheet

A9602 Info Sheet PDF

Brochures

Epigenetic Modifiers Booklet

References

Borodovsky A, Salmasi V, Turcan S, et al. 5-azacytidine reduces methylation, promotes differentiation and induces tumor regression in a patient-derived IDH1 mutant glioma xenograft. Oncotarget. 2013 Oct;4(10):1737-47. PMID: 24077805.

Solís-Paredes M, Eguía-Aguilar P, Chico-Ponce de León F, et al. Epigenetic modifications in cell lines of human astrocytoma differentially regulate expression of apoptotic genes. Childs Nerv Syst. 2013 Aug 13. Epub ahead of print. PMID: 23943192.

Tsujioka T, Yokoi A, Uesugi M, et al. Effects of DNA methyltransferase inhibitors (DNMTIs) on MDS-derived cell lines. Exp Hematol. 2013 Feb;41(2):189-97. PMID: 23085465.

Kimura S, Kuramoto K, Homan J, et al. Antiproliferative and antitumor effects of azacitidine against the human myelodysplastic syndrome cell line SKM-1. Anticancer Res. 2012 Mar;32(3):795-8. PMID: 22399596.

Goodyear OC, Dennis M, Jilani NY, et al. Azacitidine augments expansion of regulatory T cells after allogeneic stem cell transplantation in patients with acute myeloid leukemia (AML). Blood. 2012 Apr 5;119(14):3361-9. PMID: 22234690.

Ye NS, Chen J, Luo GA, et al. Proteomic profiling of rat bone marrow mesenchymal stem cells induced by 5-azacytidine. Stem Cells Dev. 2006 Oct;15(5):665-76. PMID: 17105402.

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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