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2',3',5'-triacetyl-5-Azacytidine
prodrug form of 5-azacytidine, a DNA methyltransferase inhibitor

Catalog No.C4119
Size Price Stock Qty
5mg
$54.00
In stock
10mg
$102.00
In stock
50mg
$431.00
In stock
100mg
$755.00
In stock

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Sample solution is provided at 25 µL, 10mM.

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Quality Control & MSDS

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Chemical structure

2

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Chemical Properties

Cas No. 10302-78-0 SDF Download SDF
Chemical Name 4-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
Canonical SMILES O=C1N([[email protected]@H]2O[[email protected]](COC(C)=O)[[email protected]@H](OC(C)=O)[[email protected]]2OC(C)=O)C=NC(N)=N1
Formula C14H18N4O8 M.Wt 370.3
Solubility Soluble in DMSO Storage Store at -20°C
Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Background

2',3',5'-triacetyl-5-Azacytidine (TAC) is the lead prodrug form of 5-azacytidine which may be rapidly absorbed after oral administration [1]. 5-Azacytidine is an inhibitor of DNA methyltransferase [2].

The DNA methyltransferase belongs to a family of enzymes involved in catalyzing the transfer of a methyl group to DNA. DNA methylation has been implicated in regulating gene expression in normal and malignant cells [2].

In vivo: In CD-1 mice, oral administration of TAC for five days per week for 2 weeks didn’t result in animal deaths and weight loss, but induced changes in hematological parameters, lymph nodes, bone marrow, and duodenal epithelium. TAC inhibited global DNA methylation in the spleen and gut. In an in vivo L1210 leukemia model, TAC exhibited antineoplastic activity [1].

References:
[1] Ziemba A, Ramirez M C, Freeman B, et al.  Abstract# 3369: Development of oral demethylating agents for the treatment of myelodysplastic syndrome[J]. 2009.
[2] Brueckner B, Boy R G, Siedlecki P, et al.  Epigenetic reactivation of tumor suppressor genes by a novel small-molecule inhibitor of human DNA methyltransferases[J]. Cancer research, 2005, 65(14): 6305-6311.