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- 2',3',5'-triacetyl-5-Azacytidine
2',3',5'-triacetyl-5-Azacytidine
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.
| Physical Appearance | A crystalline solid |
| Storage | Store at -20°C |
| M.Wt | 370.3 |
| Cas No. | 10302-78-0 |
| Formula | C14H18N4O8 |
| Solubility | ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide |
| Chemical Name | 4-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one |
| SDF | Download SDF |
| Canonical SMILES | O=C1N([C@@H]2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]2OC(C)=O)C=NC(N)=N1 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Chemical structure
