Zebularine
Zebularine (CAS 3690-10-6) is an orally bioavailable cytidine analog, functioning as a DNA methyltransferase inhibitor in mammalian cells and exhibiting inhibitory activity against DNA methylation processes in various tissues. Additionally, it can incorporate into DNA, leading to the trapping of DNA methyltransferase enzymes and inducing hypomethylation.
In experimental studies, Zebularine inhibits DNA methylation with an IC50 of 0.95 μM, tested against specific cell lines. It can also demethylate genomic DNA and reactivate silenced genes, affecting cellular epigenetic regulation.
In the context of epigenetic research and oncology, Zebularine is widely used for investigating DNA methylation mechanisms, gene expression modulation, and as a potential tool for studying cancer therapeutics.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 228.2 |
| Cas No. | 3690-10-6 |
| Formula | C9H12N2O5 |
| Synonyms | NSC309132; 4-Deoxyuridine |
| Solubility | insoluble in EtOH; ≥50.7 mg/mL in H2O; ≥8.3 mg/mL in DMSO |
| Chemical Name | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one |
| SDF | Download SDF |
| Canonical SMILES | OC[C@H]([C@H]([C@H]1O)O)O[C@H]1N(C=CC=N1)C1=O |
| 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. |
| Cell experiment [1]: | |
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Cell lines |
10T1/2 cells |
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Preparation method |
The solubility of this compound in DMSO is > 10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months. |
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Reacting condition |
30 μM; 24 hrs |
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Applications |
In 10T1/2 cells, Zebularine induced muscle cell formation. However, the 10T1/2 cells treated with Zebularine showed less muscle cell formation than those treated with either 5-Aza-CdR or 5-Aza-CR. |
| Animal experiment [1]: | |
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Animal models |
BALB/c nu/nu mice bearing EJ6 bladder cell xenografts |
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Dosage form |
500 or 1000 mg/kg; i.p. or p.o. |
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Applications |
In BALB/c nu/nu mice bearing EJ6 bladder cell xenografts, Zebularine (1000 mg/kg) significantly reduced tumor volumes when administered by intraperitoneal injection or by oral gavage. Moreover, Zebularine only showed slight cytotoxicity to tumor-bearing mice. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Cheng JC, Matsen CB, Gonzales FA, Ye W, Greer S, Marquez VE, Jones PA, Selker EU. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. J Natl Cancer Inst. 2003 Mar 5;95(5):399-409. |
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| Description | Zebularine is a potent inhibitor of both DNA Methyltransferases and cytidine deaminase. | |||||
| Targets | DNA Methyltransferases | cytidine deaminase | ||||
| IC50 | 2 μM | |||||
Quality Control & MSDS
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Chemical structure
Related Biological Data
Related Biological Data
