pyrimidin-2-one beta-ribofuranoside
ZEBULARINE
CAS: 3690-10-6
Molecular Formula: C9H12N2O5
pyrimidin-2-one beta-ribofuranoside - Names and Identifiers
| Name | ZEBULARINE |
| Synonyms | NSC309132 ZEBULARINE NSC 309132 4-DEOXYURIDINE 4-Deoxyuridine Pyrimidin-2-one -D-Ribofuranoside pyrimidin-2-one beta-ribofuranoside 1--D-Ribofuranosyl-2(1H)-pyrimidinone 1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one |
| CAS | 3690-10-6 |
| EINECS | 2017-001-1 |
| InChIKey | RPQZTTQVRYEKCR-WCTZXXKLSA-N |
pyrimidin-2-one beta-ribofuranoside - Physico-chemical Properties
| Molecular Formula | C9H12N2O5 |
| Molar Mass | 228.2 |
| Density | 1.73±0.1 g/cm3(Predicted) |
| Melting Point | 160-162?C |
| Boling Point | 499.0±55.0 °C(Predicted) |
| Water Solubility | DMSO: 16 mg/mL, soluble |
| Solubility | DMSO: 16mg/mL, soluble |
| Appearance | Morphological solid color White |
| Color | White |
| pKa | 13.48±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. |
| Use | Zebularine (NSC 309132, 4-Deoxyuridine) is a DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases and also inhibits cytidine deaminase. Ki is 2 μM in cell-free test. |
| In vitro study | Zebularine is a cytidine analog containing a 2-(1H)-pyrimidinone ring that was originally synthesized as a cytidine deaminase inhibitor. Zebularine forms a tight covalent complex with bacterial methyltransferases. Zebularine acts on N. crassa, inhibits DNA methylation, and reactivates genes silenced by methylation. Zebularine is a DNA methylation inhibitor, similar to 5-Aza-CR, rather than a selective inhibitor. Zebularine acts on T24 bladder cancer cells to reactivate the silenced p16 gene and demethylate its promoter region. Zebularine acts on T24 cells with only slight cytotoxicity. Zebularine is preferentially incorporated into the DNA of cancer cell lines and inhibits cell growth and gene expression to a greater extent than normal fibroblasts. In addition, compared to normal fibroblasts, Zebularine preferentially depletes DNA methyltransferase 1(DNMT1) of cancer cells and induces expression of cancer-associated antigen genes. |
| In vivo study | Tumor-bearing mice treated with Zebularine were slightly cytotoxic (Zebularine at a dose of 1000 mg/kg for mice with a mean maximum weight change of 11%[95% CI = 4% to 19%). Compared to control mice, mice treated with high-dose Zebularine by intraperitoneal injection or oral feeding had significantly reduced tumor volume. |
pyrimidin-2-one beta-ribofuranoside - Risk and Safety
| WGK Germany | 3 |
| RTECS | UW7539720 |
pyrimidin-2-one beta-ribofuranoside - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 4.382 ml | 21.911 ml | 43.821 ml |
| 5 mM | 0.876 ml | 4.382 ml | 8.764 ml |
| 10 mM | 0.438 ml | 2.191 ml | 4.382 ml |
| 5 mM | 0.088 ml | 0.438 ml | 0.876 ml |
Last Update：2024-01-02 23:10:35
pyrimidin-2-one beta-ribofuranoside - Reference Information
| biological activity | Zebularine (NSC 309132, 4-Deoxyuridine) is a DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases and also inhibits cytidine deaminase. Ki is 2 μM in cell-free test. |
| target | TargetValue DNA methyltransferase (Cell-free Cytidine deaminase) 2 μM(Ki) |
| Target | Value |
| DNA methyltransferase (Cell-free assay) | |
| Cytidine deaminase (Cell-free assay) | 2 μM(Ki) |
| in vitro study | Zebularine is a cytidine analog, containing 2-(1H)-pyrimidone ring, initially synthesized as a cytidine deaminase inhibitor. Zebularine forms a close covalent complex with bacterial methyltransferase. Zebularine acts on N. crassa, inhibits DNA methylation, and reactivates silencing genes caused by methylation. Zebularine is a DNA methylation inhibitor, similar to 5-Aza-CR, rather than a selective inhibitor. Zebularine acts on T24 bladder cancer cells, reactivates silenced p16 gene and demethylates its promoter region. Zebularine acts on T24 cells with only slight cytotoxicity. Compared with normal fibroblasts, Zebularine preferentially incorporate DNA into cancer cell lines and inhibit cell growth and gene expression to a greater extent. In addition, compared with normal fibroblasts, Zebularine preferentially depletes DNA methyltransferase 1(DNMT1) of cancer cells and induces the expression of cancer-related antigen genes. |
| in vivo study | Zebularine treatment of tumor-carrying mice has slight cytotoxicity (Zebularine treatment of mice at a dose of 1000 mg/kg, the average maximum weight change is 11%[95% CI = 4% to 19%). Compared with control mice, the tumor volume of mice treated with high-dose Zebularine intraperitoneal injection or oral feeding was significantly reduced. |
Last Update：2024-04-09 21:01:54
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Spot supply
Product Name: 2-Pyrimidone-1-Beta-D-Riboside Visit Supplier Webpage Request for quotationCAS: 3690-10-6
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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