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Description: DNA methyltransferase and cytidine deaminase inhibitor
Alternative Names: NSC 309132
Chemical Name: 1-β-D-Ribofuranosyl-2(1H)-pyrimidinone
Purity: ≥99% (HPLC)
Biological Activity for Zebularine
Zebularine is an orally active DNA methyltransferase inhibitor. Inhibits tumor cell proliferation (IC50 = 120 μM) and re-activates silenced genes in T24 bladder carcinoma cells. Inhibits cytidine deaminase (Ki ~ 2 μM); induces differentiation of mesenchymal stem cells into cardiomyocytes.
Technical Data for Zebularine
| M. Wt | 228.2 |
| Formula | C9H12N2O5 |
| Storage | Desiccate at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 3690-10-6 |
| PubChem ID | 100016 |
| InChI Key | RPQZTTQVRYEKCR-WCTZXXKLSA-N |
| Smiles | O[C@@H]1[C@@H](CO)O[C@@H](N2C(N=CC=C2)=O)[C@@H]1O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Zebularine
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 22.82 | 100 | |
| DMSO | 22.82 | 100 |
Preparing Stock Solutions for Zebularine
The following data is based on the product molecular weight 228.2. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 4.38 mL | 21.91 mL | 43.82 mL |
| 5 mM | 0.88 mL | 4.38 mL | 8.76 mL |
| 10 mM | 0.44 mL | 2.19 mL | 4.38 mL |
| 50 mM | 0.09 mL | 0.44 mL | 0.88 mL |
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Product Datasheets for Zebularine
References for Zebularine
References are publications that support the biological activity of the product.
Laliberte et al (1992) Potent inhibitors for the deamination of cytosine arabinoside and 5-aza-2'-deoxycytidine by human cytidine deaminase. Cancer Chemother.Pharmacol. 30 7 PMID: 1375134
Ben-Kasus et al (2005) Metabolic activation of zebularine, a novel DNA methylation inhibitor, in human bladder carcinoma cells. Biochem.Pharmacol. 70 121 PMID: 15885659
Naeem et al (2012) DNA methylation inhibitors, 5-azacytidine and zebularine potentiate the trans-differentiation of rat bone marrow mesenchymal stem cells into cardiomyocytes. Cardiovasc.Ther. [Epub ahead of print]
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Keywords: Zebularine, Zebularine supplier, DNA, methyltransferase, inhibitors, inhibits, Transferases, cytidine, deaminases, NSC309132, dnmt, cardiomyocyte, differentiation, mesenchymal, stem, cells, epigenetics, NSC, 309132, Methyltransferases, Deaminases, Cardiomyocyte, Stem, Cells, Mesenchymal, 2293, Tocris Bioscience
4 Citations for Zebularine
Citations are publications that use Tocris products. Selected citations for Zebularine include:
Zou et al (2019) The DNA Methylation Inhibitor Zebularine Controls CD4+ T Cell Mediated Intraocular Inflammation. Front Immunol 10 1950 PMID: 31475011
Biergans et al (2012) DNA methylation mediates the discriminatory power of associative long-term memory in honeybees. PLoS One 7 e39349 PMID: 22724000
Trowbridge et al (2012) Haploinsufficiency of Dnmt1 impairs leukemia stem cell function through derepression of bivalent chromatin domains. Gastroenterology 26 344 PMID: 22345515
Soltoff and Lannon (2013) Activation of ERK1/2 by store-operated calcium entry in rat parotid acinar cells. PLoS One 8 e72881 PMID: 24009711
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Cell Cycle and DNA Damage Research Product Guide
This product guide provides a review of the cell cycle and DNA damage research area and lists over 150 products, including research tools for:
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Epigenetics in Cancer Research Product Guide
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Epigenetics Scientific Review
Written by Susanne Müller-Knapp and Peter J. Brown, this review gives an overview of the development of chemical probes for epigenetic targets, as well as the impact of these tool compounds being made available to the scientific community. In addition, their biological effects are also discussed. Epigenetic compounds available from Tocris are listed.