Zebularine

Pricing Availability Delivery Time Qty
Cat.No. 2293 - Zebularine | C9H12N2O5 | CAS No. 3690-10-6
Description: DNA methyltransferase and cytidine deaminase inhibitor
Alternative Names: NSC 309132
Chemical Name: 1-β-D-Ribofuranosyl-2(1H)-pyrimidinone
Purity: ≥99% (HPLC)
Datasheet
Citations (3)
Literature

Biological Activity

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.

Compound Libraries

Zebularine is also offered as part of the Tocriscreen Epigenetics Toolbox and Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.

Technical Data

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 22.82 100
water 22.82 100

Preparing Stock Solutions

The following data is based on the product molecular weight 228.2. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
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

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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] PMID:


If you know of a relevant reference for Zebularine, please let us know.

View Related Products by Product Action

View all DNA Methyltransferase Inhibitors

Keywords: DNA methyltransferase inhibitors inhibits Transferases cytidine deaminases NSC309132 dnmt cardiomyocyte differentiation mesenchymal stem cells epigenetics NSC 309132 DNA Methyltransferases

3 Citations for Zebularine

Citations are publications that use Tocris products. Selected citations for Zebularine include:

Soltoff and Lannon (2013) Activation of ERK1/2 by store-operated calcium entry in rat parotid acinar cells. PLoS One 8 e72881 PMID: 24009711

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


Do you know of a great paper that uses Zebularine from Tocris? If so please let us know.

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Reviews

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Epigenetics

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.

Epigenetics

Epigenetics Research Bulletin

Produced by Tocris and updated in 2014, the epigenetics research bulletin gives an introduction into mechanisms of epigenetic regulation, and highlights key Tocris products for epigenetics targets including:

  • Bromodomains
  • DNA Methyltransferases
  • Histone Deacetylases
  • Histone Demethylases
  • Histone Methyltransferases

Pathways for Zebularine

Protocols

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