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Zebularine DNA methylation inhibitor

Catalog No.A1915
Size Price Stock Qty
10mM (in 1mL DMSO)
$55.00
In stock
10mg
$70.00
In stock
50mg
$280.00
In stock

Tel: +1-832-696-8203

Email: [email protected]

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Sample solution is provided at 25 µL, 10mM.

Product Citations

1. Griffin PT, Niederhuth CE, Schmitz RJ. "A Comparative Analysis of 5-Azacytidine- and Zebularine-Induced DNA Demethylation." G3 (Bethesda). 2016 Sep 8;6(9):2773-80. PMID:27402357

Quality Control

Chemical structure

Zebularine

Related Biological Data

Zebularine

Related Biological Data

Zebularine

Biological Activity

Description Zebularine is a potent inhibitor of both DNA Methyltransferases and cytidine deaminase.
Targets DNA Methyltransferases cytidine deaminase        
IC50   2 μM        

Protocol

Cell experiment [1]:

Cell lines

10T1/2 cells

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.

Reacting condition

30 μM; 24 hrs

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]:

Animal models

BALB/c nu/nu mice bearing EJ6 bladder cell xenografts

Dosage form

500 or 1000 mg/kg; i.p. or p.o.

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.

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.

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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Chemical Properties

Cas No. 3690-10-6 SDF Download SDF
Synonyms NSC 309132
Chemical Name 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Canonical SMILES C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O
Formula C9H12N2O5 M.Wt 228.2
Solubility ≥50.7mg/ml in H2O,>8.3mg/mL in DMSO Storage Store at -20°C
Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Background

Zebularine, a chemically stable cytidine analog containing a 2-(1H)-pyridimidinone ring, is an effective DNA methylation inhibitor which can act with DNA methyltransferases to form a covalent complex. It has been shown to cause demethylation and reactivation of a silenced and hypermethylated p16 gene. Zebularine is able to induce the myogenic phenotype in 10T1/2 cells, which is a phenomenon unique to DNA methylation inhibitors. zebularine can act as a pro-drug leading to inhibition of DNA methylation and gene activation in fungal and mammalian cells. It was the only slightly cytotoxic to T24 cells in vitro. Zebularine is stable in aqueous solution up to a pH of 12.

Reference

C.B. Yoo, J.C. Cheng and P.A. Jones. Zebularine: a new drug for epigenetic therapy. Biochemical Society Transactions. 2004; 32(6): 910 – 912.

Jonathan C. Cheng, Cindy B. Matsen, Felicidad A. Gonzales, Wei Ye, Sheldon Greer, Victor E. Marquez, Peter A. Jones, Eric U. Selker. Inhibition of DNA Methylation and Reactivation of Silenced Genes by Zebularine. Journal of the National Cancer Institute. 2003; 95(5): 399 – 409.