Zebularine An inhibitor of DNA methyltransferase (Dnmt)

Zebularine (CAS 3690-10-6)

Zebularine | CAS 3690-10-6 is rated 5.0 out of 5 by 1.
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Synonym: 4-Deoxyuridine; 1-b-D-Ribofuranosyl-2(1H)-pyrimidinone; 1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one, 2-Pyrimidone-1-β-D-riboside
Application: An inhibitor of DNA methyltransferase (Dnmt)
CAS Number: 3690-10-6
Purity: ≥98%
Molecular Weight: 228.21
Molecular Formula: C9H12N2O5
* Refer to Certificate of Analysis for lot specific data (including water content).
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Zebularine is a cell-permeable chemically stable cytidine analog and DNA methylation inhibitor which acts by forming a covalent complex with DNMT. It displays antiangiogenic activity and markedly inhibits vessel formation in different tumor models. It reactivates silenced E-cadherin and potentiates the effects of other epigenetic therapeutics such as vorinistat. Induces differentiation of mesenchymal cells into cardiomyocytes. Inhibits cytidine deaminase (CDD).


References

1. Frick, L., et al., 1989. Binding of pyrimidin-2-one ribonucleoside by cytidine deaminase as the transition-state analogue 3,4-dihydrouridine and the contribution of the 4-hydroxyl group to its binding affinity. Biochemistry. 28(24): 9423-30. PMID: 2692708
2. Zhou, L., et al., 2002. Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases. Journal of molecular biology. 321(4): 591-9. PMID: 12206775
3. Cheng, Jonathan C., et al., 2003. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. Journal of the National Cancer Institute. 95(5): 399-409. PMID: 12618505
4. Cheng, Jonathan C., et al., 2004. Preferential response of cancer cells to zebularine. Cancer cell. 6(2): 151-8. PMID: 15324698

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in DMSO (>25 mg/ml), methanol (5 mg/ml), water (>25 mg/ml), DMF (~5 mg/ml), and ethanol (~0.25 mg/ml).
Storage :
Store at 4° C
Melting Point :
157-160° C
Boiling Point :
499.02° C at 760 mmHg (Predicted)
Density :
1.73 g/cm3 (Predicted)
Refractive Index :
n20D 1.70 (Predicted)
Optical Activity :
α20/D +163.4°, c = 0.47 in methanol
IC50 :
Tumor cell proliferation: IC50 = 120 µM
Ki Data :
CDD: Ki= ~2 µM
pK Values :
pKa: 13.48 (Predicted), 1.79 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UW7539720
PubChem CID :
328839
MDL Number :
MFCD04973699
Beilstein Registry :
751056
SMILES :
C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O

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Zebularine  Product Citations

See how others have used Zebularine. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 15550378  Peng, B. et al. 2005. J. Biol. Chem. 280: 4182-4187.

PMID: # 14729971  Cheng, J.C. et al. 2004. Mol. Cell. Biol. 24: 1270-1278.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from A noticeable decrease in Dnmt1 protein expression A noticeable decrease in Dnmt1 protein expression was observed by WB in HeLa cells post treatment with Zebularine. -SCBT QC
Date published: 2015-05-15
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