Zebularine


CAS No. : 3690-10-6

Zebularine,3690-10-6
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:I000041
Synonyms:1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Molecular Formula:C₉H₁₂N₂O₅
Molecular Weight:228.2
Target:DNA Methyltransferase
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Assay:≥98%
Appearance:A crystalline solid
Cat No:I000041
Cas No:3690-10-6
Product-Name:Zebularine
MDL No:MFCD04973699
InChI:InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1
InChIKey:RPQZTTQVRYEKCR-WCTZXXKLSA-N
SMILES:C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O

Zebularine(NSC309132; 4-Deoxyuridine) is a DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases, also inhibits cytidinedeaminase with Ki of 2 μM.
IC50 value:
Target: DNA methyltransferase
in vitro: Zebularine is shown to form a tight, covalent complex with bacterial methyltransferases [1]. Zebularine is a cytidine analogue containing a 2-(1H)-pyrimidinone ring, originally synthesized as a cytidine deaminase inhibitor [2]. In N. crassa, zebularine inhibits DNA methylation and reactivates a gene previously silenced by methylation. Zebularine is a global inhibitor of DNA methylation, similar to 5-Aza-CR, rather than a selective inhibitor. Zebularine induces the myogenic phenotype in 10T1/2 cells, which is a phenomenon unique to DNA methylation inhibitors. Zebularine reactivates a silenced p16 gene and demethylates its promoter region in T24 bladder carcinoma cells. Zebularine is only slightly cytotoxic to T24 cells [3]. Zebularine is preferentially incorporated into DNA and exhibits greater cell growth inhibition and gene expression in cancer cell lines compared to normal fibroblasts. In addition, zebularine preferentially depletes DNA methyltransferase 1 (DNMT1) and induces expression of cancer-related antigen genes in cancer cells relative to normal fibroblasts [4].
in vivo: Zebularine is only slightly cytotoxic to tumor-bearing mice (average maximal weight change in mice treated with 1000 mg/kg zebularine = 11% [95% CI = 4% to 19%]). Compared with those in control mice, tumor volumes are statistically significantly reduced in mice treated with high-dose zebularine administered by intraperitoneal injection or by oral gavage [3].


[1]. Zhou L, et al. Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases. J Mol Biol, 2002, 321(4), 591-599.
[2]. Lemaire M, et al. Inhibition of cytidine deaminase by zebularine enhances the antineoplastic action of 5-aza-2/'-deoxycytidine. Cancer Chemother Pharmacol, 2009, 63(3), 411-416.
[3]. Cheng JC, et al. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. J Natl Cancer Inst, 2003, 95(5), 399-409.
[4]. Cheng JC, et al. Preferential response of cancer cells to zebularine. Cancer Cell, 2004, 6(2), 151-158.

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