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    Zebularine (NSC309132; 4-Deoxyuridine)
    Zebularine (NSC309132; 4-Deoxyuridine)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V0407
    CAS #: 3690-10-6Purity ≥98%

    Description: Zebularine (formerly 4-Deoxyuridine; NSC-309132) is a selective and potent inhibitor of DNA methylation/methyltransferase with anticancer activity. It inhibits DNA methylation by forming a covalent complex with DNA methyltransferases. zebularine is a stable cytidine analog that also inhibits cytidinedeaminase with a Ki of 2 μM in a cell-free assay.  

    References:J Mol Biol. 2002 Aug 23;321(4):591-9; Cancer Chemother Pharmacol. 2009 Feb;63(3):411-6.

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    Molecular Weight (MW)228.2
    FormulaC9H12N2O5
    CAS No.3690-10-6
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 46 mg/mL (201.6 mM)
    Water: 46 mg/mL (201.6 mM)
    Ethanol:<1 mg/mL
    Solubility (In vivo)Saline: 30 mg/mL
    SynonymsZebularine; NSC-309132; NSC 309132; NSC309132; 4-Deoxyuridine; 4 Deoxyuridine


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    In Vitro

    In vitro activity: Zebularine is a cytidine analogue containing a 2-(1H)-pyrimidinone ring, originally synthesized as a cytidine deaminase inhibitor. Zebularine is shown to form a tight, covalent complex with bacterial methyltransferases. 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. 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.


    Cell Assay: For methylation analysis, 10T1/2 cells and T24 cells are treated with the various concentrations of zebularine. For 10T1/2 cells, the medium is changed 24 hours after the initial drug treatment, whereas for T24 cells, the medium is changed 24 hours or 48 hours after the initial drug treatment. DNA and RNA are harvested from 10T1/2 cells 72 hours after initial drug treatment and from T24 cells 96 hours after initial drug treatment. The methylation status of the indicated DNA regions is measured in two separate and independent experiments, both of which are done in duplicate.

    In VivoZebularine 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.
    Animal model Male BALB/c nu/nu mice
    Formulation & Dosage Dissolved in 0.45% saline; 500 mg/kg, 1000 mg/kg; i.p. and p.o.
    ReferencesFASEB J. 2000 Nov;14(14):2339-44; Cancer Res. 2010 Aug 1;70(15):6268-76.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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