1. Epigenetics
    Autophagy
  2. DNA Methyltransferase
    Autophagy

Zebularine (Synonyms: NSC309132; 4-Deoxyuridine)

Cat. No.: HY-13420 Purity: 99.92%
Handling Instructions

Zebularine (NSC309132; 4-Deoxyuridine) is a DNA methyltransferase inhibitor; also an inhibitor of cytidine deaminase with a Ki of 0.95 μM.

For research use only. We do not sell to patients.

Zebularine Chemical Structure

Zebularine Chemical Structure

CAS No. : 3690-10-6

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10 mM * 1 mL in DMSO USD 86 In-stock
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Estimated Time of Arrival: December 31
10 mg USD 78 In-stock
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50 mg USD 330 In-stock
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  • Protocol

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  • References

Description

Zebularine (NSC309132; 4-Deoxyuridine) is a DNA methyltransferase inhibitor; also an inhibitor of cytidine deaminase with a Ki of 0.95 μM.

IC50 & Target[1][4]

DNMT1

 

DNMT3a/3L

 

Cytidine deaminase

0.95 μM (Ki)

Autophagy

 

In Vitro

Zebularine exerts its demethylation activity by stabilizing the binding of DNMTs to DNA, hindering the methylation and decreasing the dissociation, thereby trapping the enzyme and preventing turnover even at other sites. zebularine enhances tumor cell chemo- and radiosensitivity and has antimitogenic and angiostatic activities[1]. Zebularine inhibits DNA methylation and reactivates a gene previously silenced by methylation. 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 demethylated its promoter region in T24 bladder carcinoma cells[2]. Zebularine treatment inhibits cell growth in a dose and time dependent manner with an IC50 of ∼100 μM and 150 μM in MDA-MB-231 and MCF-7 cells, respectively, on 96 h exposure. At high doses zebularine induced changes in apoptotic proteins in a cell line specific manner manifested by alteration in caspase-3, Bax, Bcl2 and PARP cleavage[3]. Zebularine is also a potent competitive inhibitor of the enzyme CR deaminase. The Ki for zebularine is 0.95μM[4].

In Vivo

Zebularine is only slightly cytotoxic to tumor-bearing mice. 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[2]. Zebularine also enhances the survival time of mice with L1210 leukemia treated with 5-AZA-CdR. About 27% of the mice treated with this drug combination has a survival time longer than the mice treated with only 5-AZA-CdR[4].

Solvent & Solubility
In Vitro: 

DMSO : ≥ 29 mg/mL (127.08 mM)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 4.3821 mL 21.9106 mL 43.8212 mL
5 mM 0.8764 mL 4.3821 mL 8.7642 mL
10 mM 0.4382 mL 2.1911 mL 4.3821 mL
*Please refer to the solubility information to select the appropriate solvent.
References
Cell Assay
[2]

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[2].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Administration
[2]

EJ6 cells (5 × 105/injection) suspended in PBS are inoculated subcutaneously into the right and left flanks (along the midaxillary lines) of 4- to 6-week-old male BALB/c nu/nu mice. Mice (n=30) are randomLy divided into six groups (intraperitoneal control, oral control, intraperitoneal zebularine at 500 mg/kg, oral zebularine at 500 mg/kg, intraperitoneal zebularine at 1000 mg/kg, and oral zebularine at 1000 mg/kg). Each group consisted of five mice (at least six tumors per group; one or two mice per group are randomLy killed at earlier time points to establish a time course of expression). After 2–3 weeks and after macroscopic tumors (50–200 mm3) had formed, zebularine or control treatments are initiated. Zebularine, at doses of 500 mg/kg or 1000 mg/kg, is administered daily by intraperitoneal injection or oral gavage in a solution of 0.45% saline over a period of 18 days[2].

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

References
Molecular Weight

228.2

Formula

C₉H₁₂N₂O₅

CAS No.

3690-10-6

SMILES

O=C1N=CC=CN1[[email protected]]2[[email protected]@H]([[email protected]@H]([[email protected]@H](CO)O2)O)O

Storage
Powder -20°C 3 years
  4°C 2 years
In solvent -80°C 6 months
  -20°C 1 month
Shipping

Room temperature in continental US; may vary elsewhere

Purity: 99.92%

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Product Name:
Zebularine
Cat. No.:
HY-13420
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Zebularine

Cat. No.: HY-13420