Zebularine (NSC 309132)

Catalog No.S7113 Synonyms: 4-Deoxyuridine

For research use only.

Zebularine (NSC 309132, 4-Deoxyuridine) is a DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases, also inhibits cytidinedeaminase with Ki of 2 μM in a cell-free assay.

Zebularine (NSC 309132) Chemical Structure

CAS No. 3690-10-6

Selleck's Zebularine (NSC 309132) has been cited by 8 Publications

1 Customer Review

Purity & Quality Control

Choose Selective DNA Methyltransferase Inhibitors

Biological Activity

Description Zebularine (NSC 309132, 4-Deoxyuridine) is a DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases, also inhibits cytidinedeaminase with Ki of 2 μM in a cell-free assay.
Features Very stable with half-life of ~44 h at 37°C in PBS at pH 1.0 and approx. 508 h at pH 7.
Targets
DNA methyltransferase [1]
(Cell-free assay)
Cytidine deaminase [2]
(Cell-free assay)
2 μM(Ki)
In vitro

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

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
human T24 cells NEjUWoRHfW6ldHnvckBie3OjeR?= M{nrTlExOCEQvF2= Mnm1PEBl[Xm| M{TkbWlv\HWldHnvckBw\iCyMU[g[4Vv\SCneIDy[ZN{cW:wIHnuJIh2dWGwIGSyOEBk\WyuczDheEAyODBidV2gZYZ1\XJiODDkZZl{KGK7IILlZYwhfGmvZTDQR3IhcW5icILld4Vv[2Vib3[gNVAxKG2PIITofY1q\GmwZR?= NUXqeo1nOTlyME[zPFI>
human HCT15 cells NELN[41HfW6ldHnvckBie3OjeR?= MkXENVAxKM7:TR?= M3vFSVgh\GG7cx?= MonoTY5lfWO2aX;uJI9nKHBzNjDn[Y5mKGW6cILld5Nqd25iaX6gbJVu[W5iSFPUNVUh[2WubIOgZZQhOTByIIXNJIFnfGW{IEig[IF6eyCkeTDy[YFtKHSrbXWgVGNTKGmwIIDy[ZNmdmOnIH;mJFExOCCvTTD0bJlucWSrbnW= NXfwXWx6OTlyME[zPFI>
Assay
Methods Test Index PMID
Western blot DNMT1 / DNMT3a / DNMT3b ; CDK2 / p-Rb / Rb ; MeCP2 / MBD2 / MBD3 / Acetyl-H3 / Acetyl-H4 23320119 19459041
Growth inhibition assay Cell viability 19459041
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]

Protocol (from reference)

Animal Research:[3]
  • Animal Models: male BALB/c nu/nu mice
  • Dosages: 500 mg/kg, 1000 mg/kg
  • Administration: Intraperitoneal, oral

Solubility (25°C)

In vitro

DMSO 46 mg/mL
(201.57 mM)
Water 46 mg/mL
(201.57 mM)
Ethanol Insoluble

In vivo

Add solvents to the product individually and in order
(Data is from Selleck tests instead of citations):
Saline
For best results, use promptly after mixing.

30 mg/mL

Chemical Information

Molecular Weight 228.2
Formula

C9H12N2O5

CAS No. 3690-10-6
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O

In vivo Formulation Calculator (Clear solution)

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Molarity Calculator

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Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

Handling Instructions

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