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

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.

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.
Cell Data

cell lines：

Concentrations：

Incubation Time：

Powder Purity:≥99%

规格

英文别名

4-Deoxyuridine | 2(1H)-Pyrimidinone, 1-β-D-ribofuranosyl-

规格或纯度

Moligand™, 10mM in DMSO

英文名称

Zebularine (NSC 309132)

生化机理

Zebularine（NSC 309132，4-脱氧尿苷）是一种 DNA 甲基化抑制剂，能与 DNA 甲基转移酶形成共价复合物，在无细胞试验中也能抑制细胞二氨酶，_Ki值为 2 μM。

储存条件

-80℃储存

运输条件

特低温运输

名称和识别符

分子类型

小分子

Isomeric SMILES

C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

PubChem CID

100016

分子量

228.20

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高级数据

化学和物理性质

折光率

1.7

比旋光度

+156.0 ～ +160.0°(C=1, MeOH)

沸点

499.02° C

熔点

157-160° C

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批号(Lot Number)	证书类型	货号
B2306116	分析证书	Z408423

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