Zebularine (NSC 309132) - Moligand™, 10mM in DMSO , CAS No.3690-10-6

CAS: 3690-10-6 Cat. No.: Z408423 Molecular Weight: 228.20 PubChem CID: 100016

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

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

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

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%

Specifications

Synonyms

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

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

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.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Isomeric SMILES: C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• PubChem CID: 100016
• Molecular Weight: 228.20

Chemical and Physical Properties

• Refractive Index: 1.7
• Specific Rotation[α]: +156.0 ～ +160.0°(C=1, MeOH)
• Boil Point(°C): 499.02° C
• Melt Point(°C): 157-160° C

References

1. Liu Xin, Li Jiale, Liu Shuyu, Long Yan, Kang Ching, Zhao Chen, Wei Ling, Huang Shaoqi, Luo Yi, Dai Bo, Zhu Xiangjia.  (2024)  Fabrication of a 3D bioprinting model for posterior capsule opacification using GelMA and PLMA hydrogel-coated resin.  Regenerative Biomaterials,      [PMID:38529352] [10.1093/rb/rbae020]