[CAS NO. 3690-10-6] Zebularine (NSC 309132)

Name: Zebularine (NSC 309132)
Brand: Arctom Scientific
SKU: SLK-S7113

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PRODUCTS SPECIFICATIONS [3690-10-6]

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Catalog

SLK-S7113

Brand

Selleck

CAS

3690-10-6

DESCRIPTION [3690-10-6]

Overview

MDL	MFCD04973699
Molecular Weight	228.2
Molecular Formula	C9H12N2O5
SMILES	O[C@H]1[C@@](O[C@H](CO)[C@H]1O)(N2C(=O)N=CC=C2)[H]

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume 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
50 mM	0.0876 mL	0.4382 mL	0.8764 mL

Description

Zebularine (NSC 309132, 4-Deoxyuridine) is a inhibitor that forms a covalent complex with , also inhibits cytidinedeaminase with 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. 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.

References

[1] Zhou L, et al. J Mol Biol, 2002, 321(4), 591-599.
[2] Lemaire M, et al. Cancer Chemother Pharmacol, 2009, 63(3), 411-416.
[3] Cheng JC, et al. J Natl Cancer Inst, 2003, 95(5), 399-409.
[4] Cheng JC, et al. Cancer Cell, 2004, 6(2), 151-158.

Synonyms

2(1H)-Pyrimidinone, 1-β-D-ribofuranosyl-

1-β-D-Ribofuranosyl-2(1H)-pyrimidinone

4-Deoxyuridine

1-(β-D-Ribofuranosyl)-2-pyrimidone

Uridine, 4-deoxy-

Pyrimidin-2-one β-D-ribofuranoside

1-β-D-Ribofuranosyl-2-pyrimidinone

Zebularine

NSC 309132

1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one