Zebularine

• CAT Number: I000041
• CAS Number: 3690-10-6
• Molecular Formula: C₉H₁₂N₂O₅
• Molecular Weight: 228.20
• Purity: ≥95%
• Synonyms: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• Target: DNA Methyltransferase
• Solubility: DMSO: ≥ 45 mg/mL
• Storage: 2-8°C
• InChI: InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1
• InChIKey: RPQZTTQVRYEKCR-WCTZXXKLSA-N
• SMILES: C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

Zebularine（Cat No.:I000041）is a nucleoside analog that serves as a potent inhibitor of DNA methyltransferases, enzymes responsible for adding methyl groups to DNA, which can lead to gene silencing. By inhibiting these enzymes, zebularine reactivates silenced tumor suppressor genes and induces demethylation of genomic DNA. This compound has shown potential anti-cancer effects in various preclinical studies, particularly in solid tumors and hematological malignancies. Zebularine’s ability to modulate epigenetic modifications highlights its promise as a therapeutic agent for cancer treatment, especially in cases with aberrant DNA methylation patterns.

Reference

[1]. Zhou L, et al. Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases. J Mol Biol, 2002, 321(4), 591-599.
[2]. Lemaire M, et al. Inhibition of cytidine deaminase by zebularine enhances the antineoplastic action of 5-aza-2/’-deoxycytidine. Cancer Chemother Pharmacol, 2009, 63(3), 411-416.
[3]. Cheng JC, et al. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. J Natl Cancer Inst, 2003, 95(5), 399-409.
[4]. Cheng JC, et al. Preferential response of cancer cells to zebularine. Cancer Cell, 2004, 6(2), 151-158.