4-Deoxyuridine

CAS: 3690-10-6

Ref. 3D-ND09503

Product Information

• Name: 4-Deoxyuridine
• Synonyms: Zebularine1-b-D-Ribofuranosyl-2(1H)-pyrimidinone2-Hydroxy-1-(b-ribofuranosyl)pyrimidine, 1-(β-<span class="text-smallcaps">D</span>-Ribofuranosyl)-1,2-dihydropyrimidin-2-one, 1-(β-<span class="text-smallcaps">D</span>-Ribofuranosyl)-2-pyrimidone, 1-b-D-Ribofuranosyl-2(1H)-pyrimidinone, 1-β-<span class="text-smallcaps">D</span>-Ribofuranosyl-2(1H)-pyrimidinone, 1-β-<span class="text-smallcaps">D</span>-Ribofuranosyl-2-pyrimidinone, 2(1H)-Pyrimidinone, 1-.beta.-D-ribofuranosyl-, 2(1H)-Pyrimidinone, 1-β-<span class="text-smallcaps">D</span>-ribofuranosyl-, NSC 309132, Pyrimidin-2-one b-Ribofuranoside, Pyrimidin-2-one β-<span class="text-smallcaps">D</span>-ribofuranoside, Uridine, 4-deoxy-, Zebularine

Description

A cytidine analogue and inhibitor of DNA methyl transferases (DNMTs) with anti-cancer activity. This stable, hydrophilic compound forms covalent complexes between DNMT and zebularine-substrate DNA. It causes DNA lesions that block replication and cause replication fork collapse, leading to the formation of DNA double-strand breaks. It was also shown that zebularine-induced DNA methylation decrease in the IL-1β promoter region and disrupts molecular mechanisms of neuroinflammation. Moreover, this molecule down-regulates the DNA-methylation profile in the pluripotency genes’ promoters, which leads to improved development of somatic cell nuclear transfer (SCNT) embryos.

• Brand: Biosynth

Chemical properties

• Molecular weight: 228.21 g/mol
• Formula: C₉H₁₂N₂O₅
• Purity: Min. 95%
• Color/Form: Powder
• 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
• InChI key: InChIKey=RPQZTTQVRYEKCR-JJFBUQMESA-N
• SMILES: O=c1ncccn1[C@@H]1O[C@H](CO)[C@H](O)C1O