CAS 3690-10-6

Zebularine

Description:

Zebularine, with the CAS number 3690-10-6, is a nucleoside analog that has garnered interest in the field of epigenetics and cancer research. It is structurally related to cytidine, featuring a unique modification that enhances its stability and bioavailability. Zebularine is known for its ability to inhibit DNA methyltransferases, enzymes responsible for adding methyl groups to DNA, which can lead to gene silencing. This property makes it a valuable tool for studying gene expression and potential therapeutic applications in cancer treatment, where abnormal methylation patterns are often observed. Zebularine is typically administered in vitro and has shown promise in reactivating silenced genes, thereby restoring normal cellular functions. Additionally, it has been investigated for its effects on cell proliferation and differentiation. However, its use in clinical settings is still under exploration, and further studies are needed to fully understand its pharmacological properties and potential side effects. Overall, zebularine represents a significant compound in the ongoing research into epigenetic modulation and its implications for disease treatment.

Formula: C₉H₁₂N₂O₅

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-WCTZXXKLSA-N

SMILES: O[C@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C(=O)N=CC=C2

Synonyms:

• 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-
• 4-Deoxyuridine
• NSC 309132
• Pyrimidin-2-one b-Ribofuranoside
• Pyrimidin-2-one β-<span class="text-smallcaps">D</span>-ribofuranoside
• Uridine, 4-deoxy-
• Zebularine
• 1-(β-D-Ribofuranosyl)-2-pyrimidone
• 1-(beta-D-Ribofuranosyl)pyrimidin-2(1H)-one

Zebularine

CAS: 3690-10-6

Formula: C₉H₁₂N₂O₅

Purity: >98.0%(HPLC)(T)

Color and Shape: White to Light yellow powder to crystal

Molecular weight: 228.20

Ref: 3B-Z0022

4-Deoxyuridine

CAS: 3690-10-6

Formula: C₉H₁₂N₂O₅

Molecular weight: 228.20

Ref: 7W-GN2416

Zebularine

CAS: 3690-10-6

Zebularine

Formula: C₉H₁₂N₂O₅

Purity: 99.5%

Color and Shape: Solid

Molecular weight: 228.2

Ref: 54-BUP13473

Zebularine

CAS: 3690-10-6

Zebularine

Formula: C₉H₁₂N₂O₅

Purity: 98%

Color and Shape: Pale yellow Solid

Molecular weight: 228.20198

Ref: 54-BIA8416

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

CAS: 3690-10-6

Formula: C₉H₁₂N₂O₅

Purity: 98%

Color and Shape: Solid

Molecular weight: 228.2020

Ref: IN-DA00C0X2

Zebularine

CAS: 3690-10-6

Zebularine (4-Deoxyuridine) is a DNA methylation inhibitor.

Formula: C₉H₁₂N₂O₅

Purity: 99.04% - >99.99%

Color and Shape: Solid

Molecular weight: 228.2

Ref: TM-T2169

Zebularine

CAS: 3690-10-6

Formula: C₉H₁₂N₂O₅

Molecular weight: 228.21

Ref: 4Z-Z-019001

4-Deoxyuridine

CAS: 3690-10-6

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.

Formula: C₉H₁₂N₂O₅

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 228.21 g/mol

Ref: 3D-ND09503

Zebularine

CAS: 3690-10-6

Formula: C₉H₁₂N₂O₅

Molecular weight: 228.2

Ref: BE-RMCZ016000

ZEBULARINE

CAS: 3690-10-6

Formula: C₉H₁₂N₂O₅

Purity: 95%

Color and Shape: Solid

Molecular weight: 228.204

Ref: 10-F512872

Zebularine

CAS: 3690-10-6

1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

Formula: C₉H₁₂N₂O₅

Purity: 98%

Molecular weight: 228.2

Ref: IN-DG156999

Zebularine

Controlled Product

CAS: 3690-10-6

Applications It is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.
References Driscoll, J., et al.: J. Med. Chem., 34, 3280 (1991), Ueki, T., et al.: Cancer Res., 60, 1835 (2000),Sherr, C., et al.: Cell, 116, 235 (2004), Dote, H., et al.: Clin. Cancer Res.,11, 4571 ( 2005),

Formula: C₉H₁₂N₂O₅

Color and Shape: Neat

Molecular weight: 228.2

Ref: TR-Z276000

Zebularine

CAS: 3690-10-6

Formula: C₉H₁₂N₂O₅

Molecular weight: 228.2

Ref: ST-EA-CP-C151015