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Zebularine

Catalog Number: BT-253004

CAS Number: 3690-10-6

Molecular Formula: C₉H₁₂N₂O₅

Molecular Weight: 228.2 g/mol

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Product Introduction

Description

Zebularine is a pyrimidine nucleoside analog that has gained significant attention in recent years due to its potential therapeutic applications in various diseases, including cancer, viral infections, and inflammation. It is a cytidine analog that inhibits DNA methylation and has shown promising results in preclinical studies. This paper aims to provide a comprehensive review of zebularine, including its method of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges.

Properties

CAS Number

3690-10-6

Product Name

Zebularine

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

Molecular Formula

C₉H₁₂N₂O₅

Molecular Weight

228.2 g/mol

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

RPQZTTQVRYEKCR-WCTZXXKLSA-N

SMILES

C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O

Synonyms

4-deoxyuridine
NSC 309132
pyrimidin-2-one beta-D-ribofuranoside
pyrimidin-2-one beta-ribofuranoside
pyrimidin-2-one beta-ribofuranoside, (L)-isomer
pyrimidin-2-one ribonucleoside
zebularine

Canonical SMILES

C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O

Isomeric SMILES

C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O

Method of Synthesis or Extraction

Zebularine can be synthesized using various methods, including chemical synthesis, enzymatic synthesis, and microbial fermentation. Chemical synthesis involves the reaction of cytosine with ribose or deoxyribose, followed by the addition of a methyl group to the nitrogen atom at position 5. Enzymatic synthesis involves the use of cytidine deaminase to convert cytidine to uridine, followed by the addition of a methyl group to the nitrogen atom at position 5. Microbial fermentation involves the use of microorganisms, such as Streptomyces sp. or Pseudomonas sp., to produce zebularine. The efficiency and yield of each method vary, with chemical synthesis being the most efficient and microbial fermentation being the least efficient. Environmental and safety considerations should be taken into account when selecting a method, as chemical synthesis can produce hazardous waste, while microbial fermentation can have a significant environmental impact.

Chemical Structure and Biological Activity

Zebularine has a pyrimidine ring attached to a ribose sugar and a nitrogenous base. It is structurally similar to cytidine, with the addition of a nitrogen atom at position 5. Zebularine inhibits DNA methylation by forming a covalent bond with DNA methyltransferases, leading to the degradation of the enzyme and the inhibition of DNA methylation. It has shown potent antitumor activity in various cancer cell lines, including breast, lung, and colon cancer. It also has antiviral and anti-inflammatory properties, making it a potential therapeutic agent for viral infections and inflammatory diseases.

Biological Effects

Zebularine has been shown to affect cell function and signal transduction by inhibiting DNA methylation and altering gene expression. It has also been shown to induce apoptosis and cell cycle arrest in cancer cells, leading to tumor growth inhibition. However, zebularine can have potential toxic effects, including hepatotoxicity and nephrotoxicity, which should be taken into consideration when developing therapeutic applications.

Applications

Zebularine has potential applications in medical research, including its role in drug development, clinical trials, and findings. It has shown promising results in preclinical studies as a potential therapeutic agent for various diseases, including cancer, viral infections, and inflammation. In environmental research, zebularine can have effects on ecosystems and can play a role in pollution management and sustainability. In industrial research, zebularine can be used in manufacturing processes to improve product quality and efficiency, with health and safety considerations taken into account.

Future Perspectives and Challenges

Current limitations in the use and study of zebularine include its low bioavailability and potential toxic effects. Possible solutions and improvements include the development of prodrugs and nanocarriers to improve bioavailability and reduce toxicity. Future trends and prospects in the application of zebularine in scientific research include its potential use in combination therapy and personalized medicine.
Conclusion:
Zebularine is a promising nucleoside analog with potential therapeutic applications in various diseases. Its method of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges have been discussed in this paper. Further research is needed to fully understand the potential of zebularine and to develop safe and effective therapeutic applications.

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