2'-O-(2-Methoxyethyl)adenosine
[CAS# 168427-74-5]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: 2'-O-(2-Methoxyethyl)adenosine
• Synonyms: (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-(2-methoxyethoxy)oxolan-3-ol
• Molecular Formula: C₁₃H₁₉N₅O₅
• Molecular Weight: 325.32
• Protein Sequence: N
• CAS Registry Number: 168427-74-5
• SMILES: COCCO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

2'-O-(2-methoxyethyl)adenosine, often abbreviated as 2'-O-(2-ME)Ado, is a modified nucleoside that represents a significant advance in stability and therapeutic potential. The compound represents an innovative step forward in nucleoside chemistry aimed at improving the efficacy of nucleoside drugs and research tools.

The synthesis of 2'-O-(2-ME)Ado stems from efforts to improve the stability and bioavailability of adenosine, a key nucleoside in cellular metabolism and signaling. By modifying the 2' position of the ribose sugar with a 2-methoxyethyl group, the researchers aimed to create a nucleoside that would resist degradation by nucleases, which often limit the effectiveness of adenosine compounds in therapeutic applications.

The chemical modification involves attaching a 2-methoxyethyl group to the 2'-hydroxyl group of adenosine, a change that prevents the compound from rapidly breaking down in biological systems. This enhancement extends the half-life of the nucleoside and increases its cellular uptake rate.

2'-O-(2-ME)Ado is being explored for use in antiviral and anticancer therapies. This modification enhances the compound's stability, making it a more effective inhibitor of nucleic acid synthesis in pathogens and cancer cells. Its increased resistance to enzymatic degradation allows it to be maintained at therapeutic levels in vivo, thus increasing its potential as a treatment for diseases involving rapid cell proliferation or viral replication.

In cell signaling studies, 2'-O-(2-ME)Ado is used to investigate the role of adenosine in regulating various physiological processes. The compound's enhanced stability makes it an ideal tool for studying adenosine receptor interactions and signaling pathways. This research helps to elucidate the mechanisms by which adenosine affects cellular function and its potential as a therapeutic target.

The unique properties of 2'-O-(2-ME)Ado provide valuable insights into drug design. The stability conferred by the 2-methoxyethyl group enables the development of novel adenosine-based drugs with improved pharmacokinetic profiles. These modifications could result in more effective drugs with fewer side effects, providing new treatment options for a range of diseases.

References

2004. Chemo-enzymatic synthesis of 2′-O-methoxyethyl ribonucleosides using a phosphodiesterase from Serratia marcescens. Applied Microbiology and Biotechnology.
DOI: https://pubmed.ncbi.nlm.nih.gov/15349700