2'-Fluoro-2'-deoxyadenosine
[CAS# 64183-27-3]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 2'-Fluoro-2'-deoxyadenosine
• Synonyms: (2R,3R,4R,5R)-5-(6-Aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
• Molecular Formula: C₁₀H₁₂FN₅O₃
• Molecular Weight: 269.23
• Protein Sequence: N
• CAS Registry Number: 64183-27-3
• EC Number: 814-045-6
• SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)F)N

Properties

• Melting point: 228-231 °C
• Boiling point: point

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2'-Fluoro-2'-deoxyadenosine* is a notable nucleoside analog in the field of medicinal chemistry and biochemistry. The compound features a fluorine atom replacing the 2'-hydroxyl group and is of great interest for antiviral and anticancer therapies due to its enhanced stability and unique biochemical properties.

The discovery of 2'-Fluoro-2'-deoxyadenosine stems from the need to develop more effective therapeutic agents that are resistant to enzymatic degradation. Researchers have sought to modify naturally occurring nucleosides to improve their stability and efficacy. The introduction of a fluorine atom at the 2' position of deoxyadenosine renders the compound more resistant to enzymatic degradation and alters its biological activity. This modification was first reported in the late 20th century and marked a major advance in the design of nucleoside analogs.

2'-Fluoro-2'-deoxyadenosine has been extensively studied for its antiviral properties. The compound can be incorporated into viral DNA during replication, resulting in chain termination or lethal mutagenesis, thereby effectively inhibiting viral replication. This mechanism makes it a promising candidate for the treatment of various viral infections, including HIV and hepatitis B. The enhanced stability of this analogue compared to the unmodified analogue allows for more effective inhibition of viral activity.

In oncology, 2'-fluoro-2'-deoxyadenosine shows promise as a chemotherapeutic agent. Cancer cells, characterized by rapid division and high metabolic activity, are particularly susceptible to nucleoside analogs that interfere with DNA synthesis. This compound can be incorporated into the DNA of cancer cells, disrupting replication and inducing cell death. Its unique properties make it a candidate for the treatment of certain types of cancer, including leukemias and lymphomas.

The stability and unique properties of 2'-fluoro-2'-deoxyadenosine make it a valuable tool in biochemical research. It is used to study DNA synthesis and repair mechanisms, providing insights into fundamental processes in cell biology. Researchers have used this compound to study the effects of nucleoside modifications on DNA structure and function, thereby deepening our understanding of gene regulation and expression.

Because 2'-fluoro-2'-deoxyadenosine is resistant to enzymatic degradation, it can be used in pharmacokinetic studies to evaluate the absorption, distribution, metabolism, and excretion (ADME) of nucleoside analogs. These studies will help design nucleoside drugs with improved bioavailability and therapeutic properties, ultimately providing more effective treatments for various diseases.

References

1981. Synthesis and characterization of the dinucleoside monophosphates containing 2'-fluoro-2'-deoxyadenosine. Biochemistry, 20(10).
DOI: 10.1021/bi00514a011

2024. Sugar-modified nucleosides from simple ingredients. Nature Synthesis, 3(11).
DOI: 10.1038/s44160-024-00645-y

2019. Sustainable production of nucleoside analogues by a high-efficient purine 2'-deoxyribosyltransferase immobilized onto Ni2+ chelate magnetic microparticles. Bioresource Technology, 291.
DOI: 10.1016/j.biortech.2019.121772