2'-Fluoro-2'-deoxyuridine
[CAS# 784-71-4]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 2'-Fluoro-2'-deoxyuridine
• Synonyms: 2'-Deoxy-2'-fluorouridine; 2-FdU
• Molecular Formula: C₉H₁₁FN₂O₅
• Molecular Weight: 246.19
• Protein Sequence: N
• CAS Registry Number: 784-71-4
• EC Number: 810-296-0
• SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)F

Properties

• Index of Refraction: 53

Safety Data

• Hazard Symbols: GHS02 Danger
• Risk Statements: H228
• Safety Statements: P210-P240-P241-P280-P370+P378

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable solids	Flam. Sol.	2	H228

Discovery and Applications

2'-Fluoro-2'-deoxyuridine is a well-known nucleoside analog that has attracted much attention in the field of medicinal chemistry. This compound features a fluorine atom substituted at the 2' position of the sugar moiety and has proven to be a valuable tool in antiviral and anticancer therapy due to its enhanced stability and unique biochemical properties.

The discovery of 2'-fluoro-2'-deoxyuridine is part of an ongoing effort to develop nucleoside analogs with improved therapeutic properties. Researchers aim to create modified nucleosides that resist enzymatic degradation and exhibit increased efficacy against target diseases. The introduction of a fluorine atom at the 2' position of deoxyuridine produces compounds with excellent stability and unique biological activity. This modification was first reported in the mid-20th century and marked a major advance in the design of nucleoside analogs.

2'-Fluoro-2'-deoxyuridine has shown potential as an antiviral agent. Its ability to be incorporated into viral DNA during replication can lead to chain termination or mutagenesis, effectively inhibiting viral proliferation. This mechanism makes it a promising candidate for the treatment of various viral infections, including herpes simplex virus and hepatitis B. Its enhanced stability can more effectively inhibit viral activity than unmodified nucleosides.

In the field of oncology, 2'-fluoro-2'-deoxyuridine is explored for its potential as a chemotherapeutic agent. Cancer cells exhibit rapid division and high metabolic activity, making them particularly vulnerable to nucleoside analogs that disrupt DNA synthesis. The compound can be incorporated into the DNA of cancer cells, interfering with replication and inducing cell death. This property makes it a candidate for the treatment of certain types of cancer, including gastrointestinal and colorectal cancers.

The stability and unique properties of 2'-fluoro-2'-deoxyuridine 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 use 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'-deoxyuridine 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 can help design nucleoside drugs with improved bioavailability and therapeutic properties, ultimately providing more effective treatments for a variety of diseases.

References

2022. Isolation and Characterization of Engineered Nucleoside Deoxyribosyltransferase with Enhanced Activity Toward 2'-Fluoro-2'-Deoxynucleoside. Journal of Microbiology and Biotechnology, 32(7).
DOI: 10.4014/jmb.2204.04041

2005. Synthesis and anti-viral activity of a series of d- and l-2′-deoxy-2′-fluororibonucleosides in the subgenomic HCV replicon system. Bioorganic & Medicinal Chemistry, 13(5).
DOI: 10.1016/j.bmc.2004.12.011

1996. Simple and effective method for the synthesis of 3′,5′-substituted 1-β-D-arabinofuranosyluracil. Chemistry of Heterocyclic Compounds, 32(7).
DOI: 10.1007/bf01165730