2'-Deoxy-2'-fluoro-N-isobutyrylguanosine
[CAS# 80681-25-0]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 2'-Deoxy-2'-fluoro-N-isobutyrylguanosine
• Synonyms: 2'-Deoxy-2'-fluoro-N-(2-methyl-1-oxopropyl)guanosine
• Molecular Formula: C₁₄H₁₈FN₅O₅
• Molecular Weight: 355.32
• CAS Registry Number: 80681-25-0
• SMILES: CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)F

Properties

• Solubility: Very slightly soluble (0.31 g/L) (25 °C), Calc.^*
• Density: 1.78±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H320-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

2'-Deoxy-2'-fluoro-N-isobutyrylguanosine is a nucleoside analog that has attracted much attention for its unique chemical properties and potential therapeutic applications. The compound features a fluorine atom at the 2' position of the deoxyribose sugar and an isobutyryl group on the guanine base. These modifications enhance the stability and functionality of the nucleoside, making it a valuable tool in antiviral therapy, cancer treatment, and biochemical research.

The discovery of 2'-deoxy-2'-fluoro-N-isobutyrylguanosine is part of a broad effort to develop nucleoside analogs with improved therapeutic properties. Researchers aim to create compounds that resist enzymatic degradation and maintain or enhance biological activity. The introduction of a fluorine atom at the 2' position and an isobutyryl group on the guanine base are strategic modifications designed to increase the stability of the compound and alter its biochemical interactions. These modifications were first reported in the second half of the 20th century and marked a major advance in the design of nucleoside analogs.

2'-Deoxy-2'-fluoro-N-isobutyrylguanosine has shown potential as an antiviral agent. Its incorporation into viral DNA can lead to chain termination or induce mutations that inhibit viral replication. This mechanism makes it a candidate drug for the treatment of various viral infections, including those caused by herpes viruses and hepatitis B. The enhanced stability provided by fluorine and isobutyryl modifications can more effectively inhibit viral activity, making it a valuable addition to the development of antiviral drugs.

In oncology, 2'-deoxy-2'-fluoro-N-isobutyrylguanosine is explored for its potential as a chemotherapeutic agent. Cancer cells, characterized by rapid division and high metabolic activity, are particularly susceptible to nucleoside analogs that disrupt DNA synthesis. Incorporation of 2'-deoxy-2'-fluoro-N-isobutyrylguanosine into the DNA of cancer cells interferes with the replication process, leading to cell death. This property makes it a candidate drug for the treatment of certain types of cancer, such as hematological malignancies and solid tumors.

The stability and unique properties of 2'-deoxy-2'-fluoro-N-isobutyrylguanosine make it a valuable tool in biochemical research. It is used to study DNA synthesis and repair mechanisms, providing insights into fundamental cellular processes. 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'-deoxy-2'-fluoro-N-isobutyrylguanosine 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 are critical to designing nucleoside drugs with improved bioavailability and therapeutic properties, thereby providing more effective treatments for a variety of diseases.

References

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