21679-12-9

Basic information

• Product Name: 2'-DEOXY-2-FLUOROADENOSINE
• Synonyms: 2'-DEOXY-2-FLUOROADENOSINE;2-Fluoro-2'-deoxyadenosine 96%;NSC 114093;2-Fluorodeoxyadenosine
• CAS NO: 21679-12-9
• Molecular Formula: C₁₀H₁₂FN₅O₃
• Molecular Weight: 269.23
• EINECS: 1312995-182-4
• Product Categories: Nucleosides;Oligonucleotide Synthesis;Specialty Synthesis
• Mol File: 21679-12-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 218 °C (dec.)
• Boiling Point: 696.7 °C at 760 mmHg
• Flash Point: 375.1 °C
• Appearance: white to of-white crystals
• Density: 2.01 g/cm³
• CAS DataBase Reference: 2'-DEOXY-2-FLUOROADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-DEOXY-2-FLUOROADENOSINE(21679-12-9)
• EPA Substance Registry System: 2'-DEOXY-2-FLUOROADENOSINE(21679-12-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 21679-12-9(Hazardous Substances Data)

Usage

Description

2'-Deoxy-2-fluoroadenosine is a synthetic nucleoside analog that exhibits unique biological properties and potential therapeutic applications. It is structurally similar to adenosine, a naturally occurring nucleoside in cells, but with a fluorine atom replacing the hydroxyl group at the 2' position. This modification endows 2'-deoxy-2-fluoroadenosine with distinct chemical and biological characteristics, making it a promising candidate for various applications in the fields of medicine and biotechnology.

Uses

Used in Antimicrobial Applications:
2'-Deoxy-2-fluoroadenosine is used as an antimicrobial agent for combating metronidazole-resistant Trichomonas vaginalis, a parasitic infection that causes trichomoniasis. Its unique structure allows it to bypass the resistance mechanisms associated with metronidazole, making it a potential alternative treatment for drug-resistant infections.
Used in Anticancer Applications:
2'-Deoxy-2-fluoroadenosine is used as a potent anticancer agent, exhibiting both killing effects on tumor cells and bystander effects that target neighboring cancer cells. It forms a suicide system with purine nucleosides, leading to the production of toxic metabolites that cause cell death. This mechanism of action makes it a promising candidate for cancer therapy, particularly for tumors that have developed resistance to conventional treatments.
Used in Drug Development:
2'-Deoxy-2-fluoroadenosine is used as a starting point for the development of new drugs and therapeutic agents. Its unique chemical properties and biological activities make it an attractive scaffold for the design and synthesis of novel compounds with improved pharmacological profiles. Researchers can modify its structure to enhance its potency, selectivity, and pharmacokinetic properties, potentially leading to the discovery of more effective treatments for various diseases.
Used in Biomedical Research:
2'-Deoxy-2-fluoroadenosine is used as a research tool in the study of cellular processes and mechanisms. Its unique interactions with cellular components and enzymes can provide valuable insights into the molecular basis of various diseases and help identify new targets for therapeutic intervention. Additionally, it can be used to probe the mechanisms of drug resistance and develop strategies to overcome this challenge in clinical settings.

Upstream product

• 259528-01-3 2'-deoxy-2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 
• 675598-20-6 2-fluoro-9-(3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-D-erythro-pentofuranosyl)adenine 
• 452-51-7 D-2-deoxyribose 
• 700-49-2 2-fluoroadenine 
• 675598-22-8 tert-butyl (((2R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-methoxytetrahydrofuran-2-yl)methoxy)dimethylsilane 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 174289-74-8 phenyl 3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-1-thio-D-erythro-pentofuranoside 
• 146-78-1 2-fluoroadenosine 
• 111556-91-3 2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 
• 268217-17-0 2-fluoro-2'-O-[(1-imidazolyl)thiocarbonyl]-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 
• 268217-18-1 2-fluoro-2'-O-[(cyanoethylthio)thiocarbonyl]-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 
• 951-78-0 2'-deoxyuridine 
• 50-89-5 thymidine 
• 890-38-0 2-deoxyinosine 

Downstream Products

• 17039-17-7 2-deoxy–α-D-ribose 1-phosphate 
• 700-49-2 2-fluoroadenine 
• 1182278-84-7 8-phenyl-2-(N-piperidyl)-2'-deoxyadenosine 

Relevant articles and documents

A convenient synthesis of 2'-deoxy-2-fluoroadenosine; a potential prodrug for suicide gene therapy

A convenient synthesis of 2'-deoxy-2-fluoro-adenosine (1) is described. Deaminative fluorination of 2-aminoadenosine (2) followed by silylation of the 3', 5'-hydroxyl groups gave the corresponding 2-fluoroadenosine derivative 4 in good yield. Thiocarbonylation of 4 to thiocarbonylimidazolyl derivative 5a followed by treatment with an excess of tris(trimethylsilyl)silane (TTMSS) and tert-butyl peroxide in toluene at 80 °C was found to affect an efficient deoxygenation to the corresponding 2'- deoxy derivative 6. Desilylation of 6 by Et4NF in CH3CN afforded 1 in high yield.

Enzymatic Synthesis of Therapeutic Nucleosides using a Highly Versatile Purine Nucleoside 2’-DeoxyribosylTransferase from Trypanosoma brucei

The use of enzymes for the synthesis of nucleoside analogues offers several advantages over multistep chemical methods, including chemo-, regio- and stereoselectivity as well as milder reaction conditions. Herein, the production, characterization and utilization of a purine nucleoside 2’-deoxyribosyltransferase (PDT) from Trypanosoma brucei are reported. TbPDT is a dimer which displays not only excellent activity and stability over a broad range of temperatures (50–70 °C), pH (4–7) and ionic strength (0–500 mM NaCl) but also an unusual high stability under alkaline conditions (pH 8–10). TbPDT is shown to be proficient in the biosynthesis of numerous therapeutic nucleosides, including didanosine, vidarabine, cladribine, fludarabine and nelarabine. The structure-guided replacement of Val11 with either Ala or Ser resulted in variants with 2.8-fold greater activity. TbPDT was also covalently immobilized on glutaraldehyde-activated magnetic microspheres. MTbPDT3 was selected as the best derivative (4200 IU/g, activity recovery of 22 %), and could be easily recaptured and recycled for >25 reactions with negligible loss of activity. Finally, MTbPDT3 was successfully employed in the expedient synthesis of several nucleoside analogues. Taken together, our results support the notion that TbPDT has good potential as an industrial biocatalyst for the synthesis of a wide range of therapeutic nucleosides through an efficient and environmentally friendly methodology.

Aeromonas hydrophila strains as biocatalysts for transglycosylation

Microbial transglycosylation is useful as a green alternative in the preparation of purine nucleosides and analogues, especially for those that display pharmacological activities. In a search for new transglycosylation biocatalysts, two Aeromonas hydrophila strains were selected. The substrate specificity of both micro-organisms was studied and, as a result, several nucleoside analogues have been prepared. Among them, ribavirin, a broad spectrum antiviral, and the well-known anti HIV didanosine, were prepared, in 77 and 62% yield using A. hydrophila CECT 4226 and A. hydrophila CECT 4221, respectively. In order to scale-up the processes, the reaction conditions, product purification and biocatalyst preparation were analyzed and optimized.