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

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

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 
• 951-78-0 2'-deoxyuridine 
• 50-89-5 thymidine 
• 890-38-0 2-deoxyinosine 
• 961-07-9 2'-Deoxyguanosine 
• 268217-18-1 2-fluoro-2'-O-[(cyanoethylthio)thiocarbonyl]-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 
• 111556-91-3 2-fluoro-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenosine 

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.

Thermodynamic Reaction Control of Nucleoside Phosphorolysis

Nucleoside analogs represent a class of important drugs for cancer and antiviral treatments. Nucleoside phosphorylases (NPases) catalyze the phosphorolysis of nucleosides and are widely employed for the synthesis of pentose-1-phosphates and nucleoside analogs, which are difficult to access via conventional synthetic methods. However, for the vast majority of nucleosides, it has been observed that either no or incomplete conversion of the starting materials is achieved in NPase-catalyzed reactions. For some substrates, it has been shown that these reactions are reversible equilibrium reactions that adhere to the law of mass action. In this contribution, we broadly demonstrate that nucleoside phosphorolysis is a thermodynamically controlled endothermic reaction that proceeds to a reaction equilibrium dictated by the substrate-specific equilibrium constant of phosphorolysis, irrespective of the type or amount of NPase used, as shown by several examples. Furthermore, we explored the temperature-dependency of nucleoside phosphorolysis equilibrium states and provide the apparent transformed reaction enthalpy and apparent transformed reaction entropy for 24 nucleosides, confirming that these conversions are thermodynamically controlled endothermic reactions. This data allows calculation of the Gibbs free energy and, consequently, the equilibrium constant of phosphorolysis at any given reaction temperature. Overall, our investigations revealed that pyrimidine nucleosides are generally more susceptible to phosphorolysis than purine nucleosides. The data disclosed in this work allow the accurate prediction of phosphorolysis or transglycosylation yields for a range of pyrimidine and purine nucleosides and thus serve to empower further research in the field of nucleoside biocatalysis. (Figure presented.).

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.

Synthesis of 2,6-dihalogenated purine nucleosides by thermostable nucleoside phosphorylases

The enzymatic transglycosylation of 2,6-dichloropurine (26DCP) and 6-chloro-2-fluoropurine (6C2FP) with uridine, thymidine and 1-(β-D-arabinofuranosyl)-uracil as the pentofuranose donors and recombinant thermostable nucleoside phosphorylases from G. thermoglucosidasius or T. thermophilus as biocatalysts was studied. Selection of 26DCP and 6C2FP as substrates is determined by their higher solubility in aqueous buffer solutions compared to most natural and modified purines and, furthermore, synthesized nucleosides are valuable precursors for the preparation of a large number of biologically important nucleosides. The substrate activity of 26DCP and 6C2FP in the synthesis of their ribo- and 2′-deoxyribo-nucleosides was closely similar to that of related 2-amino- (DAP), 2-chloro- and 2-fluoroadenines; the efficiency of the synthesis of β-D-arabinofuranosides of 26DCP and 6C2FP was lower vs. that of DAP under similar reaction conditions. For a convenient and easier recovery of the biocatalysts, the thermostable enzymes were immobilized on MagReSyn epoxide beads and the biocatalyst showed high catalytic efficiency in a number of reactions. As an example, 6-chloro-2-fluoro-(β-D-ribofuranosyl)-purine (9), a precursor of various antiviral and antitumour drugs, was synthesized by the immobilized enzymes at 60°C under high substrate concentrations (uridine:purine ratio of 2:1, mol). The synthesis was successfully scaled-up [uridine (2.5 mmol), base (1.25 mmol); reaction mixture 50 mL] to afford 9 in 60% yield. The reaction reveals the great practical potential of this enzymatic method for the efficient production of modified purine nucleosides of pharmaceutical interest.

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.

Convenient synthesis of 2′-deoxy-2-fluoroadenosine from 2-fluoroadenine

A convenient synthesis of 2′-deoxy-2-fluoroadenosine from commercially available 2-fluoroadenine is described. The coupling reaction of silylated 2-fluoroadenine with phenyl 3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-1-thio- D-erythro-pentofuranoside gave

Specific lipid conjugates to nucleoside diphosphates and their use as drugs

The present invention concerns new phospholipid derivatives of nucleosides of the general formula (I) in which R1represents a straight-chained or branched, saturated or unsaturated aliphatic residue with 9-14 carbon atoms which can optionally be substituted once or several times; R2can represent a straight-chained or branched, saturated or unsaturated aliphatic residue with 8-12 carbon atoms which can optionally be substituted once or several times; m is 2 or 3; A can represent a methylene group or an oxygen; Nuc can be a nucleoside or a residue derived from a nucleoside derivative; and tautomers thereof and their physiologically tolerated salts of inorganic and organic acids and bases as well as pharmaceutical preparations containing these compounds.

Process for the synthesis of oligonucleotides incorporating 2-aminoadenosine

This invention presents novel processes for incorporating 2-aminoadenosine and 2-aminoadenosine analogs into oligonucleotides. A halogenated adeninosine is incorporated into an oligonucleotide using standard synthesis methods, such as phosphoramidited pro

Lipid esters of nucleoside monophosphates and their use as immunosuppressive drugs

The present invention is directed to new nucleoside monophosphate derivatives of lipid ester residues of general formula (I) wherein R1 represents an optionally substituted alkyl chain having 1-20 carbon atoms; R2 represents hydrogen, an optionally substituted alkyl chain having 1-20 carbon atoms; R3, R4 and R5 represent hydrogen, hydroxy, azido, amino, cyano, or halogen; X represents a valence dash, oxygen, sulfur, a sulfinyl or sulfonyl group; Y represents a valence dash, an oxygen or sulfur atom; B represents a purine and/or pyrimidine base; with the proviso that at least one of the residues R3 or R5 is hydrogen; to their tautomers and their physiologically acceptable salts of inorganic and organic acids and/or bases, as well as to processes for their preparation, and to drugs containing said compounds.