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| Targets |
As a nucleoside analog, 3'-Deoxy-3'-fluoroadenosine targets DNA and RNA polymerases. It is taken up by cells and phosphorylated to its active triphosphate form. The 3'-fluoro modification is likely to act as a non-obligate chain terminator, as the absence of a 3'-OH prevents the addition of subsequent nucleotides during nucleic acid synthesis, leading to the inhibition of viral genome replication or cancer cell proliferation.
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| ln Vitro |
In vitro, 3'-Deoxy-3'-fluoroadenosine exhibits a wide range of anti-tumor activity, targeting indolent lymphoid malignancies. Its anticancer mechanism relies on inhibiting DNA synthesis and inducing apoptosis. It also shows potent antiviral activity, inhibiting viruses such as Tick-borne encephalitis virus (TBEV), Zika virus, and West Nile virus (WNV) with EC50 values of 1.1 uM.
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| ln Vivo |
Specific in vivo efficacy data for this compound is not detailed in the provided literature. However, as a purine nucleoside analog, it is expected to have antitumor and antiviral activity in animal models. Its structure is designed for potential in vivo use, and it would likely be evaluated in xenograft mouse models for cancer or in infection models for antiviral activity.
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| Enzyme Assay |
For a cell-free system, the mechanism can be assessed using a RNA-dependent RNA polymerase (RdRp) inhibition assay. The purified viral polymerase, an RNA template, and a mixture of nucleotides, including the 3'-Deoxy-3'-fluoroadenosine triphosphate (the active metabolite), are incubated. The effect of the compound on RNA synthesis is measured by gel electrophoresis or by quantifying the incorporation of radiolabeled nucleotides.
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| Cell Assay |
In cellular assays, cancer or virus-infected cell lines are seeded in 96-well plates and treated with serial dilutions of 3'-Deoxy-3'-fluoroadenosine (e.g., 0.1 uM to 100 uM) for 48-72 hours. Cell viability is measured using an MTT or CellTiter-Glo assay to determine an IC50. For antiviral studies, a reduction in viral titer or a cytopathic effect (CPE) reduction assay is used to calculate the EC50.
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| Animal Protocol |
For in vivo studies, 3'-Deoxy-3'-fluoroadenosine would typically be formulated in a vehicle such as PBS or a DMSO-based solution (e.g., DMSO: PEG300: Tween-80: Saline). It can be administered to mice via intravenous (IV), intraperitoneal (IP), or oral gavage (p.o.) depending on its pharmacokinetic properties. In a xenograft model, tumor volume is measured to assess anti-tumor activity.
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| ADME/Pharmacokinetics |
Specific ADME data is not provided. However, as a nucleoside analog, it is expected to be soluble in water, facilitating its use in in vitro assays. Its oral bioavailability may be limited due to its polar nature, so it is often administered via injection for systemic effects. The compound is likely metabolized by deaminases and phosphorylated by cellular kinases to its active triphosphate form in vivo.
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| Toxicity/Toxicokinetics |
No specific toxicology data for 3'-Deoxy-3'-fluoroadenosine is presented. As a nucleoside analog, its toxicity profile is generally attributed to off-target effects on rapidly dividing host cells, particularly in the bone marrow and gastrointestinal tract. However, detailed safety data is a key part of preclinical development, which is not available for this specific research chemical.
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| References | |
| Additional Infomation |
The structure given in the first document
3'-Deoxy-3'-fluoroadenosine is a potent example of a 3'-modified nucleoside analog, which has been a rich source of antiviral and anticancer drugs. The substitution of the 3'-OH with a fluorine atom can enhance metabolic stability and alter the binding affinity to the target polymerase. The compound's activity against flaviviruses like Zika and West Nile is particularly noteworthy for emerging infectious disease research. It is a preclinical research tool. |
| Molecular Formula |
C10H12FN5O3
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|---|---|
| Molecular Weight |
269.23
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| Exact Mass |
269.092
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| CAS # |
75059-22-2
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| PubChem CID |
122619
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| Appearance |
White to off-white solid powder
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| Boiling Point |
628.6°C at 760 mmHg
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| Flash Point |
334°C
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| LogP |
-0.6
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
19
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| Complexity |
338
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)F)O)N
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| InChi Key |
QCDAWXDDXYQEJJ-QYYRPYCUSA-N
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| InChi Code |
InChI=1S/C10H12FN5O3/c11-5-4(1-17)19-10(7(5)18)16-3-15-6-8(12)13-2-14-9(6)16/h2-5,7,10,17-18H,1H2,(H2,12,13,14)/t4-,5-,7-,10-/m1/s1
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| Chemical Name |
(2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-4-fluoro-5-(hydroxymethyl)oxolan-3-ol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.7143 mL | 18.5715 mL | 37.1430 mL | |
| 5 mM | 0.7429 mL | 3.7143 mL | 7.4286 mL | |
| 10 mM | 0.3714 mL | 1.8571 mL | 3.7143 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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