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3'-Azido-3'-deoxy-beta-L-uridine

Cat No.:V31754 Purity: ≥98%
3'-Azido-3'-deoxy-beta-L-uridine (Compound 25) is a nucleoside analogue.
3'-Azido-3'-deoxy-beta-L-uridine
3'-Azido-3'-deoxy-beta-L-uridine Chemical Structure CAS No.: 2095417-28-8
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
3'-Azido-3'-deoxy-beta-L-uridine (Compound 25) is a nucleoside analogue. 3'-Azido-3'-deoxy-beta-L-uridine is a reagent for click chemistry. It has an Azide (N3) moiety and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing an Alkyne group. SPAAC (Strain-promoted alkyne-azide cycloaddition) may also happen with compounds bearing a BCN or DBCO group.
3'-Azido-3'-deoxy-beta-L-uridine (Compound 25) is a nucleoside derivative. With a molecular formula of C₉H11N₅O₅ and a molecular weight of 269.21 g/mol, it is a nucleoside analogue that serves as a reagent for click chemistry. It has an Azide (N3) moiety and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with compounds bearing an alkyne group. The compound is used as a building block for the synthesis of labeled or functionalized nucleosides and nucleotides for various research applications.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary targets of 3'-Azido-3'-deoxy-beta-L-uridine are not well-defined as specific receptors or enzymes, as it is primarily used as a chemical reagent rather than a therapeutic agent. The compound is a nucleoside derivative that can be incorporated into nucleic acids or used as a building block for the synthesis of modified oligonucleotides. Its azide moiety allows for bioorthogonal conjugation reactions, enabling the labeling and functionalization of biomolecules. The compound may also have potential as an antiviral agent, as nucleoside analogs are often used to inhibit viral replication by interfering with nucleic acid synthesis, but its specific antiviral activity has not been characterized.
ln Vitro
In vitro studies of 3'-Azido-3'-deoxy-beta-L-uridine are focused on its use as a click chemistry reagent and building block for nucleoside analog synthesis. The compound's azide moiety allows for copper-catalyzed azide-alkyne cycloaddition (CuAAc) with alkyne-bearing compounds. This makes it useful for labeling nucleosides, nucleotides, and oligonucleotides with fluorescent tags, biotin, or other functional groups. The compound can be incorporated into DNA or RNA strands during synthesis, enabling the study of nucleic acid structure, function, and interactions. Its utility in click chemistry makes it a valuable tool for chemical biology and molecular biology research.
ln Vivo
In vivo studies of 3'-Azido-3'-deoxy-beta-L-uridine are not typically performed, as it is primarily used as a chemical reagent for in vitro applications rather than a therapeutic agent. As a nucleoside derivative, it could potentially be incorporated into nucleic acids in vivo, but its stability, bioavailability, and metabolic fate would need to be characterized. The compound's azide moiety could be used for bioorthogonal labeling in vivo if suitable alkyne-bearing probes are available. Further studies would be needed to evaluate its potential for in vivo applications.
Enzyme Assay
For in vitro enzyme/receptor binding assays, 3'-Azido-3'-deoxy-beta-L-uridine is not typically used as a direct enzyme inhibitor or receptor ligand. However, it can be used as a substrate for nucleoside kinases or other enzymes that phosphorylate nucleosides. The compound's conversion to its mono-, di-, or triphosphate form can be monitored using HPLC or mass spectrometry. Its incorporation into nucleic acids by polymerases can be studied using in vitro transcription or replication assays. The compound's azide moiety allows for subsequent detection or conjugation via click chemistry. Standard assay conditions include appropriate buffer systems and cofactors.
Cell Assay
For in vitro cellular experiments, 3'-Azido-3'-deoxy-beta-L-uridine can be added to cell culture media to study its cellular uptake and metabolism. Cells are cultured in appropriate media and treated with various concentrations of the compound. Cellular uptake can be assessed using labeled or fluorescent derivatives. The compound's incorporation into cellular nucleic acids can be detected using click chemistry with alkyne-bearing fluorescent probes. Effects on cell viability and proliferation are monitored. The compound's potential as an antiviral agent can be assessed in virus-infected cells by measuring viral replication.
Animal Protocol
For in vivo animal experiments, 3'-Azido-3'-deoxy-beta-L-uridine is not typically administered to animals for therapeutic purposes. However, it could be used in preclinical studies to evaluate its pharmacokinetic properties and potential toxicity if it were being developed as an antiviral agent. The compound could be administered via various routes, and its distribution, metabolism, and excretion could be studied. Its incorporation into nucleic acids in vivo could be detected using click chemistry. Animal studies would follow appropriate ethical guidelines.
ADME/Pharmacokinetics
Pharmacokinetic properties of 3'-Azido-3'-deoxy-beta-L-uridine are not characterized, as it is primarily used as a chemical reagent rather than a therapeutic agent. As a nucleoside with a molecular weight of 269.21 g/mol, it may have limited oral bioavailability and rapid clearance. When administered systemically, the compound would likely be metabolized by nucleoside kinases and other enzymes. Its half-life in circulation would depend on its stability and clearance mechanisms. Further pharmacokinetic studies would be needed to fully characterize its absorption, distribution, metabolism, and excretion profile in vivo.
Toxicity/Toxicokinetics
Toxicological data for 3'-Azido-3'-deoxy-beta-L-uridine are limited, as it is primarily used as a chemical reagent. As a nucleoside analog, its toxicity would depend on its incorporation into nucleic acids and its effects on cellular metabolism. Azide-containing compounds can be toxic at high concentrations, and appropriate safety precautions should be taken. Standard toxicological assessments would include cytotoxicity screening in relevant cell lines. As with all research chemicals, appropriate safety precautions should be taken when handling 3'-Azido-3'-deoxy-beta-L-uridine, including the use of personal protective equipment and adherence to institutional safety guidelines.
References

[1]. Synthesis of 3'-Azido-D/L-nucleosides. Chinese Journal of Organic Chemistry, 2018, 38(1): 138-147.

Additional Infomation
3'-Azido-3'-deoxy-beta-L-uridine is a research compound used as a click chemistry reagent and building block for nucleoside analog synthesis. No clinical trials or regulatory approvals have been reported for this compound as a therapeutic agent. It is available from various chemical suppliers for research purposes only. The compound is a nucleoside derivative with an Azide (N3) moiety that can undergo CuAAc with alkyne-bearing compounds. It is a valuable tool for labeling and functionalizing nucleosides, nucleotides, and nucleic acids.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H11N5O5
Molecular Weight
269.214141130447
Exact Mass
269.076
CAS #
2095417-28-8
PubChem CID
137628663
Appearance
White to off-white solid powder
LogP
-1.3
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
3
Heavy Atom Count
19
Complexity
474
Defined Atom Stereocenter Count
4
SMILES
O1[C@@H](CO)[C@@H]([C@@H]([C@H]1N1C=CC(NC1=O)=O)O)N=[N+]=[N-]
InChi Key
WQBCHXWMHQMQKW-PSQAKQOGSA-N
InChi Code
InChI=1S/C9H11N5O5/c10-13-12-6-4(3-15)19-8(7(6)17)14-2-1-5(16)11-9(14)18/h1-2,4,6-8,15,17H,3H2,(H,11,16,18)/t4-,6-,7-,8-/m0/s1
Chemical Name
1-[(2S,3S,4R,5R)-4-azido-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~464.32 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.73 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (7.73 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (7.73 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.7146 mL 18.5729 mL 37.1457 mL
5 mM 0.7429 mL 3.7146 mL 7.4291 mL
10 mM 0.3715 mL 1.8573 mL 3.7146 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.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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