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2′-O-(2-Methoxyethyl)adenosine

Alias: 2'-O-(2-Methoxyethyl)adenosine; 2'-O-(2-Methoxyethyl)-adenosine; Adenosine, 2'-O-(2-methoxyethyl)-; 2'-MOE-Adenosine
Cat No.:V52985 Purity: ≥98%
2′-O-(2-Methoxyethyl)adenosine is a compound useful in the preparation /synthesis of oligonucleotides.
2′-O-(2-Methoxyethyl)adenosine
2′-O-(2-Methoxyethyl)adenosine Chemical Structure CAS No.: 168427-74-5
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2′-O-(2-Methoxyethyl)adenosine is a compound useful in the preparation /synthesis of oligonucleotides.
2′-O-(2-Methoxyethyl)adenosine (CAS# 168427-74-5), also known as MOEA, is a modified nucleoside that has gained significant attention due to its potential therapeutic applications. It is a 2′-O-methoxyethyl derivative of the purine nucleoside adenosine. The compound has a molecular formula of C13H19N5O5 and a molecular weight of 325.32-325.33. 2′-O-(2-Methoxyethyl)adenosine is widely used as a synthetic intermediate and pharmacological tool in oligonucleotide chemistry, nucleoside therapeutics, and biochemical studies.
Biological Activity I Assay Protocols (From Reference)
Targets
2′-O-(2-Methoxyethyl)adenosine does not have a specific biological target itself but serves as a modified nucleoside building block for oligonucleotide therapeutics. When incorporated into oligonucleotides, the 2′-O-methoxyethyl (MOE) modification enhances nuclease resistance and increases binding affinity to complementary RNA targets. The resulting modified oligonucleotides can target various biological molecules including mRNA for antisense applications. The compound has been used in VEGF-binding aptamers.
ln Vitro
The in vitro activity of 2′-O-(2-Methoxyethyl)adenosine is assessed by its utility as a building block in oligonucleotide synthesis. The efficiency of incorporation into growing oligonucleotide chains during solid-phase synthesis is evaluated by monitoring coupling efficiency. The resulting MOE-modified oligonucleotides are evaluated for their binding affinity to complementary RNA targets using thermal melting (Tm) analysis. The compound is a nucleoside analog used to improve RNA target affinity and nuclease resistance of therapeutic oligonucleotides.
ln Vivo
In vivo studies for 2′-O-(2-Methoxyethyl)adenosine are typically conducted on the modified oligonucleotides incorporating this nucleoside rather than the monomer itself. These oligonucleotides are evaluated in animal models for their pharmacokinetic properties, biodistribution, and therapeutic efficacy in applications such as antisense therapy. The MOE modification enhances metabolic stability and reduces immunogenicity of therapeutic oligonucleotides. The compound has been used in VEGF-binding aptamers.
Enzyme Assay
For oligonucleotide synthesis, 2′-O-(2-Methoxyethyl)adenosine is converted to the corresponding phosphoramidite and incorporated into oligonucleotides using standard solid-phase synthesis protocols. Coupling efficiency is monitored by trityl cation release measurements at each synthesis cycle. After synthesis, the oligonucleotide is cleaved from the solid support and deprotected using appropriate reagents. The final modified oligonucleotide is purified by HPLC or PAGE and characterized by mass spectrometry.
Cell Assay
For cellular uptake and activity studies, cultured cells are treated with modified oligonucleotides containing 2′-O-(2-Methoxyethyl)adenosine. Cells are incubated with oligonucleotides for 24-72 hours, and cellular uptake is assessed by fluorescence microscopy or flow cytometry using fluorescently labeled oligonucleotides. For antisense applications, gene knockdown efficiency is evaluated by qRT-PCR or Western blot. For aptamer applications, binding to target proteins is assessed by surface plasmon resonance or ELISA.
Animal Protocol
For in vivo evaluation of modified oligonucleotides, mice or rats are administered the oligonucleotides via various routes. Pharmacokinetic parameters including half-life, clearance, and tissue distribution are determined by measuring oligonucleotide concentrations in plasma and tissues using hybridization-based assays or LC-MS. For therapeutic applications, efficacy is evaluated in appropriate disease models, with disease biomarkers or survival monitored over time.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2′-O-(2-Methoxyethyl)adenosine are typically characterized for the modified oligonucleotides incorporating this nucleoside. The MOE modification increases metabolic stability by reducing susceptibility to nuclease degradation. The compound has a molecular formula of C13H19N5O5 and a molecular weight of 325.32-325.33. It is a nucleoside analog used in oligonucleotide therapeutics. Detailed PK parameters depend on the specific oligonucleotide sequence and backbone chemistry.
Toxicity/Toxicokinetics
2′-O-(2-Methoxyethyl)adenosine is a research compound intended for laboratory use only and is not approved for human therapeutic use. As a modified nucleoside, it is used in the synthesis of oligonucleotides with enhanced properties for therapeutic and research applications. The MOE modification improves RNA target affinity and nuclease resistance. Standard laboratory safety precautions should be followed when handling this compound.
References

[1]. Chemo-enzymatic synthesis of 2'-O-methoxyethyl ribonucleosides using a phosphodiesterase from Serratia marcescens. Appl Microbiol Biotechnol. 2005;66(5):512-519./a >

Additional Infomation
2′-O-(2-Methoxyethyl)adenosine is a 2′-O-methoxyethyl derivative of adenosine with molecular formula C13H19N5O5 and molecular weight 325.32-325.33. It is used as a synthetic intermediate in oligonucleotide chemistry and has been used in VEGF-binding aptamers. The MOE modification improves RNA target affinity and nuclease resistance of therapeutic oligonucleotides. It is for research use only and has not been approved for clinical applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H19N5O5
Molecular Weight
325.32
Exact Mass
325.139
Elemental Analysis
C, 48.00; H, 5.89; N, 21.53; O, 24.59
CAS #
168427-74-5
PubChem CID
11393191
Appearance
White to off-white solid powder
Density
1.701g/cm3
Boiling Point
638.954ºC at 760 mmHg
Flash Point
340.227ºC
Vapour Pressure
0mmHg at 25°C
Index of Refraction
1.72
LogP
-0.7
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
6
Heavy Atom Count
23
Complexity
392
Defined Atom Stereocenter Count
4
SMILES
COCCO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O
InChi Key
PUDXUJRJLRLJIU-QYVSTXNMSA-N
InChi Code
InChI=1S/C13H19N5O5/c1-21-2-3-22-10-9(20)7(4-19)23-13(10)18-6-17-8-11(14)15-5-16-12(8)18/h5-7,9-10,13,19-20H,2-4H2,1H3,(H2,14,15,16)/t7-,9-,10-,13-/m1/s1
Chemical Name
(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-(2-methoxyethoxy)oxolan-3-ol
Synonyms
2'-O-(2-Methoxyethyl)adenosine; 2'-O-(2-Methoxyethyl)-adenosine; Adenosine, 2'-O-(2-methoxyethyl)-; 2'-MOE-Adenosine
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

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)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~768.5 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.39 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 (6.39 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
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 (6.39 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 3.0739 mL 15.3695 mL 30.7390 mL
5 mM 0.6148 mL 3.0739 mL 6.1478 mL
10 mM 0.3074 mL 1.5369 mL 3.0739 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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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:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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