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2'-O-MOE-5MeU-3'-phosphoramidite (2'-O-MOE-5-ME-U phosphoramidite monomer)

Alias: 2'-O-MOE-5-ME-U phosphoramidite monomer; 2'-O-MOE-5-ME-U phosphoramidite monomer
2'-O-MOE-5MeU-3'-phosphoramidite is a phosphoramidite monomer that may be utilized in the preparation /synthesis of oligonucleotides.
2'-O-MOE-5MeU-3'-phosphoramidite (2'-O-MOE-5-ME-U phosphoramidite monomer)
2'-O-MOE-5MeU-3'-phosphoramidite (2'-O-MOE-5-ME-U phosphoramidite monomer) Chemical Structure CAS No.: 163878-63-5
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
Official Supplier of:
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Product Description
2'-O-MOE-5MeU-3'-phosphoramidite is a phosphoramidite monomer that may be utilized in the preparation /synthesis of oligonucleotides.
2'-O-MOE-5MeU-3'-phosphoramidite (CAS 163878-63-5) is a second-generation 2'-O-methoxyethyl (2'-MOE) modified nucleoside phosphoramidite monomer used in the automated solid-phase synthesis of antisense oligonucleotides (ASOs) and therapeutic nucleic acids. The compound features a 2'-O-methoxyethyl modification, a 5-methyluracil base, and a 3'-phosphoramidite functionality. Its molecular formula is C43H55N4O10P with a molecular weight of 818.89 g/mol. This monomer is classified as a nucleotide analog and is utilized in nucleic acid chemistry research.
Biological Activity I Assay Protocols (From Reference)
Targets
As a chemical reagent for oligonucleotide synthesis, 2'-O-MOE-5MeU-3'-phosphoramidite does not have a defined biological target. Its purpose is to serve as a building block for incorporating 2'-O-methoxyethyl-5-methyluridine residues into synthetic oligonucleotides. The 2'-MOE modification is one of the most widely used chemical modifications in therapeutic antisense oligonucleotides, providing enhanced nuclease resistance, improved binding affinity, and reduced immune stimulation.
ln Vitro
In cell-free biochemical systems, this phosphoramidite monomer is incorporated into oligonucleotide sequences during solid-phase synthesis. The resulting modified oligonucleotides containing 2'-MOE-5-methyluridine residues exhibit significantly enhanced stability against nuclease degradation and improved binding affinity to complementary RNA sequences. These properties make the monomer essential for the preparation of second-generation antisense oligonucleotides with improved therapeutic properties.
ln Vivo
This compound does not exhibit direct cellular activity as it is a chemical synthesis reagent rather than a bioactive molecule. Oligonucleotides synthesized using this monomer can be delivered into cells for various functional studies. The 2'-MOE modification enhances the metabolic stability and reduces the immune stimulatory potential of oligonucleotides in cellular environments. Antisense oligonucleotides containing 2'-MOE modifications are widely used for gene silencing applications. Cellular uptake typically occurs through endocytosis.
Enzyme Assay
The standard procedure for incorporating this phosphoramidite involves solid-phase oligonucleotide synthesis using standard phosphoramidite chemistry. The monomer is dissolved in anhydrous acetonitrile at 0.1 M concentration and coupled to the growing oligonucleotide chain using activator solutions such as tetrazole or 5-ethylthio-1H-tetrazole. Coupling times typically range from 2-5 minutes. Following chain assembly, the oligonucleotide is deprotected using ammonium hydroxide treatment to remove protecting groups.
Cell Assay
No cell-based experimental protocols are directly applicable to this phosphoramidite monomer as it is a chemical synthesis reagent. Oligonucleotides containing 2'-MOE-5-methyluridine residues synthesized using this monomer can be evaluated in cell culture experiments. Typical protocols include transfection of modified ASOs into mammalian cell lines at concentrations of 10-100 nM using lipid-based transfection reagents or gymnotic delivery. Cells are incubated for 24-72 hours, and target gene knockdown is assessed by qRT-PCR or Western blotting.
Animal Protocol
2'-O-MOE-5MeU-3'-phosphoramidite is not administered to animals as it is a chemical intermediate for oligonucleotide synthesis. Oligonucleotides containing 2'-MOE-5-methyluridine residues synthesized using this monomer are widely evaluated in animal models for therapeutic applications. Typical studies involve administration of modified ASOs to mice or rats via intravenous or subcutaneous routes at doses of 1-50 mg/kg. Pharmacodynamic endpoints include target gene silencing in tissues and therapeutic efficacy in disease models.
ADME/Pharmacokinetics
As a chemical reagent, this compound does not have established pharmacokinetic properties. Oligonucleotides containing 2'-MOE modifications exhibit significantly enhanced metabolic stability compared to unmodified or first-generation phosphorothioate oligonucleotides. The 2'-MOE modification increases resistance to nuclease degradation, resulting in plasma half-lives of several days. Biodistribution is predominantly to liver, kidney, and spleen. These properties have made 2'-MOE-modified ASOs successful in clinical development.
Toxicity/Toxicokinetics
The compound is not intended for therapeutic use and lacks established toxicity profiles. Standard laboratory safety precautions should be observed when handling this chemical reagent. Oligonucleotides containing 2'-MOE modifications generally exhibit improved safety profiles with reduced immune stimulation and hepatotoxicity compared to earlier generations of oligonucleotides. However, potential toxicities include injection site reactions, complement activation, and renal effects at high doses.
Additional Infomation
2'-O-MOE-5MeU-3'-phosphoramidite is a research-grade chemical supplied for oligonucleotide synthesis applications. It is not an approved pharmaceutical and has no clinical trial history as a standalone compound. The 2'-MOE modification is one of the most successful chemical modifications in therapeutic oligonucleotides, with multiple FDA-approved ASO drugs incorporating this chemistry. The compound is typically stored at -20°C under desiccated conditions. This product is for research use only and is not for human therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C43H55N4O10P
Molecular Weight
818.89
Exact Mass
818.366
CAS #
163878-63-5
PubChem CID
92043625
Appearance
White to off-white solid powder
LogP
6.461
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
21
Heavy Atom Count
58
Complexity
1340
Defined Atom Stereocenter Count
4
SMILES
CC1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OP(N(C(C)C)C(C)C)OCCC#N)OCCOC
InChi Key
YFRRKZDUDXHJNC-KZQAAKLLSA-N
InChi Code
InChI=1S/C43H55N4O10P/c1-29(2)47(30(3)4)58(55-24-12-23-44)57-38-37(56-41(39(38)53-26-25-50-6)46-27-31(5)40(48)45-42(46)49)28-54-43(32-13-10-9-11-14-32,33-15-19-35(51-7)20-16-33)34-17-21-36(52-8)22-18-34/h9-11,13-22,27,29-30,37-39,41H,12,24-26,28H2,1-8H3,(H,45,48,49)/t37-,38-,39-,41-,58?/m1/s1
Chemical Name
3-[[(2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
Synonyms
2'-O-MOE-5-ME-U phosphoramidite monomer; 2'-O-MOE-5-ME-U phosphoramidite monomer
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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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)
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2212 mL 6.1058 mL 12.2117 mL
5 mM 0.2442 mL 1.2212 mL 2.4423 mL
10 mM 0.1221 mL 0.6106 mL 1.2212 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
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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