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2'-C-methyluridine (1-(2-C-methyl-β-D-ribofuranosyl)uracil)

Cat No.:V55273 Purity: ≥98%
2'-C-methyluridine is a uridine analog.
2'-C-methyluridine (1-(2-C-methyl-β-D-ribofuranosyl)uracil)
2'-C-methyluridine (1-(2-C-methyl-β-D-ribofuranosyl)uracil) Chemical Structure CAS No.: 31448-54-1
Product category: Nucleoside Antimetabolite/Analog
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
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Product Description
2'-C-methyluridine is a uridine analog. Uridine has potential antiepileptic effects and its analogues may be utilized to study anticonvulsant (antiepileptic/antiseizure) and anxiolytic activity and to develop new antihypertensive agents.
2'-C-methyluridine (CAS 31448-54-1) is a nucleoside analog derived from uridine, in which a methyl group is attached to the 2' carbon of the ribose sugar. Its molecular formula is C10H14N2O6 with a molecular weight of 258.23 g/mol. This compound is a uridine analog and is a key intermediate in the synthesis of methylcytidine. It shows HCV polymerase inhibitory activity and is used in the synthesis of Sofosbuvir.
Biological Activity I Assay Protocols (From Reference)
Targets
2'-C-methyluridine targets HCV polymerase (NS5B), the enzyme responsible for hepatitis C virus RNA replication. The compound is a uridine analog that can inhibit HCV polymerase activity. Uridine has potential antiepileptic effects and its analogs may be used to study anticonvulsant and anxiolytic activities.
ln Vitro
In cell-free biochemical systems, 2'-C-methyluridine exhibits HCV polymerase inhibitory activity. The compound inhibits the polymerase activity of the HCV NS5B enzyme, preventing viral RNA replication. This activity makes the compound valuable for the development of anti-HCV therapeutics.
ln Vivo
In cell-based assays, 2'-C-methyluridine may inhibit HCV replication in infected cells. As a uridine analog, the compound may also have effects on cellular uridine metabolism. The compound is used as a key intermediate in the synthesis of methylcytidine and Sofosbuvir.
Enzyme Assay
The cell-free HCV polymerase assay involves incubation of purified HCV NS5B polymerase with RNA template, NTPs (including labeled nucleotides), and the compound at various concentrations. The reaction is incubated at 37°C, and RNA synthesis is measured by incorporation of labeled nucleotides. The IC50 is determined from dose-response curves.
Cell Assay
Cell-based assays for anti-HCV activity involve culturing HCV replicon cells or virus-infected cells and treating them with 2'-C-methyluridine at concentrations ranging from 0.1 to 100 μM. HCV replication is assessed by measuring HCV RNA levels by qRT-PCR or by measuring viral protein expression. The compound's effects on cellular uridine metabolism can also be assessed.
Animal Protocol
There is no established animal experimental protocol for 2'-C-methyluridine specifically. As a nucleoside analog with anti-HCV activity, the compound could potentially be evaluated in animal models of HCV infection. The compound is also used in the synthesis of Sofosbuvir, which has been extensively studied in animal models.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2'-C-methyluridine have not been extensively reported. As a small molecule with molecular weight of 258.23 g/mol, the compound would be expected to have reasonable bioavailability and tissue penetration. The compound is used as a key intermediate in the synthesis of Sofosbuvir, which has well-characterized pharmacokinetic properties.
Toxicity/Toxicokinetics
Toxicity data for 2'-C-methyluridine are not well documented. As a nucleoside analog, the compound may have effects on normal cells as well as virus-infected cells. Standard toxicity studies would be required to determine the safety profile.
References

[1]. Uridine and its nucleotides: biological actions, therapeutic potentials. Trends Pharmacol Sci. 1999 May;20(5):218-25.

Additional Infomation
2'-C-methyluridine is a research compound used as a key intermediate in the synthesis of methylcytidine类药物 and Sofosbuvir, an FDA-approved drug for hepatitis C treatment. The compound exhibits HCV polymerase inhibitory activity. It is a uridine analog and is classified as a 2'-C-methyl nucleoside. This product is intended for research and manufacturing use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H14N2O6
Molecular Weight
258.23
Exact Mass
258.085
CAS #
31448-54-1
PubChem CID
500903
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Melting Point
110-112ºC
Index of Refraction
1.615
LogP
-0.85
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
2
Heavy Atom Count
18
Complexity
411
Defined Atom Stereocenter Count
4
SMILES
C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O)O
InChi Key
NBKORJKMMVZAOZ-VPCXQMTMSA-N
InChi Code
InChI=1S/C10H14N2O6/c1-10(17)7(15)5(4-13)18-8(10)12-3-2-6(14)11-9(12)16/h2-3,5,7-8,13,15,17H,4H2,1H3,(H,11,14,16)/t5-,7-,8-,10-/m1/s1
Chemical Name
1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-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)
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 3.8725 mL 19.3626 mL 38.7252 mL
5 mM 0.7745 mL 3.8725 mL 7.7450 mL
10 mM 0.3873 mL 1.9363 mL 3.8725 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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