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LNA-Adenosine

Alias: LNA-A; LNA Adenosine; LNA-Adenosine
Cat No.:V17905 Purity: ≥98%
2'-O,4'-C-Methyleneadenosine (LNA-A) is a locked nucleic acid and an adenosine analog.
LNA-Adenosine
LNA-Adenosine Chemical Structure CAS No.: 206055-70-1
Product category: New1
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,4'-C-Methyleneadenosine (LNA-A) is a locked nucleic acid and an adenosine analog.
LNA-Adenosine (CAS#: 206055-70-1), also known as 2'-O,4'-C-Methyleneadenosine, is a locked nucleic acid (LNA) and an adenosine analog. It is a synthetic nucleoside analog where the ribose moiety is locked in a conformation that enhances binding affinity to complementary RNA and increases stability against nuclease degradation. LNA-A serves as a critical building block for antisense oligonucleotides (ASOs), splice-switching oligos, aptamers, and diagnostic probes where enhanced target binding, nuclease resistance, and mismatch discrimination are required. Its application extends to antisense oligonucleotide design and RNA interference studies, making it essential for researchers exploring RNA-related therapies and molecular diagnostics. When metabolized to its triphosphate form (LNA-ATP), LNA-Adenosine can act as a competitive inhibitor of viral RNA-dependent RNA polymerases (RdRp).
Biological Activity I Assay Protocols (From Reference)
Targets
LNA-Adenosine does not have a specific biological target like an enzyme or receptor. As a locked nucleic acid and adenosine analog, its primary application is in nucleic acid chemistry and as a building block for oligonucleotides. It can be incorporated into DNA or RNA sequences to increase their binding affinity and stability. Oligonucleotides modified with LNA units display greatly increased affinity toward nucleic acid targets, improved binding specificity, and enhanced enzymatic stability relative to unmodified strands. When metabolized to its triphosphate form (LNA-ATP), it can act as a competitive inhibitor of viral RNA-dependent RNA polymerases (RdRp).
ln Vitro
LNA-Adenosine, as a nucleoside analog, can exhibit antiviral activity. It shows an EC50 of >50 μM against wild-type Hepatitis C virus genotype 1b in human HuH7 cells. Its primary in vitro activity is related to its incorporation into nucleic acids, where it enhances stability and target binding affinity. LNA-Adenosine exhibits increased stability and binding affinity for complementary RNA sequences. Oligonucleotides modified with LNA units display greatly increased affinity toward nucleic acid targets, improved binding specificity, and enhanced enzymatic stability relative to unmodified strands.
ln Vivo
In vivo activity for LNA-Adenosine is not typically evaluated as a standalone therapeutic agent. Its effects are studied in the context of LNA-modified oligonucleotides, which can be used for various in vivo applications such as gene silencing or as aptamers. The LNA modification improves the pharmacokinetic properties of these oligonucleotides. 2'-O-methyl/locked nucleic acid (LNA) mixmer antisense oligonucleotides are potent and selective inhibitors of RNA editing on two different target RNAs.
Enzyme Assay
Specific protocols for enzyme/receptor binding assays for LNA-Adenosine are not applicable. As a nucleic acid analog, its interactions are studied in the context of hybridization to complementary RNA or DNA strands, often measured by melting temperature (Tm) assays to determine binding affinity. LNA-Adenosine exhibits increased stability and binding affinity for complementary RNA sequences.
Cell Assay
Cellular assays for LNA-Adenosine are typically conducted by incorporating it into oligonucleotides and studying their effects in cell-based systems. For example, its antiviral activity can be assessed in cells infected with a virus, such as the HCV assay in HuH7 cells where an EC50 of >50 μM was determined. 2'-O-methyl/locked nucleic acid (LNA) mixmer antisense oligonucleotides are potent and selective inhibitors of RNA editing on two different target RNAs.
Animal Protocol
In vivo studies for LNA-Adenosine are not conducted as a single agent. Instead, LNA-modified oligonucleotides are administered to animal models to study their therapeutic efficacy, pharmacokinetics, and biodistribution. The LNA modification enhances the stability and potency of these oligonucleotides in vivo. 2'-O-methyl/locked nucleic acid (LNA) mixmer antisense oligonucleotides are potent and selective inhibitors of RNA editing on two different target RNAs.
ADME/Pharmacokinetics
Specific pharmacokinetic data for LNA-Adenosine is not available. As a building block for oligonucleotides, its PK properties are not typically evaluated. However, LNA-modified oligonucleotides generally have improved pharmacokinetic properties, including increased stability against nucleases and longer half-lives.
Toxicity/Toxicokinetics
Specific toxicological data for LNA-Adenosine is not available. As a research chemical, its safety profile is not well-characterized. Standard safety precautions for handling nucleic acid analogs should be followed.
References

[1]. Design, synthesis, and biological evaluation of LNA nucleosides as adenosine A3 receptor ligands. Bioorg Med Chem. 2007 Aug 15;15(16):5440-7.

Additional Infomation
LNA-Adenosine is a research tool for nucleic acid chemistry and oligonucleotide-based therapeutics. It is not approved for clinical use. The locked nucleic acid modification enhances the stability and target binding affinity of oligonucleotides, making it a valuable tool for antisense, siRNA, and aptamer technologies. LNA-A serves as a critical building block for antisense oligonucleotides (ASOs), splice-switching oligos, aptamers, and diagnostic probes where enhanced target binding, nuclease resistance, and mismatch discrimination are required.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H13N5O4
Molecular Weight
279.26
Exact Mass
279.096
CAS #
206055-70-1
PubChem CID
44436074
Appearance
White to off-white solid powder
Density
2.1±0.1 g/cm3
Boiling Point
660.0±65.0 °C at 760 mmHg
Flash Point
352.9±34.3 °C
Vapour Pressure
0.0±2.1 mmHg at 25°C
Index of Refraction
1.953
LogP
0.41
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
2
Heavy Atom Count
20
Complexity
401
Defined Atom Stereocenter Count
4
SMILES
C1[C@]2([C@H]([C@@H](O1)[C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)CO
InChi Key
GHKDRNDFVCEETA-KYAGDKKUSA-N
InChi Code
InChI=1S/C11H13N5O4/c12-8-5-9(14-3-13-8)16(4-15-5)10-6-7(18)11(1-17,20-10)2-19-6/h3-4,6-7,10,17-18H,1-2H2,(H2,12,13,14)/t6-,7+,10-,11+/m1/s1
Chemical Name
(1S,3R,4R,7S)-3-(6-aminopurin-9-yl)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-7-ol
Synonyms
LNA-A; LNA Adenosine; LNA-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)
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 3.5809 mL 17.9045 mL 35.8089 mL
5 mM 0.7162 mL 3.5809 mL 7.1618 mL
10 mM 0.3581 mL 1.7904 mL 3.5809 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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