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2′-O-Methyl-8-methyl guanosine

Cat No.:V47549 Purity: ≥98%
2'-O-Methyl-8-methyl guanosine (m8Gm) is a Z-type RNA stabilizer.
2′-O-Methyl-8-methyl guanosine
2′-O-Methyl-8-methyl guanosine Chemical Structure CAS No.: 2306782-64-7
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
Official Supplier of:
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Product Description
2'-O-Methyl-8-methyl guanosine (m8Gm) is a Z-type RNA stabilizer. 2'-O-Methyl-8-methyl guanosine significantly stabilizes Z-DNA under low-salt conditions. m8Gm-containing oligonucleotides stabilize Z-DNA under low-salt conditions.
2'-O-Methyl-8-methyl guanosine (2306782-64-7, m8Gm) is a chemically modified nucleoside with methylation at the 8-position and an O-methyl group at the 2' position. It is a Z-form RNA stabilizer that can markedly stabilize Z-RNA at low salt conditions. Oligonucleotides containing m8Gm can stabilize Z-DNA under low-salt conditions, making it valuable for structural biology and nucleic acid research.
Biological Activity I Assay Protocols (From Reference)
Targets
Target: Z-form RNA/DNA structures (chemical probe). 2'-O-Methyl-8-methyl guanosine (m8Gm) is not a classical drug with a protein target; instead, it is a modified nucleoside that stabilizes non-canonical Z-form nucleic acid structures. It promotes and stabilizes Z-RNA and Z-DNA by favoring the syn conformation of the glycosidic bond, facilitating the alternating syn-anti backbone pattern characteristic of Z-form helices.
ln Vitro
In vitro, 2'-O-Methyl-8-methyl guanosine (m8Gm) stabilizes Z-RNA under low-salt conditions, enabling the study of Z-form nucleic acid structures. Oligonucleotides containing m8Gm exhibit increased Z-DNA stability in low-salt buffers (e.g., 10-50 mM NaCl), whereas natural nucleic acids require high salt concentrations (∼2 M NaCl) to adopt Z-form. No direct pharmacological activity (cell viability, enzyme inhibition) is reported.
ln Vivo
No in vivo studies have been performed with 2'-O-Methyl-8-methyl guanosine. This compound is not intended for in vivo administration for therapeutic purposes; it is a research tool for studying nucleic acid structure and function in cell-free systems. Its potential applications in vivo (e.g., as an antisense oligonucleotide modification) have not been explored.
Enzyme Assay
For cell-free Z-RNA stabilization assays: Z-RNA-forming oligonucleotides (e.g., repeating CG sequences, d(CG)n) are synthesized with m8Gm incorporated at specific positions. Oligonucleotides are dissolved in low-salt buffer (e.g., 10-50 mM NaCl, 5 mM Tris-HCl, pH 7.5) at 10-100 uM. CD (circular dichroism) spectroscopy is performed to monitor the transition from B-form (positive peak at ∼275 nm, negative peak at ∼210 nm) to Z-form (negative peak at ∼290 nm, positive peak at ∼210 nm) upon addition of the oligonucleotide to buffer. UV absorbance at 254 nm and 295 nm can also measure Z-form stability.
Cell Assay
No cell-based assays are performed with this compound, as it is a nucleoside used for chemical synthesis of modified oligonucleotides, not a compound that is directly added to cells for biological activity studies. Modified oligonucleotides containing m8Gm may be transfected into cells for gene regulation studies, but the nucleoside itself is not used in cell culture. No specific cell-based protocols have been reported.
Animal Protocol
No animal studies are conducted with 2'-O-Methyl-8-methyl guanosine. The compound is not administered to animals. It is used exclusively as a building block for the synthesis of modified oligonucleotides for in vitro structural studies or as a research reagent in nucleic acid chemistry. No in vivo efficacy or safety studies have been performed.
ADME/Pharmacokinetics
PK properties are not applicable for this compound, as it is not intended for in vivo administration as a drug. As a modified nucleoside (MW 311.29), if administered systemically, it would likely be rapidly metabolized by nucleoside phosphorylases or incorporated into nucleic acids, but no PK studies have been performed. The compound is for research use only and is not a drug candidate.
Toxicity/Toxicokinetics
No toxicity data are available for this compound. As a modified nucleoside, it is not cytotoxic at concentrations used in oligonucleotide synthesis. The compound is for research use only and is not intended for human therapeutic administration. It is considered non-hazardous for transport under normal laboratory conditions. Not for human consumption.
References

[1]. Balasubramaniyam T, Ishizuka T, Xiao CD, Bao HL, Xu Y. 2'-O-Methyl-8-methylguanosine as a Z-Form RNA Stabilizer for Structural and Functional Study of Z-RNA. Molecules. 2018;23(10):2572.

[2]. Balasubramaniyam T, Ishizuka T, Xu Y. Stability and properties of Z-DNA containing artificial nucleobase 2'-O-methyl-8-methyl guanosine. Bioorg Med Chem. 2019;27(2):364-369.

Additional Infomation
2'-O-Methyl-8-methyl guanosine is a research reagent, not a drug. It is not FDA-approved for clinical use. It is used in nucleic acid chemistry and structural biology to study Z-form DNA and RNA conformations. It is also used to increase the stability of oligonucleotides for potential antisense or siRNA applications, and as a tool for investigating the biological roles of Z-nucleic acids in gene regulation, inflammation, and immunity.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H17N5O5
Molecular Weight
311.293882131577
Exact Mass
311.122
CAS #
2306782-64-7
PubChem CID
137249367
Appearance
White to off-white solid powder
LogP
-1
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
3
Heavy Atom Count
22
Complexity
489
Defined Atom Stereocenter Count
4
SMILES
O1[C@H](CO)[C@H]([C@H]([C@@H]1N1C(C)=NC2C(NC(=N)N=C12)=O)OC)O
InChi Key
VKBDRYNPOJCCAX-IOSLPCCCSA-N
InChi Code
InChI=1S/C12H17N5O5/c1-4-14-6-9(15-12(13)16-10(6)20)17(4)11-8(21-2)7(19)5(3-18)22-11/h5,7-8,11,18-19H,3H2,1-2H3,(H3,13,15,16,20)/t5-,7-,8-,11-/m1/s1
Chemical Name
2-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-8-methyl-1H-purin-6-one
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 3.2124 mL 16.0622 mL 32.1244 mL
5 mM 0.6425 mL 3.2124 mL 6.4249 mL
10 mM 0.3212 mL 1.6062 mL 3.2124 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

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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:
  • 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.

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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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