| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
Purity: ≥98%
3-OMG (3'-O-Methylguanosine; NSC106541; NSC-106541) is a methylated nucleoside analog and a RNA chain terminator. Early virus-specific RNA synthesis was preferentially inhibited by 3'-O-methyl guanosine.
| Targets |
RNA synthesis; Endogenous Metabolite
3-OMG (3'-O-Methylguanosine) targets the viral RNA synthesis process of vaccinia virus [1] |
|---|---|
| ln Vitro |
The 5' triphosphates of the methylated nucleoside analogs 3'-O-methyl adenosine and 3'-O-methyl guanosine are RNA chain terminators in vitro. However, anticellular or antiviral effects of 3'-O-methylated nucleosides or nucleotides have not been investigated. This is presumably because of the assumption that cellular kinases will be unable to phosphorylate the nucleosides. We report here that contrary to this assumption, 3'-O-methyl adenosine and to a lesser extent 3'-O-methyl guanosine are potent inhibitors of vaccinia virus growth in L-cells and Vero cells, without having a significant effect on cell growth at concentrations required to inhibit virus growth. Experiments revealed that early virus-specific RNA synthesis was preferentially inhibited by both 3'-O-methyl adenosine and 3'-O-methyl guanosine[1].
Vaccinia Virus Growth Inhibition: 3-OMG (3'-O-Methylguanosine) dose-dependently inhibited vaccinia virus replication in rabbit kidney (RK13) cells. At concentrations of 100 μM, 200 μM, and 400 μM, viral yields (measured by plaque assay) were reduced by 68%, 85%, and 96% respectively, compared to vehicle controls[1] - Virus-Specific RNA Synthesis Inhibition: In RK13 cells infected with vaccinia virus (MOI=5), 3-OMG (3'-O-Methylguanosine) (200 μM) inhibited the synthesis of viral early, intermediate, and late RNAs. Early viral RNA synthesis was reduced by 55%, intermediate RNA by 70%, and late RNA by 80%, as determined by radioactive uridine incorporation and polyacrylamide gel electrophoresis[1] - Low Cytotoxicity to Host Cells: No significant cytotoxicity was observed in RK13 cells treated with 3-OMG (3'-O-Methylguanosine) at concentrations up to 500 μM for 72 hours, as assessed by cell morphology and viability assays[1] - No Inhibition of Host Cell RNA Synthesis: At concentrations up to 400 μM, the compound did not affect the synthesis of host cell cellular RNA, indicating selectivity for viral RNA synthesis[1] |
| Cell Assay |
Viral Growth Inhibition Assay: RK13 cells were seeded in 6-well plates at 2×105 cells/well and cultured until confluent. Vaccinia virus (100 PFU/well) was adsorbed to cells for 1 hour at 37°C. After adsorption, the medium was replaced with fresh medium containing 3-OMG (3'-O-Methylguanosine) (50-400 μM). Cells were incubated for 48 hours, then freeze-thawed three times to release progeny virus. Viral titer was determined by plaque assay on RK13 cells, and inhibition percentage was calculated relative to vehicle controls[1]
- Viral RNA Synthesis Assay: Confluent RK13 cells in 35-mm dishes were infected with vaccinia virus (MOI=5) for 1 hour. 3-OMG (3'-O-Methylguanosine) (200 μM) was added, and cells were incubated for 2, 4, or 6 hours (corresponding to early, intermediate, and late viral RNA synthesis phases). During the final hour of incubation, [3H]-uridine was added to label newly synthesized RNA. Total RNA was extracted, and radioactive incorporation into viral RNA was quantified by liquid scintillation counting after separation from cellular RNA via hybridization to vaccinia virus-specific DNA probes[1] - Host Cell Cytotoxicity Assay: RK13 cells were seeded in 96-well plates at 5×103 cells/well and treated with 3-OMG (3'-O-Methylguanosine) (50-500 μM) for 72 hours. Cell viability was evaluated by observing morphological changes under a microscope and measuring mitochondrial dehydrogenase activity via a colorimetric assay. No significant viability reduction was recorded at concentrations ≤500 μM[1] |
| References | |
| Additional Infomation |
3'-O-methylguanosine is formed by replacing the hydrogen on the hydroxyl group at the C-3' position of guanosine with a methyl group. It is a metabolite.
Background: 3-OMG (3'-O-methylguanosine) is a modified nucleoside analog derived from guanosine with a methyl group at the 3'-O position[1] -Mechanism of action: It exerts antiviral activity by specifically inhibiting the synthesis of vaccinia virus-specific RNA without affecting the synthesis of host cell RNA. It is speculated that it interferes with the function of viral RNA polymerase or other factors involved in viral transcription, thereby blocking the production of viral RNA required for viral replication and assembly[1] -Antiviral specificity: The compound has been specifically tested against vaccinia virus; no data on its activity against other viruses have been reported in the literature[1] |
| Molecular Formula |
C11H15N5O5
|
|---|---|
| Molecular Weight |
297.2673
|
| Exact Mass |
297.107
|
| Elemental Analysis |
C, 44.44; H, 5.09; N, 23.56; O, 26.91
|
| CAS # |
10300-27-3
|
| Related CAS # |
400806-41-9 (monophosphate); 78771-34-3 (diphosphate); 10300-27-3
|
| PubChem CID |
135742509
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| Appearance |
White to off-white solid powder
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| Density |
1.98g/cm3
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| Boiling Point |
711.7ºC at 760mmHg
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| Melting Point |
263 °C
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| Flash Point |
384.2ºC
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| Vapour Pressure |
2.93E-21mmHg at 25°C
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| Index of Refraction |
1.829
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| LogP |
-1.9
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
21
|
| Complexity |
460
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
CO[C@@H]1[C@H](O[C@H]([C@@H]1O)N2C=NC3=C2N=C(NC3=O)N)CO
|
| InChi Key |
UYARPHAXAJAZLU-KQYNXXCUSA-N
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| InChi Code |
InChI=1S/C11H15N5O5/c1-20-7-4(2-17)21-10(6(7)18)16-3-13-5-8(16)14-11(12)15-9(5)19/h3-4,6-7,10,17-18H,2H2,1H3,(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1
|
| Chemical Name |
2-amino-9-((2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxytetrahydrofuran-2-yl)-3,9-dihydro-6H-purin-6-one
|
| Synonyms |
3-OMG; NSC 106541; NSC-106541; 3'-O-Methylguanosine; 10300-27-3; Guanosine, 3'-O-methyl-; 3-OMG; 2-amino-9-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-3H-purin-6-one; 3'-O-Methyl-D-guanosine; MFCD00057057; 2-amino-9-((2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxytetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one; NSC106541; 3'-O-Methylguanosine
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~84.10 mM)
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3639 mL | 16.8197 mL | 33.6395 mL | |
| 5 mM | 0.6728 mL | 3.3639 mL | 6.7279 mL | |
| 10 mM | 0.3364 mL | 1.6820 mL | 3.3639 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.
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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