| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
2-Methyladenosine targets a range of cellular proteins and enzymes. As an adenosine analog, it can interact with adenosine receptors (A1, A2A, A2B, A3) and be a substrate for enzymes involved in purine metabolism, such as adenosine deaminase (ADA). It can also be phosphorylated by cellular kinases to its monophosphate and triphosphate forms, where the latter can act as a chain terminator for DNA/RNA polymerases.
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|---|---|
| ln Vitro |
In vitro, 2-Methyladenosine demonstrates selective and potent activity against Mycobacterium tuberculosis, including its persistent, non-replicating forms. As an adenosine analog, it inhibits cancer progression by interfering with DNA synthesis and inducing apoptosis. Its antiproliferative effects are leveraged in research settings to study nucleoside metabolism and signaling pathways in various cell lines.
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| ln Vivo |
Specific in vivo data for 2-Methyladenosine is not provided in the literature, but its activity against M. tuberculosis suggests potential for in vivo efficacy. An adenosine analog with good bioavailability could be administered in animal models to evaluate its effects on vasodilation (by acting on adenosine receptors) or to test its potential as an anti-tuberculosis agent, assessing its ability to reduce bacterial load in infected lungs.
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| Enzyme Assay |
For a cell-free system, the affinity of 2-Methyladenosine for adenosine receptors can be measured by competitive radioligand binding assays. Membrane preparations from cells expressing the receptor are incubated with a radiolabeled adenosine agonist (e.g., [3H]-NECA) and increasing concentrations of 2-Methyladenosine. The reduction in radioligand binding is measured by scintillation counting to calculate the Ki.
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| Cell Assay |
In cellular assays, immune or cancer cells are cultured and treated with serial dilutions of 2-Methyladenosine. For tuberculosis research, infected macrophages are treated with the compound, and the bacterial burden is measured by CFU (colony-forming unit) counts after several days. To assess its role in cancer, cell viability is measured by MTT or CellTiter-Glo, and apoptosis is detected by flow cytometry.
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| Animal Protocol |
For an in vivo study to assess tuberculosis activity, 2-Methyladenosine would be formulated in a vehicle such as PBS and administered to infected mice via intraperitoneal (IP) injection. The mice would be treated daily for several weeks. At the end of the study, the animals are euthanized, and the bacterial load in the lungs and spleen is quantified by CFU to assess the compound's efficacy.
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| ADME/Pharmacokinetics |
Specific ADME data for 2-Methyladenosine is not provided. As a nucleoside analog, it is expected to be water-soluble. Its stability in plasma is influenced by the presence of adenosine deaminase (ADA), which deaminates adenosine analogs, potentially shortening its half-life. Modifications like the 2-methyl group can alter its susceptibility to such metabolic enzymes.
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| Toxicity/Toxicokinetics |
No specific toxicology data for 2-Methyladenosine is presented. As an adenosine analog, its toxicity profile would likely be related to its mechanism of action. For example, potent activation of adenosine receptors can lead to cardiovascular effects like hypotension and bradycardia. Its safety profile for any therapeutic use would need to be carefully established in preclinical studies.
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| References | |
| Additional Infomation |
2-Methyladenosine is a methyladenosine in which the methyl group is located at the 2-position of the adenine ring.
See also: 2-O-methyladenosine (note moved to). The methyl substitution at the C2 position of adenosine is a common strategy in medicinal chemistry to modulate the binding affinity and selectivity for different adenosine receptors. It also imparts resistance to metabolism by adenosine deaminase. 2-Methyladenosine serves as a valuable reference compound for studying the structure-activity relationships (SAR) of adenosine receptor ligands and nucleoside antimetabolites. It is a preclinical research tool. |
| Molecular Formula |
C11H15N5O4
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|---|---|
| Molecular Weight |
281.27
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| Exact Mass |
281.112
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| CAS # |
16526-56-0
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| PubChem CID |
459890
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| Appearance |
White to off-white solid powder
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| Density |
1.96g/cm3
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| Boiling Point |
517.8ºC at 760mmHg
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| Flash Point |
266.9ºC
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| Vapour Pressure |
1.51E-11mmHg at 25°C
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| Index of Refraction |
1.856
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| LogP |
-0.6
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
20
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| Complexity |
362
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| Defined Atom Stereocenter Count |
4
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| SMILES |
OC[C@H]1O[C@@H](N2C=NC3=C(N=C(N=C23)C)N)[C@H](O)[C@@H]1O
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| InChi Key |
IQZWKGWOBPJWMX-IOSLPCCCSA-N
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| InChi Code |
InChI=1S/C11H15N5O4/c1-4-14-9(12)6-10(15-4)16(3-13-6)11-8(19)7(18)5(2-17)20-11/h3,5,7-8,11,17-19H,2H2,1H3,(H2,12,14,15)/t5-,7-,8-,11-/m1/s1
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| Chemical Name |
(2R,3R,4S,5R)-2-(6-amino-2-methylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
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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 |
| 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: ~6.3 mg/mL (~22.2 mM; with ultrasonication)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.62 mg/mL (2.20 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (6.2 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.62 mg/mL (2.20 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (6.2 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5553 mL | 17.7765 mL | 35.5530 mL | |
| 5 mM | 0.7111 mL | 3.5553 mL | 7.1106 mL | |
| 10 mM | 0.3555 mL | 1.7777 mL | 3.5553 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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