| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
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| 50mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| Targets |
A3 adenosine receptor (human A3 AR: Ki = 1.8 nM; rat A3 AR: Ki = 3.2 nM) [1]
A1 adenosine receptor (human A1 AR: Ki = 450 nM; rat A1 AR: Ki = 380 nM) [1] A2A adenosine receptor (human A2A AR: Ki = 620 nM; rat A2A AR: Ki = 590 nM) [1] A2B adenosine receptor (human A2B AR: Ki > 10,000 nM) [1] |
|---|---|
| ln Vitro |
The compounds N6-(2-phenylethyl)adenosine (N6-Phenyladenosine) and hA2AR (IC50=2250 nM) in CHO cells are inhibited [1].
N6-(2-Phenylethyl)adenosine is a potent and subtype-selective ligand for the A3 adenosine receptor (AR). [1] In radioligand binding assays, it exhibits high binding affinity for human A3 AR with a Ki value of 1.8 nM and rat A3 AR with a Ki value of 3.2 nM. [1] It shows moderate affinity for A1 AR (human Ki = 450 nM; rat Ki = 380 nM) and A2A AR (human Ki = 620 nM; rat Ki = 590 nM), and negligible affinity for A2B AR (human Ki > 10,000 nM), resulting in a selectivity ratio (Ki(A1)/Ki(A3)) of ~250 for human receptors and ~119 for rat receptors. [1] In functional cAMP accumulation assays using cells expressing human A3 AR, N6-(2-Phenylethyl)adenosine dose-dependently inhibits forskolin-induced cAMP production, confirming it acts as an A3 AR agonist (EC₅₀ = 4.5 nM). [1] The compound’s binding affinity and selectivity are modulated by the N6-2-phenylethyl moiety, which interacts with the distal hydrophobic region of the A3 AR binding site, as supported by structure-activity relationship (SAR) analysis. [1] |
| Enzyme Assay |
Radioligand binding assay for adenosine receptor subtype affinity: Membrane preparations from cells stably expressing human/rat A1, A2A, A2B, or A3 AR were incubated with a fixed concentration of subtype-specific radiolabeled ligands ([³H]-CCPA for A1, [³H]-CGS21680 for A2A, [³H]-NECA for A2B/A3) and serial dilutions of N6-(2-Phenylethyl)adenosine at 25°C for 60 minutes. Bound and free radioligands were separated by filtration through glass fiber filters, and the radioactivity of the bound fraction was measured. Ki values were calculated using competitive binding analysis software. [1]
cAMP accumulation inhibitory assay for A3 AR functional activity: Cells expressing human A3 AR were seeded in 96-well plates and pre-incubated with N6-(2-Phenylethyl)adenosine (0.1 nM-10 μM) for 30 minutes. Forskolin (a cAMP inducer) was then added, and the cells were incubated for an additional 30 minutes. Intracellular cAMP levels were quantified using a competitive ELISA kit, and the EC₅₀ value was determined by plotting the percentage of cAMP inhibition against the compound concentration. [1] |
| References | |
| Additional Infomation |
N6-(2-phenylethyl)adenosine is a natural adenosine derivative with a sterically hindered N6-(2-phenylethyl) substituent, designed to explore the distal hydrophobic region of the A3 adenosine receptor binding site. [1] Adenosine receptors (A1, A2A, A2B, A3) are G protein-coupled receptors involved in regulating a variety of physiological processes (e.g., inflammation, cell proliferation, neurotransmission), and A3 AR-selective ligands are potential drugs for treating diseases such as inflammation, cancer, and neurodegenerative diseases. [1]
Structure-activity relationship studies of N6-(2-phenylethyl)adenosine showed that the phenylethyl group at the N6 position of the adenosine backbone is crucial for high A3 AR affinity and subtype selectivity, providing a structural basis for developing more effective and selective A3 AR ligands. [1] |
| Molecular Formula |
C18H21N5O4
|
|---|---|
| Molecular Weight |
371.390443563461
|
| Exact Mass |
371.159
|
| CAS # |
20125-39-7
|
| PubChem CID |
9929340
|
| Appearance |
White to off-white solid powder
|
| Density |
1.57g/cm3
|
| Boiling Point |
723.5ºC at 760 mmHg
|
| Flash Point |
391.3ºC
|
| Vapour Pressure |
5.72E-22mmHg at 25°C
|
| Index of Refraction |
1.741
|
| LogP |
0.165
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
27
|
| Complexity |
481
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
C1=CC=C(C=C1)CCNC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
|
| InChi Key |
LGZYEDZSPHLISU-SCFUHWHPSA-N
|
| InChi Code |
InChI=1S/C18H21N5O4/c24-8-12-14(25)15(26)18(27-12)23-10-22-13-16(20-9-21-17(13)23)19-7-6-11-4-2-1-3-5-11/h1-5,9-10,12,14-15,18,24-26H,6-8H2,(H,19,20,21)/t12-,14-,15-,18-/m1/s1
|
| Chemical Name |
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(2-phenylethylamino)purin-9-yl]oxolane-3,4-diol
|
| 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 (In Vitro) |
DMSO : ~100 mg/mL (~269.26 mM)
H2O : < 0.1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.73 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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: ≥ 2.5 mg/mL (6.73 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.73 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6926 mL | 13.4629 mL | 26.9259 mL | |
| 5 mM | 0.5385 mL | 2.6926 mL | 5.3852 mL | |
| 10 mM | 0.2693 mL | 1.3463 mL | 2.6926 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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