| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Adenosine receptors; DNA synthesis pathways. As an adenosine analog, 2',3'-O-Isopropylideneadenosine exerts its biological effects primarily through adenosine receptor-mediated pathways. Adenosine analogs mostly act as smooth muscle vasodilators and have also been shown to inhibit cancer progression. The compound may interfere with nucleic acid metabolism when deprotected. The purine base adenine is crucial for its biological activity.
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|---|---|
| ln Vitro |
2',3'-O-Isopropylideneadenosine demonstrates activity as an adenosine analog in cellular assays. Adenosine analogs mostly act as smooth muscle vasodilators and have been found to suppress cancer progression. The compound's in vitro activity is primarily studied in the context of nucleoside synthesis and as a precursor to bioactive nucleosides. Detailed IC50 values against specific targets have not been disclosed in publicly available literature.
|
| ln Vivo |
In vivo activity of 2',3'-O-Isopropylideneadenosine has not been extensively characterized as the compound is primarily a synthetic intermediate. Its derivatives, such as CI-IB-MECA (a selective A3 adenosine receptor agonist) and cordycepin, exhibit well-documented in vivo activities including vasodilation and anticancer effects. The protected compound itself is not typically used directly in vivo.
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| Enzyme Assay |
In vitro assays for adenosine analogs typically involve receptor binding studies using radiolabeled ligands or functional assays measuring cAMP accumulation. For nucleoside synthesis applications, standard organic chemistry methods are used. The compound is typically characterized by HPLC, NMR, and mass spectrometry to confirm identity and purity. Deprotection steps remove the isopropylidene group to yield the free nucleoside for biological studies.
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| Cell Assay |
Cells are not typically treated directly with 2',3'-O-Isopropylideneadenosine as it is a protected intermediate. The final deprotected nucleoside or derived compounds may be tested in cellular assays for adenosine receptor activity, vasodilation, or anticancer effects. Standard protocols for nucleoside analog studies in cell lines can be adapted.
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| Animal Protocol |
In vivo animal studies for 2',3'-O-Isopropylideneadenosine have not been reported. The compound is primarily used as a research tool and synthetic intermediate. Future studies in animal models of cancer or cardiovascular disease would be needed to evaluate the in vivo efficacy of its derivatives.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 2',3'-O-Isopropylideneadenosine have not been published. The compound has a molecular weight of 276.29 and formula C13H16N4O4. The isopropylidene protection may affect cellular permeability and stability. As a protected nucleoside, it is expected to be deprotected in vivo. In vivo PK parameters have not been characterized.
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| Toxicity/Toxicokinetics |
Toxicology data for 2',3'-O-Isopropylideneadenosine have not been published. The compound is for research use only and not approved for human therapeutic applications. No systematic toxicological evaluation has been performed. Standard safety precautions for handling chemical intermediates should be observed.
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| References | |
| Additional Infomation |
See also: 2',3'-O-isoproterenol (note moved to).
2',3'-O-Isopropylideneadenosine (CAS: 362-75-4, molecular formula C13H16N4O4, molecular weight 276.29) is an adenine nucleoside analog and synthetic intermediate. It is widely utilized in nucleoside synthesis for developing antiviral and anticancer drugs. It is not in clinical trials and has no regulatory approval. The compound is supplied as a research-grade intermediate for laboratory use only. |
| Molecular Formula |
C13H17N5O4
|
|---|---|
| Molecular Weight |
307.31
|
| Exact Mass |
307.128
|
| CAS # |
362-75-4
|
| Related CAS # |
2',3'-O-Isopropylideneadenosine-13C5
|
| PubChem CID |
2723654
|
| Appearance |
White to off-white solid powder
|
| Density |
1.8±0.1 g/cm3
|
| Boiling Point |
570.5±60.0 °C at 760 mmHg
|
| Melting Point |
221-222 °C(lit.)
|
| Flash Point |
298.8±32.9 °C
|
| Vapour Pressure |
0.0±1.7 mmHg at 25°C
|
| Index of Refraction |
1.797
|
| LogP |
1.15
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
22
|
| Complexity |
439
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=NC4=C(N=CN=C43)N)CO)C
|
| InChi Key |
LCCLUOXEZAHUNS-WOUKDFQISA-N
|
| InChi Code |
InChI=1S/C13H17N5O4/c1-13(2)21-8-6(3-19)20-12(9(8)22-13)18-5-17-7-10(14)15-4-16-11(7)18/h4-6,8-9,12,19H,3H2,1-2H3,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1
|
| Chemical Name |
[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
|
| 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 (~325.4 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (16.27 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 (50.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2540 mL | 16.2702 mL | 32.5404 mL | |
| 5 mM | 0.6508 mL | 3.2540 mL | 6.5081 mL | |
| 10 mM | 0.3254 mL | 1.6270 mL | 3.2540 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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