![5'-O-[Bis(4-methoxyphenyl)phenylmethyl]-adenosine (5'-O-(4,4'-DIMETHOXYTRITYL)ADENOSINE)](/upload/1124/V75590.png)
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| Targets |
As a nucleoside analog, this compound can target the DNA synthesis machinery by being incorporated into replicating DNA. However, its primary use is not as a drug but as a chemical intermediate. It acts as a synthetic building block where the DMT group serves as a temporary protective group, preventing unwanted reactions at the 5'-hydroxyl during the stepwise addition of nucleotides in automated synthesizers.
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| ln Vitro |
In vitro, as a purine nucleoside analog, it can exhibit broad-spectrum anti-tumor activity by inhibiting DNA synthesis and inducing apoptosis. The compound is a chemical tool, and its activity is not for therapeutic use. Its primary in vitro function is as a reference standard or a starting material for synthesizing more complex biologically active molecules like antisense oligonucleotides.
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| ln Vivo |
In vivo, as a building block for oligonucleotide synthesis, this compound is not administered directly to animals for therapeutic effect. Instead, the DNA or RNA sequences created using this building block can be used in animal models for research purposes, such as gene silencing or targeted degradation studies. The compound itself has no direct in vivo activity.
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| Enzyme Assay |
Cell-free assays are not typically performed for this compound as a drug. Instead, its chemical purity and identity are confirmed by techniques such as HPLC, Mass Spectrometry, and NMR spectroscopy. If used in an enzymatic assay, it would be as a substrate for nucleoside kinases to study phosphorylation, but this is not a standard protocol for this protected building block.
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| Cell Assay |
As a chemical intermediate, this compound is not used in cell-based assays for biological activity. Instead, it is utilized in organic synthesis reactions on the benchtop. A typical protocol involves dissolving the compound in an anhydrous solvent (e.g., DCM or DMF) and reacting it with a nucleoside phosphoramidite in the presence of an activator to form a dinucleotide, which is the basis of solid-phase oligonucleotide synthesis.
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| Animal Protocol |
Animal studies are not performed with this compound as an investigational drug. However, the final oligonucleotides synthesized using this building block can be used in in vivo research. For example, an antisense oligonucleotide (ASO) synthesized with this building block can be formulated and administered to mice (e.g., via subcutaneous or intravenous injection) to study target gene knockdown in disease models.
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| ADME/Pharmacokinetics |
This compound is a chemical building block, not a drug, so its ADME is not characterized. It is stable and non-reactive when stored as a powder at -20degC, protected from light. It has a molecular weight of 569.61 and is soluble in solvents like DMSO (1.7556 mM solution is a typical stock solution). Its high LogP (3.634) suggests it is lipophilic.
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| Toxicity/Toxicokinetics |
The literature does not contain toxicological data for this compound as it is a synthetic intermediate. In standard chemical synthesis, appropriate lab safety measures (gloves, goggles, lab coat) should be taken when handling. As a solid, it is generally considered to be of low acute toxicity, but it is not intended for human consumption or as a therapeutic agent.
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| References |
[1]. Man S, et al. Potential and promising anticancer drugs from adenosine and its analogs. Drug Discov Today. 2021 Jun;26(6):1490-1500.
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| Additional Infomation |
This compound is not a drug but a crucial tool in molecular biology. The 5'-DMT (4,4'-Dimethoxytrityl) group is the most widely used protecting group for the 5'-hydroxyl in solid-phase DNA and RNA synthesis. Its rapid and quantitative deprotection under mild acidic conditions (e.g., dichloroacetic acid) is the key to the stepwise addition of nucleotides. It is an essential reagent for research in genetics and biotechnology, enabling the custom synthesis of primers, probes, and genes.
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| Molecular Formula |
C31H31N5O6
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| Molecular Weight |
569.61
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| Exact Mass |
569.227
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| CAS # |
81352-25-2
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| PubChem CID |
10951928
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| Appearance |
White to off-white solid powder
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| LogP |
3.634
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
42
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| Complexity |
826
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C(C1C=CC=CC=1)(C1C=CC(OC)=CC=1)(C1C=CC(OC)=CC=1)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC3C(=NC=NC2=3)N)O1
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| InChi Key |
KOQFCLKBHJBRTB-BQOYKFDPSA-N
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| InChi Code |
InChI=1S/C31H31N5O6/c1-39-22-12-8-20(9-13-22)31(19-6-4-3-5-7-19,21-10-14-23(40-2)15-11-21)41-16-24-26(37)27(38)30(42-24)36-18-35-25-28(32)33-17-34-29(25)36/h3-15,17-18,24,26-27,30,37-38H,16H2,1-2H3,(H2,32,33,34)/t24-,26-,27-,30-/m1/s1
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| Chemical Name |
(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
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
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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 | 1.7556 mL | 8.7779 mL | 17.5559 mL | |
| 5 mM | 0.3511 mL | 1.7556 mL | 3.5112 mL | |
| 10 mM | 0.1756 mL | 0.8778 mL | 1.7556 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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