| Size | Price | |
|---|---|---|
| 50mg | ||
| Other Sizes |
| Targets |
As a purine nucleoside analog, this compound targets the DNA synthesis machinery, specifically DNA polymerases and other enzymes involved in nucleic acid metabolism. Its mechanism is hypothesized to involve incorporation into replicating DNA, leading to chain termination and inhibition of cell proliferation. The broad-spectrum antitumor activity of purine nucleoside analogs is attributed to their ability to act as antimetabolites.
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|---|---|
| ln Vitro |
In vitro, as a purine nucleoside analog, it exhibits broad-spectrum anticancer activity, targeting indolent lymphoid malignancies. The anti-cancer mechanism relies on inhibiting DNA synthesis and inducing apoptosis (programmed cell death). It is used for research purposes to study the mechanisms of action of nucleoside analogs in cancer cells.
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| ln Vivo |
The literature does not report specific in vivo studies for this exact compound. However, as a purine nucleoside analog, it is expected to have antitumor activity in animal models. It may be used in drug discovery to develop new anticancer or immunomodulatory agents. The benzoate esters act as protecting groups, and the chloro group can be substituted to create more active derivatives.
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| Enzyme Assay |
Cell-free assays for this compound would typically involve DNA polymerase inhibition assays. DNA polymerase and a DNA template are incubated with a mixture of deoxynucleotide triphosphates (dNTPs) and the analog (as a triphosphate derivative). The incorporation of the analog into the DNA strand is measured by scintillation or gel electrophoresis to assess its effect on DNA synthesis.
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| Cell Assay |
In cellular assays, cancer cell lines (e.g., chronic lymphocytic leukemia or lymphoma cells) are treated with serial dilutions of the compound for 48-72 hours. Cell viability is measured using an MTT or CellTiter-Glo assay. To confirm the mechanism of action, induction of apoptosis is assessed by flow cytometry (Annexin V/PI staining), and the effect on DNA synthesis can be measured by 3H-thymidine incorporation.
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| Animal Protocol |
As a nucleoside analog, in vivo efficacy could be studied in immunocompromised mice bearing xenografts of human lymphoma or leukemia cells. The compound would be formulated in a suitable vehicle (e.g., DMSO/PEG300/Tween-80/saline) and administered intraperitoneally (IP) daily. Tumor volume and survival are measured as endpoints. However, no specific protocol for this compound is found in the literature.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic (PK) data for this compound is not provided. It is a purine nucleoside analog with a molecular weight of 496.87. The presence of the benzoate groups would likely increase its lipophilicity (LogP: 5.11), potentially enhancing cellular permeability but also subjecting it to rapid hydrolysis by ubiquitous esterases in vivo, which would release the active nucleoside.
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| Toxicity/Toxicokinetics |
The literature does not contain toxicology data for this specific compound. As a purine nucleoside analog, known class effects include myelosuppression, immunosuppression, and gastrointestinal disturbances. However, as a research tool, it is handled with standard laboratory precautions. The compound itself is a synthetic intermediate, and detailed toxicological evaluation is not a primary focus.
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| References |
[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.
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| Additional Infomation |
This compound is a synthetic intermediate for clofarabine or other 2'-fluoro-arabinonucleosides. The benzoyl groups protect the 3' and 5'-hydroxyls during chemical synthesis. The 2'-fluoro and arabino configuration are essential for activity against certain targets. The chloro group at the 6-position of the purine is a leaving group that can be readily displaced by nucleophiles (e.g., amines) to create a variety of nucleoside analog libraries for drug discovery.
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| Molecular Formula |
C24H18CLFN4O5
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|---|---|
| Molecular Weight |
496.87
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| Exact Mass |
496.094
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| CAS # |
135473-15-3
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| PubChem CID |
54373568
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
665.6±65.0 °C at 760 mmHg
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| Flash Point |
356.4±34.3 °C
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| Vapour Pressure |
0.0±2.0 mmHg at 25°C
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| Index of Refraction |
1.682
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| LogP |
5.11
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
35
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| Complexity |
753
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| Defined Atom Stereocenter Count |
4
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| SMILES |
ClC1C2=C(N=CN=1)N(C=N2)[C@H]1[C@H]([C@@H]([C@@H](COC(C2C=CC=CC=2)=O)O1)OC(C1C=CC=CC=1)=O)F
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| InChi Key |
UUXIUBHNOYWBNO-ZRAXVTTISA-N
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| InChi Code |
InChI=1S/C24H18ClFN4O5/c25-20-18-21(28-12-27-20)30(13-29-18)22-17(26)19(35-24(32)15-9-5-2-6-10-15)16(34-22)11-33-23(31)14-7-3-1-4-8-14/h1-10,12-13,16-17,19,22H,11H2/t16-,17+,19-,22-/m1/s1
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| Chemical Name |
[(2R,3R,4S,5R)-3-benzoyloxy-5-(6-chloropurin-9-yl)-4-fluorooxolan-2-yl]methyl benzoate
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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) |
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 | 2.0126 mL | 10.0630 mL | 20.1260 mL | |
| 5 mM | 0.4025 mL | 2.0126 mL | 4.0252 mL | |
| 10 mM | 0.2013 mL | 1.0063 mL | 2.0126 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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