| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
| Targets |
This compound is a purine/pyrimidine nucleoside analog. As a nucleoside analog, it has the potential to be recognized by cellular nucleoside kinases and incorporated into DNA or RNA, thereby interfering with nucleic acid synthesis. It is a research tool for studying nucleic acid metabolism.
|
|---|---|
| ln Vitro |
In vitro, 4',5'-Didehydro-5'-deoxyuridine is described as a purine nucleoside analog with broad-spectrum anticancer activity targeting indolent lymphoid malignancies. The presence of the double bond and the missing 5' hydroxyl group would make it a potential chain terminator if it can be phosphorylated. It can interfere with the function of enzymes involved in DNA/RNA synthesis.
|
| ln Vivo |
Specific in vivo activity data is not provided. As a nucleoside analog, its potential in vivo application would be as an anticancer agent. The activity is hypothesized based on its structural similarity to other active nucleoside analogs. It would need to be converted to its mono-, di-, and triphosphate forms inside cells to exert its effect.
|
| Enzyme Assay |
The compound is not used in a standard receptor binding assay. Its ability to be converted to an active triphosphate can be tested in a biochemical assay using purified enzymes. For instance, recombinant thymidine kinase (TK) or other nucleoside kinases can be incubated with 4',5'-Didehydro-5'-deoxyuridine and ATP. The reaction mixture is then analyzed by HPLC to detect the formation of the monophosphorylated product, which is the first and often rate-limiting step for activation.
|
| Cell Assay |
Cell-based assays to evaluate its anti-cancer potential are performed on sensitive cell lines. A standard protocol involves treating various cancer cell lines (e.g., B-cell leukemia lines) with a range of concentrations of 4',5'-Didehydro-5'-deoxyuridine for 72 hours. Cell proliferation and viability are then measured using an MTS or WST-1 assay. A cytotoxicity curve is generated to determine the IC₅0. Induction of apoptosis can be confirmed by flow cytometry.
|
| Animal Protocol |
Specific in vivo protocols are not provided. A typical study for a new nucleoside analog would use a mouse xenograft model. For example, a human lymphoma cell line is implanted subcutaneously into NOD/SCID mice. 4',5'-Didehydro-5'-deoxyuridine is administered intraperitoneally daily. Tumor size and body weight are measured three times a week. At the end of the study, tumors are harvested for analysis of DNA synthesis inhibition or apoptosis markers.
|
| ADME/Pharmacokinetics |
No specific PK data is available for this compound. The presence of a 4',5'-double bond is likely to make it extremely resistant to degradation by cellular nucleotidases and glycosylases, potentially increasing its half-life compared to natural nucleosides. Its lipophilicity would be different, affecting its cellular uptake.
|
| Toxicity/Toxicokinetics |
No specific toxicity data is available. As an analog that inhibits DNA synthesis, it is likely to have a toxicity profile similar to other anti-metabolites, causing bone marrow suppression and gastrointestinal effects. Its selectivity for cancer cells would need to be determined.
|
| 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.
|
| Additional Infomation |
This compound is a 5'-deoxy and unsaturated version of uridine. The term "purine nucleoside analog" in the provided text (29-L10, 29-L21) is likely a misclassification, as it is a pyrimidine (uracil) analog. It represents a class of "locked" or "unsaturated" nucleosides. Such modifications are common in medicinal chemistry to improve metabolic stability and target specificity. It remains a research chemical with no approved clinical use.
|
| Molecular Formula |
C9H10N2O5
|
|---|---|
| Molecular Weight |
226.19
|
| Exact Mass |
226.059
|
| CAS # |
14365-63-0
|
| PubChem CID |
13146158
|
| Appearance |
White to off-white solid powder
|
| LogP |
-1.7
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
16
|
| Complexity |
391
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
O1C(=C([H])[H])C([H])(C([H])(C1([H])N1C([H])=C([H])C(N([H])C1=O)=O)O[H])O[H]
|
| InChi Key |
WMIBCMZGMYGWHB-BWZBUEFSSA-N
|
| InChi Code |
InChI=1S/C9H10N2O5/c1-4-6(13)7(14)8(16-4)11-3-2-5(12)10-9(11)15/h2-3,6-8,13-14H,1H2,(H,10,12,15)/t6-,7-,8-/m1/s1
|
| Chemical Name |
1-[(2R,3R,4S)-3,4-dihydroxy-5-methylideneoxolan-2-yl]pyrimidine-2,4-dione
|
| 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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 (442.11 mM)
|
|---|---|
| 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 | 4.4211 mL | 22.1053 mL | 44.2106 mL | |
| 5 mM | 0.8842 mL | 4.4211 mL | 8.8421 mL | |
| 10 mM | 0.4421 mL | 2.2105 mL | 4.4211 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
