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| Targets |
As a thymidine analog, this compound targets the DNA replication machinery. It is incorporated into DNA during the S-phase of the cell cycle by cellular DNA polymerases. It acts as a replacement for the natural nucleoside, deoxythymidine. By being incorporated into DNA, it can be used to detect and visualize cell proliferation, as it substitutes for thymidine in newly synthesized DNA strands.
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| ln Vitro |
In vitro, this thymidine analog is used in cell labeling studies. When added to cell culture media, it is taken up by cells and incorporated into the DNA of dividing cells during replication. Its incorporation can be detected by various methods, such as using a labeled version of the compound (e.g., fluorescent or biotinylated). It does not typically have a direct cytotoxic effect but serves as a marker of DNA synthesis and cell proliferation.
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| ln Vivo |
In vivo, the compound is used to label proliferating cells in animal models. For example, it can be administered to mice to study cell turnover in specific tissues, such as the intestinal epithelium or the hematopoietic system. By subsequently analyzing tissue sections for the incorporated analog, researchers can visualize and quantify the number of cells that were in the DNA synthesis (S) phase during the labeling period.
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| Enzyme Assay |
For a cell-free assay, the compound can be used as a substrate in a DNA polymerase activity assay. The reaction mixture contains DNA polymerase, a DNA template with a complementary sequence, and a mixture of deoxynucleoside triphosphates (dNTPs), where the dTTP is replaced with this thymidine analog (likely as a triphosphate derivative). The incorporation of the analog into the growing DNA chain can be detected by gel electrophoresis or by using radioactive or fluorescently labeled forms of the compound.
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| Cell Assay |
In cellular assays, adherent or suspension cells are cultured in a 6- or 24-well plate. The compound is added to the culture medium at a defined concentration (e.g., 10 uM). Cells are incubated with the analog for a period ranging from 30 minutes to 24 hours, allowing for its incorporation into replicating DNA. After incubation, cells are fixed, permeabilized, and then stained with a detection reagent that specifically binds to the incorporated analog. The signal is then visualized and quantified by flow cytometry or fluorescence microscopy.
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| Animal Protocol |
In an animal study, the compound can be administered to mice via intraperitoneal (IP) injection at a specific dose (e.g., 50 mg/kg). At various time points after injection (e.g., 2, 12, 24 hours), the animals are euthanized, and tissues of interest (e.g., spleen, intestine, bone marrow) are harvested. These tissues are then processed for immunohistochemistry (IHC). Sections are stained to detect the incorporated analog, allowing for the visualization and quantification of proliferating cells in their native tissue environment.
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| ADME/Pharmacokinetics |
Specific ADME (Absorption, Distribution, Metabolism, and Excretion) data for this compound is not provided. However, as a thymidine analog, its pharmacokinetics are expected to involve cellular uptake via nucleoside transporters and rapid phosphorylation by thymidine kinase to its monophosphate form (TMP). The compound is soluble in DMSO at 250 mg/mL, allowing for the preparation of stock solutions for in vivo administration. It is recommended to store it at 4degC, protected from light.
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of Medication Use During Lactation Telbivudine has been discontinued in the US market. No studies have been conducted on breastfeeding women receiving treatment for hepatitis B. Alternative medications are recommended, especially for breastfeeding newborns or premature infants. As long as the infant receives hepatitis B immunoglobulin and hepatitis B vaccine at birth, there is no difference in infection rates between breastfed and formula-fed infants born to mothers with hepatitis B. Mothers with hepatitis B are encouraged to breastfeed after their infants have received these preventative measures. ◉ Impact on Breastfed Infants No published information found as of the revision date. ◉ Impact on Lactation and Breast Milk No published information found as of the revision date. Specific toxicology data for this compound is not presented in the summaries. As a research tool for labeling DNA synthesis, it is generally considered to have low toxicity and does not typically kill cells at standard labeling concentrations. Its primary use is as a marker, not as a cytotoxic agent. However, as with any analog incorporated into DNA, there may be long-term effects, though this is not a focus for its use as a research tool. It is not approved for clinical use. |
| References | |
| Additional Infomation |
1-(2-Deoxypentafuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinidone is a pyrimidine 2'-deoxyribonucleoside. L-thymidine has been reported in Penicillium commune, Fritillaria thunbergii, and other organisms with relevant data. See also: 1-(2'-Deoxy-β-threopentafuranosyl)thymidine (note moved to); thymidine (note moved to).
This compound is a specialized thymidine analog distinguished by its "beta-D-threo" sugar configuration. It is part of a class of compounds that are chemically similar to the natural nucleoside thymidine. Its primary application is as a research tool for studying DNA replication and cell proliferation. It can serve as an alternative to other well-known analogs like BrdU or EdU in labeling experiments, offering different properties, such as potentially less steric hindrance for detection. It is not a drug but a research chemical. |
| Molecular Formula |
C10H14N2O5
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|---|---|
| Molecular Weight |
242.23
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| Exact Mass |
242.09
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| CAS # |
16053-52-4
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| PubChem CID |
1134
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| Appearance |
White to off-white solid powder
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| Density |
1.452g/cm3
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| Index of Refraction |
1.584
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| LogP |
-1.2
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
17
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| Complexity |
381
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=CN(C(=O)NC1=O)[C@H]2C[C@H]([C@H](O2)CO)O
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| InChi Key |
IQFYYKKMVGJFEH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)
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| Chemical Name |
1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
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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) |
DMSO: 250 mg/mL (1032.08 mM)
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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 | 4.1283 mL | 20.6415 mL | 41.2831 mL | |
| 5 mM | 0.8257 mL | 4.1283 mL | 8.2566 mL | |
| 10 mM | 0.4128 mL | 2.0642 mL | 4.1283 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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