| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
The primary molecular target of 1-(β-D-Xylofuranosyl)-5-fluorouracil is thymidylate synthase (TS), a key enzyme in the nucleotide synthesis pathway. Once inside the cell, the compound is phosphorylated by cellular kinases to form active triphosphate metabolites . The active metabolite competitively inhibits thymidylate synthase by competing with deoxyuridine monophosphate for binding at the enzyme's active site, leading to depletion of thymidine triphosphate (dTTP) levels and subsequent impairment of DNA replication and repair . Additionally, the fluorinated analog can be misincorporated into RNA and DNA, causing faulty transcription and chain termination, ultimately inducing apoptosis in rapidly dividing cancer cells .
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|---|---|
| ln Vitro |
In vitro studies have demonstrated that 1-(β-D-Xylofuranosyl)-5-fluorouracil exhibits significant antitumor activity across various cancer cell lines . The compound shows broad-spectrum cytotoxic effects against colorectal cancer, breast cancer, and pancreatic cancer cell lines, with studies indicating that it may outperform traditional 5-FU in certain assays due to improved cellular uptake and retention . Notably, the compound has demonstrated effectiveness against resistant cell lines, suggesting a potential advantage over conventional chemotherapeutic agents . The anticancer mechanism relies on inhibition of DNA synthesis and induction of apoptosis, with the IC50 values varying depending on the specific cell line tested .
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| ln Vivo |
In vivo studies have confirmed the antitumor efficacy of 1-(β-D-Xylofuranosyl)-5-fluorouracil in animal models. Preclinical trials have shown promising results in inhibiting the proliferation of various tumor types, including colorectal cancers, breast cancers, and pancreatic cancers . The compound's enhanced therapeutic profile is attributed to its improved pharmacokinetic properties compared to standard 5-FU, including better cellular uptake and retention . Studies have also explored its potential in combination therapies, with preliminary evidence suggesting synergistic effects when used with other antineoplastic agents . According to TargetMol's product specifications, the compound can be formulated for in vivo administration using co-solvent systems such as DMSO, PEG300, Tween 80, and saline .
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| Enzyme Assay |
For assessing the enzyme inhibition activity of 1-(β-D-Xylofuranosyl)-5-fluorouracil, a standard thymidylate synthase inhibition assay can be performed. Purified thymidylate synthase enzyme is incubated with varying concentrations of the test compound in reaction buffer containing 50 mM Tris-HCl (pH 7.5), 15 mM MgCl₂, and 1 mM EDTA. The reaction is initiated by adding deoxyuridine monophosphate (dUMP) and 5,10-methylenetetrahydrofolate. After incubation at 37°C for 15-30 minutes, the reaction is terminated, and product formation is quantified spectrophotometrically at 340 nm or by HPLC . The compound's active metabolites inhibit TS by competing with dUMP for binding, and the radiolabeled precursor incorporation assay using tritiated deoxyuridine can be employed to measure the extent of TS inhibition .
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| Cell Assay |
Cellular assays for evaluating the cytotoxic effects of 1-(β-D-Xylofuranosyl)-5-fluorouracil are typically performed using cancer cell lines such as colorectal (e.g., HCT116, HT-29), breast (e.g., MCF-7), or pancreatic cancer cells . Cells are seeded in 96-well plates at appropriate densities (5 × 10³ cells/well) and cultured overnight. The test compound is added at varying concentrations (typically 0.1-200 μM) and incubated for 48-72 hours at 37°C in 5% CO₂ . Cell viability is assessed using MTT or CCK-8 assays, with absorbance measured at 450-570 nm to calculate the half-maximal inhibitory concentration (IC50) from dose-response curves . Apoptosis can be evaluated by flow cytometry using Annexin V/PI staining or TUNEL assay, while DNA synthesis inhibition is confirmed via tritiated thymidine incorporation studies .
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| Animal Protocol |
For in vivo evaluation of 1-(β-D-Xylofuranosyl)-5-fluorouracil, murine tumor xenograft models are commonly employed . Immunodeficient mice (e.g., nude mice) are subcutaneously injected with 5 × 10⁶ cancer cells (e.g., colorectal or pancreatic cancer cells) to establish tumors. When tumors reach approximately 100-150 mm³, animals are randomized into treatment groups (n=5-8). The compound is formulated using a co-solvent system such as 5% DMSO + 30% PEG300 + 5% Tween 80 + 60% saline, and administered via intraperitoneal or intravenous injection at doses determined from preliminary dose-finding studies . Tumor volumes are measured every 2-3 days using calipers, and body weight is monitored as an indicator of toxicity. At study termination, tumors are excised, weighed, and processed for histopathological examination including TUNEL staining for apoptosis detection .
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| ADME/Pharmacokinetics |
Specific pharmacokinetic parameters for 1-(β-D-Xylofuranosyl)-5-fluorouracil remain limited in publicly available literature. However, the compound is characterized by its improved pharmacokinetic profile compared to parent 5-fluorouracil, attributed to the xylose sugar modification which enhances cellular uptake and bioavailability . For research applications, storage recommendations include powder stability at -20°C for up to 3 years, and solutions at -80°C for up to 1 year . For in vivo formulations, a typical co-solvent system uses 5% DMSO, 30% PEG300, 5% Tween 80, and 60% saline to achieve appropriate solubility for animal administration . The compound is soluble in water and organic solvents including DMSO .
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| Toxicity/Toxicokinetics |
9427 mouse LD50 intravenous 250 mg/kg GASTROINTESTINAL: HYPERMOTILITY, DIARRHEA Proceedings of the Society for Experimental Biology and Medicine., 97(470), 1958 [PMID:13518307]
9427 mouse LD50 intraperitoneal 160 mg/kg GASTROINTESTINAL: HYPERMOTILITY, DIARRHEA; GASTROINTESTINAL: OTHER CHANGES Cancer Research., 39(2406), 1979 [PMID:156065] 9427 rat LD50 intraperitoneal 400 mg/kg Advances in Teratology., 3(181), 1968 9427 mouse LD50 subcutaneous 384 mg/kg GASTROINTESTINAL: HYPERMOTILITY, DIARRHEA Proceedings of the Society for Experimental Biology and Medicine., 97(470), 1958 [PMID:13518307] According to product specifications, 1-(β-D-Xylofuranosyl)-5-fluorouracil is classified for research use only and is not approved for human therapeutic or diagnostic applications . As a fluorouracil derivative, the compound carries potential for similar toxicity profiles as 5-FU, including myelosuppression, gastrointestinal toxicity (diarrhea, stomatitis, nausea), and hepatotoxicity, though the xylose sugar modification is intended to potentially reduce side effects associated with conventional 5-fluorouracil . In preclinical studies, side effects were reported as manageable, with no significant body weight loss observed in treated animals compared to controls . Standard safety precautions for laboratory handling include working in a well-ventilated area, wearing appropriate personal protective equipment (gloves, lab coat, safety goggles), and avoiding inhalation, ingestion, or skin contact . |
| References |
| Molecular Formula |
C9H11FN2O6
|
|---|---|
| Molecular Weight |
262.19
|
| Exact Mass |
262.0601142
|
| PubChem CID |
9427
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| Appearance |
Typically exists as solid at room temperature
|
| LogP |
-1.7
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| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
18
|
| Complexity |
414
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)F
|
| InChi Key |
FHIDNBAQOFJWCA-UAKXSSHOSA-N
|
| InChi Code |
InChI=1S/C9H11FN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
|
| Chemical Name |
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione
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| Synonyms |
5-Fluorouridine; 316-46-1; 5-Fur; 5-Fluoro-uridine; ...; 1-(b-D-Xylofuranosyl)-5-fluorouracil;
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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 | 3.8140 mL | 19.0701 mL | 38.1403 mL | |
| 5 mM | 0.7628 mL | 3.8140 mL | 7.6281 mL | |
| 10 mM | 0.3814 mL | 1.9070 mL | 3.8140 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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