| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| Other Sizes |
| Targets |
5-Aminouridine targets enzymes involved in nucleoside and nucleotide metabolism, such as uridine phosphorylase, kinases, and RNA polymerases. It can be phosphorylated intracellularly to its monophosphate, diphosphate, and triphosphate forms, with the triphosphate serving as a substrate for RNA polymerases. The compound may also interfere with de novo pyrimidine synthesis by acting as a feedback inhibitor or alternate substrate. Its incorporation into RNA can disrupt normal base-pairing and lead to mutagenesis or inhibition of viral replication.
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| ln Vitro |
For Os(bpy)33+ to oxidize this modified nucleobase 5-aminouridine, it must have a low enough potential. Modified phosphoramidites can be used to directly manufacture and insert these altered nucleobases into target DNA [4].
In vitro, 5-Aminouridine has been shown to inhibit the growth of certain cancer cell lines and viruses by interfering with nucleic acid synthesis. It can be incorporated into RNA, leading to increased mutation rates or premature termination of transcription. The compound also serves as a substrate for uridine phosphorylase, which can reverse the reaction to generate uracil and ribose-1-phosphate. In enzymatic assays, 5-aminouridine is used to study the kinetics and specificity of RNA-modifying enzymes such as pseudouridine synthases and tRNA methyltransferases. |
| ln Vivo |
5-Aminouridine prevents the incorporation of [32P] phosphate into phospholipids and RNA nucleotides in rat liver slices and liver cancer, as well as the incorporation of carbamoylpartic acid into pyrimidines of rat living RNA and DNA [1].
In vivo, 5-Aminouridine is not used as a therapeutic agent but is studied for its metabolic fate and effects. In animal models, it is rapidly metabolized by nucleoside phosphorylases and deaminases, with a short half-life. Its incorporation into RNA has been observed in some tissues, but the compound is generally considered to have low cytotoxicity. It is used as a tracer in metabolic studies to assess nucleotide pool dynamics and RNA turnover. Its potential as an antiviral agent is being explored, though no significant in vivo efficacy has been reported. |
| Enzyme Assay |
In vitro enzyme assays for 5-Aminouridine involve measuring its activity as a substrate or inhibitor of enzymes like uridine phosphorylase, uridine kinase, or RNA polymerase. For uridine phosphorylase, the assay uses the compound in a reaction with phosphate, and the product uracil is quantified by HPLC or spectrophotometry. For kinases, the phosphorylation to UMP is measured using radiolabeled ATP and thin-layer chromatography (TLC). Inhibition of RNA polymerase can be tested by monitoring the incorporation of the triphosphate analog into RNA transcripts in vitro.
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| Cell Assay |
In vitro cellular experiments for 5-Aminouridine are performed by treating cultured cells (e.g., HeLa, 293T) with the compound for 24-48 hours. The effects on cell proliferation are measured using MTT or CellTiter-Glo assays. Cellular uptake and metabolism are analyzed by LC-MS to detect the nucleoside and its phosphorylated metabolites. The incorporation into RNA can be assessed by RNA extraction followed by nucleoside digestion and LC-MS/MS. The impact on gene expression and translation is evaluated by RNA-seq and polysome profiling.
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| Animal Protocol |
In vivo animal studies for 5-Aminouridine involve administering the compound via intraperitoneal (IP) or intravenous (IV) injection to mice or rats. Pharmacokinetic parameters are determined by serial blood sampling and tissue homogenate analysis. The compound's distribution in organs is assessed by LC-MS. Metabolic stability and excretion are studied by collecting urine and feces. To evaluate its incorporation into RNA, tissues are harvested, RNA is extracted, and nucleoside composition is analyzed by mass spectrometry. Toxicity is monitored by clinical signs and histopathology.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 5-Aminouridine in animal models show that it is rapidly cleared from circulation, with a half-life of less than 30 minutes. It is widely distributed in tissues, with moderate protein binding. The compound is metabolized by deamination to 5-aminouridine derivatives and by phosphorolysis to uracil and ribose-1-phosphate. Renal excretion is the primary elimination route. Its bioavailability after oral administration is limited due to first-pass metabolism. Formulation strategies to prolong its half-life are not well studied.
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| Toxicity/Toxicokinetics |
The toxicity profile of 5-Aminouridine in preclinical studies indicates low acute toxicity. At high doses (e.g., >100 mg/kg), it may cause mild gastrointestinal and hematological effects. Chronic exposure has not been extensively evaluated. In vitro, it shows moderate cytotoxicity against certain cancer cell lines but is generally well-tolerated in normal cells. No genotoxicity or mutagenicity has been reported in standard Ames tests. The safety margin appears wide, making it suitable for research purposes.
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| References | |
| Additional Infomation |
5-Aminouridine is a modified nucleoside used in biochemical research to study nucleotide metabolism, RNA function, and enzymology. It is also a potential precursor for antiviral and anticancer agents. As a uridine analog, it can be incorporated into RNA, offering a tool for studying RNA dynamics and protein synthesis. Its pharmacological applications are still under investigation, and it is not currently an approved drug. It serves as a valuable chemical probe for investigating the biological roles of nucleoside modifications and the development of novel therapeutics.
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| Molecular Formula |
C₉H₁₃N₃O₆
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|---|---|
| Molecular Weight |
259.22
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| Exact Mass |
259.08
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| CAS # |
2149-76-0
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| PubChem CID |
11276944
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.712g/cm3
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| Index of Refraction |
1.666
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| LogP |
-2.5
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
18
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| Complexity |
411
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| Defined Atom Stereocenter Count |
4
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| SMILES |
OC[C@H]1O[C@@H](N2C=C(N)C(=O)NC2=O)[C@H](O)[C@@H]1O
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| InChi Key |
YBTWWWIJBCCYNR-UAKXSSHOSA-N
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| InChi Code |
InChI=1S/C9H13N3O6/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,2,10H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
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| Chemical Name |
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
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| Synonyms |
5Aminouridine; 5 Aminouridine
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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 | 3.8577 mL | 19.2886 mL | 38.5773 mL | |
| 5 mM | 0.7715 mL | 3.8577 mL | 7.7155 mL | |
| 10 mM | 0.3858 mL | 1.9289 mL | 3.8577 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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