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| Other Sizes |
| Targets |
dUTP targets DNA polymerases, serving as a substrate for DNA synthesis. It can be incorporated into DNA in place of dTTP. dUTP is also a substrate for uracil-DNA glycosylase, an enzyme involved in DNA repair that removes uracil from DNA. The compound's role in DNA repair makes it a valuable tool for studying DNA damage and repair mechanisms.
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| ln Vitro |
dUTP demonstrates in vitro activity as a substrate for DNA polymerases in PCR, DNA labeling, and sequencing. It can be incorporated into DNA in place of dTTP. The compound is also used in assays to measure uracil-DNA glycosylase activity. Its activity is assessed by its ability to support DNA synthesis and repair reactions.
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| ln Vivo |
dUTP is involved in DNA synthesis and repair in vivo. It is a normal intermediate in nucleotide metabolism. dUTP is also a substrate for uracil-DNA glycosylase, which removes uracil from DNA to prevent mutagenesis. The compound's role in DNA repair makes it essential for maintaining genomic stability.
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| Enzyme Assay |
dUTP is used as a substrate in DNA polymerase assays and uracil-DNA glycosylase assays. DNA polymerase activity is measured by incorporating dUTP into DNA. Uracil-DNA glycosylase activity is measured by the removal of uracil from DNA containing dUTP. The assays typically use radiolabeled or fluorescently labeled substrates.
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| Cell Assay |
dUTP is used in cell-free in vitro assays such as PCR, DNA labeling, and DNA repair assays. It is added to reaction mixtures containing DNA polymerase or DNA repair enzymes. The compound's ability to support DNA synthesis or repair is assessed by measuring the reaction products.
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| Animal Protocol |
dUTP is not typically administered in animal experiments as a therapeutic agent. It is a naturally occurring nucleotide that is involved in DNA synthesis and repair. Its role in DNA repair makes it essential for maintaining genomic stability in all living organisms.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Organophosphate metabolism primarily occurs through oxidation, esterase hydrolysis, and reactions with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphate pesticides can produce moderately toxic products. Generally, thiophosphates themselves are not directly toxic and require oxidative metabolism to be converted into proximal toxins. Products produced by glutathione transferase reactions are generally less toxic. Paraoxygenase (PON1) is a key enzyme in organophosphate metabolism. PON1 can inactivate certain organophosphates through hydrolysis. PON1 hydrolyzes active metabolites in various organophosphate pesticides and nerve agents such as soman, sarin, and VX. The existence of PON1 polymorphism leads to differences in the enzyme level and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effects of organophosphate exposure. dUTP is a naturally occurring nucleotide that is synthesized intracellularly. Its concentration is tightly regulated within cells to prevent excessive incorporation of uracil into DNA. dUTP is involved in DNA synthesis and repair. The compound is used as a research reagent in molecular biology applications. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Deoxyuridine triphosphate (dUTP) can be misincorporated into DNA and cause DNA damage. The extent of DNA damage caused by dUTP depends on the levels of dUTPase pyrophosphatase and uracil-DNA glycosidase (UDG). DNA damage due to dUTP misincorporation is highly dependent on the level of dUTPase pyrophosphatase, which limits the accumulation of intracellular dUTP. (A4337) Furthermore, in some cell lines, inhibition of thymidylate synthase (TS) leads to loss of cell viability due to dUTP accumulation and subsequent misincorporation of uracil into DNA. (PMCID: PMC2364072) dUTP is a naturally occurring nucleotide and is not considered toxic at physiological concentrations. However, imbalances in dUTP levels can lead to increased uracil incorporation into DNA and genomic instability. The compound is intended for research use only. Standard laboratory safety precautions should be followed when handling this compound. |
| References | |
| Additional Infomation |
DUTP is a deoxyuridine phosphate with a triphosphate group at the 5' position. It is found in humans, Escherichia coli, mice, and Arabidopsis thaliana as a metabolite. It is a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate ester, and also a deoxyuridine phosphate. It is the conjugate acid of dUTP(3-). Deoxyuridine triphosphate is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain). It has also been reported to exist in Homo sapiens and cattle, with relevant data available. Deoxyuridine triphosphate is a uracil nucleotide composed of three phosphate groups esterified onto a deoxyribose glycosyl group. Deoxyuridine triphosphate is an intermediate in pyrimidine metabolism. It is a substrate of inosine triphosphate pyrophosphatase, deoxyuridine 5'-triphosphate nucleotide hydrolase (mitochondria), uridine cytidine kinase 1, nucleoside diphosphate kinase 3, nucleoside diphosphate kinase B, nucleoside diphosphate kinase 6, nucleoside diphosphate kinase (mitochondria), nucleoside diphosphate kinase homolog 5, nucleoside diphosphate kinase A, and nucleoside diphosphate kinase 7. Deoxyuridine triphosphate is a metabolite found or produced in Saccharomyces cerevisiae.
dUTP trisodium (2'-Deoxyuridine-5'-triphosphate trisodium salt) (CAS#: 102814-08-4) has the molecular formula C9H12N2O14P3·3Na and a molecular weight of 534.09. It is a nucleotide used in DNA synthesis, PCR, DNA labeling, and DNA repair studies. dUTP is a substrate for DNA polymerases and uracil-DNA glycosylase. It is for research use only. |
| Molecular Formula |
C9H12N2NA3O14P3
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|---|---|
| Molecular Weight |
534.09
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| Exact Mass |
511.937
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| CAS # |
102814-08-4
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| Related CAS # |
dUTP sodium;94736-09-1
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| PubChem CID |
65070
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| Appearance |
White to off-white solid powder
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| Density |
2.01g/cm3
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| LogP |
-5.5
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
28
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| Complexity |
808
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| Defined Atom Stereocenter Count |
3
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| SMILES |
C1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O
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| InChi Key |
AHCYMLUZIRLXAA-SHYZEUOFSA-N
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| InChi Code |
InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
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| Chemical Name |
[[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
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| Synonyms |
2'-Deoxyuridine-5'-triphosphate trisodium salt; dUTP trisodium
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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: Please store this product in a sealed and protected environment, 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)
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| Solubility (In Vitro) |
H2O : ~125 mg/mL (~234.0 mM)
DMSO : < 1 mg/mL |
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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 | 1.8723 mL | 9.3617 mL | 18.7234 mL | |
| 5 mM | 0.3745 mL | 1.8723 mL | 3.7447 mL | |
| 10 mM | 0.1872 mL | 0.9362 mL | 1.8723 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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