| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg | |||
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| Targets |
5-Hydroxy-2'-deoxyuridine targets DNA polymerases and repair enzymes. It is incorporated into DNA instead of thymidine, causing misincorporation and subsequent mutagenesis. The hydroxyl group at C5 can form reactive oxygen species (ROS) upon oxidation, leading to further DNA damage. The compound is a substrate for base excision repair (BER) enzymes, such as endonuclease III (NTHL1) and 8-oxoguanine DNA glycosylase (OGG1), which remove the damaged base. Its presence in DNA signals oxidative stress and can activate DNA damage response pathways.
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| ln Vitro |
In order to investigate the specificity of nucleotide incorporation with respect to 5-hydroxypyrimidine in template DNA, 18- and 45-membered oligodeoxyribonucleotides with internal 2'-deoxy- 5-hydroxyuridine (5-OHdU) were utilized. 2'-deoxy-5-hydroxyuridine (5-OHdU) was used to synthesize translesion in both oligonucleotides; however, it was seen one nucleotide ahead of and in the opposite position of the changed base in the template. Given 2'-deoxy-5-hydroxyuridine (5-OHdU) in the template, the specificity of nucleotide incorporation is contingent upon the context of the sequence. In a particular sequence context, the nucleotide integrated opposite 2'-deoxy-5-hydroxyuridine (5-OHdU) is dA. The main base opposite 2'-deoxy-5-hydroxyuridine (5-OHdU) in the second sequence context, however, is dC. Apart from 2'-deoxy-5-hydroxyuridine (5-OHdU), dC is the principal nucleotide incorporation in the same sequence context [1].
In vitro, 5-Hydroxy-2'-deoxyuridine is used as a standard in analytical assays to quantify DNA oxidation. It is also used in cell culture to induce oxidative stress and study DNA repair. At concentrations of 10-100 µM, it can be incorporated into the DNA of replicating cells, leading to cell cycle arrest and apoptosis. The compound is more potent than 5-bromo-2'-deoxyuridine (BrdU) in inducing DNA damage in certain cell lines. It is also used as a substrate to assess the activity of thymidine phosphorylase and other nucleoside-metabolizing enzymes. |
| ln Vivo |
In vivo, 5-Hydroxy-2'-deoxyuridine is not used therapeutically but is measured as a biomarker of oxidative DNA damage in urine and tissues. Elevated levels are found in patients with cancer, inflammatory diseases, or after exposure to ionizing radiation. In animal studies, administration of the compound (e.g., IP injection) has been used to model oxidative DNA damage and to study the efficacy of antioxidant treatments. It is rapidly excreted in urine, with a short half-life. Its role as a radiation sensitizer is under investigation but remains experimental.
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| Enzyme Assay |
In vitro enzyme assays for 5-Hydroxy-2'-deoxyuridine focus on its interaction with DNA polymerases and repair enzymes. For DNA polymerase, the incorporation efficiency of the nucleoside triphosphate (5-OH-dUTP) is measured using a primer extension assay with a fluorescence or radiolabeled readout. For BER enzymes, a glycosylase activity assay uses a 5-OH-dU-containing duplex oligonucleotide as a substrate; the abasic site generated is detected by AP endonuclease cleavage or using a fluorescent probe. The assay conditions (pH, salt, temperature) are optimized for each enzyme.
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| Cell Assay |
In vitro cellular experiments for 5-Hydroxy-2'-deoxyuridine involve treating cultured cells (e.g., fibroblasts, HeLa) with the compound (1-100 µM) for 24-72 hours. DNA damage is assessed by comet assay or by measuring γ-H2AX foci via immunofluorescence. Cell viability is determined by MTT. The compound's incorporation into DNA is verified by LC-MS/MS after DNA digestion. The effect on cell cycle progression and apoptosis is measured by flow cytometry. Repair kinetics are evaluated by time-course studies after removing the compound.
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| Animal Protocol |
In vivo animal studies for 5-Hydroxy-2'-deoxyuridine are typically not performed with the compound itself, but its levels are measured in biological samples from oxidative stress models (e.g., toxin-treated mice, radiation-exposed rats). The compound is extracted from urine or tissues and analyzed by LC-MS/MS. Its use as a tracer in pharmacokinetic studies is limited. The compound's ability to enhance radiation sensitivity has been assessed in mouse tumor models, but these are not standard.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 5-Hydroxy-2'-deoxyuridine are characterized by rapid absorption and elimination. It is quickly metabolized by thymidine phosphorylase to uracil derivatives and excreted renally. In humans, its half-life is about 30 minutes to 1 hour. The compound is not significantly protein-bound. Its concentration in tissues reflects local oxidative stress and DNA turnover. Formulation for therapeutic use has not been developed due to its toxicity at high doses and rapid clearance.
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| Toxicity/Toxicokinetics |
The toxicity profile of 5-Hydroxy-2'-deoxyuridine includes mutagenicity and cytotoxicity due to its incorporation into DNA. In vitro, it induces DNA strand breaks and apoptosis at millimolar concentrations. In vivo, high doses (e.g., >100 mg/kg) can cause myelosuppression and gastrointestinal toxicity in rodents, reflecting its effect on rapidly dividing cells. It is not approved for human use, and its safety margin is narrow. It is classified as a research chemical with potential genotoxic effects, requiring careful handling.
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| References | |
| Additional Infomation |
5-Hydroxy-2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside.
5-Hydroxy-2'-deoxyuridine is a modified nucleoside used as a biomarker for oxidative DNA damage and as a research tool in DNA repair and mutagenesis studies. It is a product of reactive oxygen species attack on thymidine, and its elevated levels are associated with various diseases. The compound is used to study the mechanisms of DNA oxidation, repair pathways, and the consequences of nucleoside modifications. It is also investigated as a potential radiosensitizer, but its clinical development is hindered by toxicity. It remains a valuable reagent in biochemical and molecular biology laboratories. |
| Molecular Formula |
C₉H₁₂N₂O₆
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| Molecular Weight |
244.20
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| Exact Mass |
244.07
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| CAS # |
5168-36-5
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| PubChem CID |
96622
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.698g/cm3
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| Index of Refraction |
1.654
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| LogP |
-1.7
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
17
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| Complexity |
382
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| Defined Atom Stereocenter Count |
3
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| SMILES |
C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)O)CO)O
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| InChi Key |
UIJSURSVLVISBO-UBKIQSJTSA-N
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| InChi Code |
InChI=1S/C9H12N2O6/c12-3-6-4(13)1-7(17-6)11-2-5(14)8(15)10-9(11)16/h2,4,6-7,12-14H,1,3H2,(H,10,15,16)/t4-,6+,7+/m0/s1
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| Chemical Name |
5-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
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| Synonyms |
5Hydroxy2'deoxyuridine; 5 Hydroxy 2' deoxyuridine
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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) |
DMSO : ~33.33 mg/mL (~136.49 mM)
H2O : ~10 mg/mL (~40.95 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2 mg/mL (8.19 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2 mg/mL (8.19 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: 2 mg/mL (8.19 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. Solubility in Formulation 4: 10 mg/mL (40.95 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0950 mL | 20.4750 mL | 40.9500 mL | |
| 5 mM | 0.8190 mL | 4.0950 mL | 8.1900 mL | |
| 10 mM | 0.4095 mL | 2.0475 mL | 4.0950 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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