| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
| Targets |
2',3'-Dideoxy-5-iodouridine targets viral reverse transcriptase and cellular DNA polymerases. As a nucleoside analog, it is phosphorylated intracellularly to the active triphosphate form, which competes with natural nucleotides for incorporation into DNA or viral cDNA. The 2',3'-dideoxy structure lacks the 3'-hydroxyl group, causing chain termination upon incorporation, which inhibits viral replication. The compound has been studied for activity against HIV and other retroviruses. It may also inhibit cellular DNA polymerases, contributing to its anticancer activity. The iodine substituent at the 5-position may enhance antiviral activity and facilitate radiolabeling.
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| ln Vitro |
In vitro, 2',3'-dideoxy-5-iodouridine exhibits antiviral activity against HIV-1 and other retroviruses through inhibition of reverse transcriptase. The compound is phosphorylated to the active triphosphate by cellular kinases, which then competes with dTTP for incorporation into viral DNA. Once incorporated, the lack of a 3'-hydroxyl group terminates DNA chain elongation. The compound also shows activity against certain cancer cell lines through inhibition of DNA synthesis. However, its activity is generally lower than that of other nucleoside analogs such as AZT. The iodine substituent may enhance lipophilicity and cellular uptake. IC₅₀ values for antiviral activity are typically in the micromolar range.
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| ln Vivo |
In vivo, 2',3'-dideoxy-5-iodouridine has been studied for antiviral and anticancer activity, but its clinical development has been limited by toxicity and pharmacokinetic issues. The compound is rapidly metabolized and cleared, with limited oral bioavailability. In animal models, it has shown some efficacy against retroviral infections, but the therapeutic index is narrow. The compound is not approved for human use as an antiviral or anticancer agent. Its primary application remains as a research reagent for studying nucleoside metabolism and as a precursor for radiolabeled compounds for PET or SPECT imaging applications.
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| Enzyme Assay |
In vitro antiviral assays for 2',3'-dideoxy-5-iodouridine typically involve HIV-1-infected MT-4 or CEM cells. Cells are cultured in 96-well plates and treated with varying concentrations of the compound (typically 0.01-100 µM) for 5-7 days. Viral replication is measured by p24 antigen production or by syncytium formation. Cytotoxicity is assessed using MTT assays to determine the selectivity index. For kinase assays, the compound is incubated with cellular extracts and ATP, and the phosphorylated product is analyzed by HPLC or mass spectrometry. For DNA polymerase inhibition, purified enzymes are incubated with template/primer and radiolabeled dNTPs.
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| Cell Assay |
In vitro cell culture experiments with 2',3'-dideoxy-5-iodouridine typically involve HIV-infected cells or cancer cell lines. Cells are cultured in RPMI medium supplemented with 10% FBS. The compound is dissolved in DMSO and diluted in culture medium to achieve desired concentrations (typically 0.1-100 µM). Cells are treated for 3-7 days, and cell viability is assessed using MTT or CellTiter-Glo assays. For antiviral studies, p24 antigen production is measured by ELISA. For anticancer studies, cell proliferation is assessed by BrdU incorporation or colony formation assays. Apoptosis is measured using Annexin V/PI staining.
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| Animal Protocol |
In vivo animal studies with 2',3'-dideoxy-5-iodouridine are limited, as the compound is primarily a research reagent. If conducted, typical protocols for antiviral studies involve HIV-infected SCID-hu mice or other retroviral models. Animals are treated orally or intraperitoneally with the compound at doses ranging from 10-100 mg/kg daily. Viral load and CD4+ T cell counts are monitored. For pharmacokinetic studies, blood samples are collected at various time points and analyzed by LC-MS/MS. Toxicology studies include histopathological examination of major organs. However, the compound is not used in clinical trials or approved for therapeutic use.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2',3'-dideoxy-5-iodouridine have been studied in animal models. Following oral administration, the compound has limited bioavailability due to first-pass metabolism and poor intestinal absorption. The compound is rapidly metabolized by deamination and other pathways. The elimination half-life is short (typically 1-2 hours). The compound is distributed to various tissues, but the presence of the iodine substituent may affect tissue distribution. The compound is primarily excreted in urine as metabolites. Formal pharmacokinetic studies are limited as the compound is not a drug candidate. For drug candidates derived from this nucleoside, pharmacokinetic properties are determined as part of drug development.
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| Toxicity/Toxicokinetics |
2',3'-Dideoxy-5-iodouridine may be harmful if swallowed, inhaled, or in contact with skin. The compound contains iodine, which may present additional hazards. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound should be stored in a cool, dry place away from light and moisture. No acute toxicity, mutagenicity, or carcinogenicity data are available. The compound is not intended for drug, household, or other uses. In case of exposure, rinse with water and seek medical attention.
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| References |
[1]. Dinesh Rai, et al. Inhibition of Mycobacterium tuberculosis, Mycobacterium bovis, and Mycobacterium avium by novel dideoxy nucleosides. J Med Chem. 2007 Sep 20;50(19):4766-74.
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| Additional Infomation |
Antiviral; structurally derived from first source
2',3'-Dideoxy-5-iodouridine is a nucleoside analog used as a research reagent for studying nucleoside metabolism and as a precursor for radiolabeled compounds for PET or SPECT imaging applications. It has been studied for antiviral activity against HIV and other retroviruses, as well as anticancer activity. The compound is also known as 5-iodo-2',3'-dideoxyuridine and 5-I-d4U. It has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action involves inhibition of viral reverse transcriptase and DNA chain termination following phosphorylation to the active triphosphate. |
| Molecular Formula |
C9H11IN2O4
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|---|---|
| Molecular Weight |
338.10
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| Exact Mass |
337.976
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| CAS # |
105784-83-6
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| PubChem CID |
451862
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| Appearance |
White to off-white solid powder
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| Density |
2.02g/cm3
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| Melting Point |
176ºC (dec.)(lit.)
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| Index of Refraction |
1.682
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| LogP |
-1.4
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
16
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| Complexity |
357
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| Defined Atom Stereocenter Count |
2
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| SMILES |
IC1C(N([H])C(N(C=1[H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])O[H])O1)=O)=O
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| InChi Key |
OBGFSDPYSQAECJ-CAHLUQPWSA-N
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| InChi Code |
InChI=1S/C9H11IN2O4/c10-6-3-12(9(15)11-8(6)14)7-2-1-5(4-13)16-7/h3,5,7,13H,1-2,4H2,(H,11,14,15)/t5-,7+/m0/s1
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| Chemical Name |
1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-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: 100 mg/mL (295.77 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 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: ≥ 2.5 mg/mL (7.39 mM) (saturation unknown) 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. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 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: ≥ 2.5 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9577 mL | 14.7885 mL | 29.5770 mL | |
| 5 mM | 0.5915 mL | 2.9577 mL | 5.9154 mL | |
| 10 mM | 0.2958 mL | 1.4789 mL | 2.9577 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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