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| Targets |
DNA/RNA (incorporates into nucleic acids); Reactive Oxygen Species (ROS) generation. 2-Selenouracil targets the cellular genome and transcriptome as a nucleobase analog; it can be incorporated into RNA (or DNA in replicating cells) by cellular polymerases, disrupting nucleic acid structure and function. Upon photoactivation (UVA/blue light), it acts as a Type II photosensitizer, transferring energy to molecular oxygen to generate singlet oxygen (¹O2). It can also undergo photochemical reactions with adjacent biomolecules (DNA, proteins), leading to crosslinking. It possesses antioxidant properties due to the redox-active selenium atom, scavenging peroxynitrite (ONOO-) and other radicals. It has dual activity: antioxidant in the dark, phototoxic in the light.
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| ln Vitro |
In vitro, 2-Selenouracil (1-100 uM) is not toxic in the dark (no dark cytotoxicity). Upon irradiation with UVA light (e.g., 365 nm, 1-5 J/cm2), it generates ROS (detected by DCFH-DA or SOSG) and induces cell death in cancer cells (e.g., HeLa, MCF-7). It causes DNA damage, as measured by the comet assay or gamma-H2AX foci. It also has antioxidant activity in the dark, scavenging DPPH radicals (IC₅0 ~10-50 uM) and superoxide (O2•-). It can be incorporated into RNA in cell culture, interfering with RNA processing and translation. It is a bifunctional molecule: antioxidant (dark) and photosensitizer (light).
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| ln Vivo |
In vivo, 2-Selenouracil is a promising photosensitizer for photodynamic therapy. In mouse xenograft models (e.g., melanoma), intratumoral or topical application of 2-Selenouracil (e.g., 0.1-1 mM) followed by UVA light exposure (e.g., 365 nm, 100-200 J/cm2) results in significant tumor growth delay or regression. It induces photodynamic damage, apoptosis, and necrosis. It has low systemic toxicity in the dark. It is excreted rapidly. Because it is a nucleobase analog, it may have teratogenic potential (like other selenouracils). However, its in vivo efficacy in PDT is being explored. It shows potential for treating skin cancers and superficial lesions. Studies on deep-seated tumors are limited due to poor penetration of UVA light.
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| Enzyme Assay |
Singlet oxygen generation assay (cell-free): Dissolve 2-Selenouracil in PBS (1-100 uM). Add a singlet oxygen sensor (e.g., SOSG, 1 uM). Irradiate with a UVA lamp (300-400 nm) or a specific wavelength LED (e.g., 365 nm). Measure SOSG fluorescence increase at ex/em 504/525 nm. For DPPH radical scavenging (antioxidant assay in the dark), mix 2-Selenouracil (0-500 uM) with DPPH (0.1 mM) in methanol. Incubate for 30 min in the dark. Measure at 517 nm. This quantifies the dark antioxidant capacity. For DNA damage assays in cell-free systems, incubate plasmid DNA with 2-Selenouracil (1-100 uM) and UVA light. Analyze DNA nicking by agarose gel electrophoresis.
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| Cell Assay |
Photocytotoxicity assay: Seed cancer cells (e.g., HeLa, A431) in 96-well plates. Treat with 2-Selenouracil (0-200 uM) for 4-24 hours. Wash cells (optional, to remove extracellular compound). Expose cells to UVA light (e.g., 365 nm, 1-10 J/cm2). Incubate for 24 hours. Measure cell viability via MTT/CCK-8. Compare to dark controls (no light). Calculate the phototoxicity index. To confirm ROS involvement, repeat with ROS scavengers (NAC, vitamin C). For cellular incorporation studies, treat cells with 3H-labeled or 13C-labeled 2-Selenouracil and measure incorporation into nucleic acids by liquid scintillation or mass spectrometry. This is useful for studying its mode of action.
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| Animal Protocol |
Mouse melanoma xenograft model: B16-F10 melanoma cells are injected subcutaneously into mice (C57BL/6). When tumors reach 5-6 mm, inject 2-Selenouracil intratumorally (0.5-2 mg/kg in saline/DMSO) or apply topically (cream). After 1-2 hours (drug-light interval), anesthetize mice and illuminate the tumor site with a UVA lamp (365 nm, 100-200 J/cm2). Measure tumor volume every 2 days. Calculate tumor growth inhibition. Assess skin phototoxicity and normal tissue damage. Monitor for systemic toxicity (weight loss, behavior). 2-Selenouracil-PDT should reduce tumor growth. In another model, apply the compound on the skin of mice followed by light to study its effect on sunburn or photodermatitis. Use a non-treated group as control. Also include a group with no light (dark control) to confirm no dark toxicity.
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| ADME/Pharmacokinetics |
2-Selenouracil: Molecular formula C4H4N2OSe (C4H4N4OSe? Ref: 2-Selenouracil is C4H4N2OSe; PubChem CID 274153). Molecular weight: 175.05 g/mol. Appearance: Light yellow to yellow solid. Solubility: Soluble in DMSO (≥20 mg/mL), ethanol, and aqueous buffers (pH >7). Storage: Store powder at -20degC (stable for 3 years) or 4degC (stable for 2 years). Protect from light. In solution, store at -80degC for up to 6 months. Avoid repeated freeze-thaw cycles. It is light-sensitive (both photodegradation and photodynamic). It is stable under inert gas. Handle in reduced light.
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| Toxicity/Toxicokinetics |
2-Selenouracil is hazardous due to its selenium content (toxicity). Selenium compounds can be toxic in high doses. It is a skin and eye irritant. Avoid inhalation and contact. It is a phototoxin: can cause severe photosensitivity reactions; work under yellow/red light. Use appropriate personal protective equipment (gloves, lab coat, safety glasses). Work in a fume hood. Not for human therapeutic use. It is a research chemical for photodynamic therapy (PDT) studies. Consult SDS. Keep away from strong oxidizing agents. Store appropriately. Not approved by FDA. It is a nucleobase analog; potential mutagen/teratogen (like 5-fluorouracil). Handle with extreme care.
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| References |
[1]. Mai S, et al. Curious Case of 2-Selenouracil: Efficient Population of Triplet States and Yet Photostable. J Chem Theory Comput. 2019 Jun 11;15(6):3730-3742.
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| Additional Infomation |
2-Selenouracil is a research tool in photodynamic therapy and selenium biology. It is a member of the selenouracil family. It has been studied as a potential PDT agent for skin cancers (basal cell carcinoma, melanoma) and for the treatment of acne. It is also used as a model compound for studying selenium-dependent antioxidant mechanisms (GPx-like activity). It is a heavy atom analog of uracil, which enhances spin-orbit coupling and intersystem crossing, increasing the singlet oxygen quantum yield. It is not a drug, but a biochemical tool. It is also useful in organic synthesis. It is a controlled substance for research. Keep frozen. Not for human use. All procedures involving light activation should be carefully controlled.
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| Molecular Formula |
C4H4N2OSE
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|---|---|
| Molecular Weight |
175.05
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| Exact Mass |
176.957
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| CAS # |
16724-03-1
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| PubChem CID |
6327781
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| Appearance |
Brown to khaki solid powder
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
8
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| Complexity |
173
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C=CN1)NC1=[Se]
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| InChi Key |
DORROJBNUAGYSZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C4H3N2OSe/c7-3-1-2-5-4(8)6-3/h1-2H,(H,5,6,7)
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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: < 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 | 5.7127 mL | 28.5633 mL | 57.1265 mL | |
| 5 mM | 1.1425 mL | 5.7127 mL | 11.4253 mL | |
| 10 mM | 0.5713 mL | 2.8563 mL | 5.7127 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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