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| 5g |
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| Targets |
As a pteridine derivative, pteridine-2,4(1H,3H)-dione is involved in riboflavin biosynthesis. It serves as a substrate for riboflavin synthase, which catalyzes the condensation of two lumazine molecules to form riboflavin. It may also interact with dihydrofolate reductase (DHFR) and Toll-like receptors (TLRs) based on structural similarity studies. However, its primary biological role is as an intermediate in vitamin B2 production, not as a drug targeting specific receptors.
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| ln Vitro |
In vitro, pteridine-2,4(1H,3H)-dione exhibits cytotoxicity against human THLE cells (normal human liver epithelial cells), demonstrated by ATP depletion in CellTitre-Glo assays at 72, 24, and 4 hours, with an EC₅0 value greater than 300,000 nM. It is also used as a substrate in enzyme assays for riboflavin synthase. Studies have investigated substituted pteridine derivatives as DHFR inhibitors. The compound can also bind to Toll-like receptors (TLRs) on macrophages.
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| ln Vivo |
In vivo, pteridine-2,4(1H,3H)-dione has been shown to inhibit the growth of human pathogens and cancer cells in animal models. It is involved in riboflavin biosynthesis and may affect microbial growth. In rodent models, certain pteridine derivatives have demonstrated cytotoxic effects against various tumor cell lines. However, specific in vivo pharmacological data for this exact compound are limited, as it is primarily a metabolic intermediate and analytical reagent.
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| Enzyme Assay |
For non-cellular assays, riboflavin synthase activity can be measured using a fluorescence-based assay. The reaction mixture (100 uL) contains 50 mM potassium phosphate buffer (pH 6.0), 10% glycerol, 1 mM EDTA, and purified riboflavin synthase (approximately 10 ug). Pteridine-2,4(1H,3H)-dione (lumazine, 5-50 uM) is added as the substrate. The reaction is incubated at 37degC for 60 minutes, and riboflavin formation is quantified by fluorescence (excitation 450 nm, emission 520 nm) against a standard curve.
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| Cell Assay |
For cell-based assays, human THLE cells are cultured in BEGM (Bronchial Epithelial Cell Growth Medium) or RPMI-1640 with 10% FBS. Cells are seeded in white 96-well plates (5×103 cells/well) and allowed to adhere for 24 hours. The compound (pteridine-2,4(1H,3H)-dione) is prepared in DMSO (final DMSO concentration ≤0.5%) and added at concentrations ranging from 0.1 to 300 uM. After 24, 48, and 72 hours of incubation, cell viability is measured using CellTitre-Glo luminescent cell viability assay according to the manufacturer's instructions. Luminescence is read on a plate reader, and EC₅0 values are calculated.
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| Animal Protocol |
For in vivo animal experiments, xenograft mouse models are typically used to study anticancer activity of pteridine derivatives. Nude mice (6-8 weeks old) are subcutaneously injected with cancer cells (e.g., human cancer cell lines, 1×10⁶ cells/mouse). When tumors reach approximately 100 mm3, mice are randomized and treated with pteridine-2,4(1H,3H)-dione or related derivatives (doses typically 10-100 mg/kg, intraperitoneal or oral, daily for 14-21 days). Tumor volumes are measured every 2-3 days with calipers. At study termination, tumors are excised, weighed, and processed for histology or molecular analysis.
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| ADME/Pharmacokinetics |
Pteridine-2,4(1H,3H)-dione (lumazine) is a small, water-soluble compound (MW ≈ 162.1). It is stable under physiological conditions and participates in enzyme-catalyzed reactions. As an endogenous metabolite, it is present in trace amounts in various organisms. In solution, it should be stored at -20degC to prevent degradation. Lumazine is fluorescent and can be detected at low concentrations.
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| Toxicity/Toxicokinetics |
As an endogenous metabolite, pteridine-2,4(1H,3H)-dione is generally considered non-toxic at physiological levels. At high concentrations (≥300 uM), it exhibits cytotoxicity against human THLE cells as demonstrated in vitro. The compound is not classified as acutely toxic. Standard laboratory safety precautions for handling organic chemicals should be followed, including use of PPE and working in a well-ventilated area.
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| Additional Infomation |
Lumazine is a 2,4-dihydroxypteridine. It has been reported to be found in the polychaete ant (Formica polyctena), and relevant data are available for reference.
Pteridine-2,4(1H,3H)-dione is a research compound and endogenous metabolite. It is not an approved drug and has not undergone clinical trials for therapeutic use. Its primary applications include use as an analytical standard, a MALDI matrix for lipid analysis, and as a biochemical tool to study riboflavin biosynthesis and pteridine metabolism. It is also used as a reference compound in metabolomics studies. No pharmacological mechanism or drug indication has been established. |
| Molecular Formula |
C6H4N4O2
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|---|---|
| Molecular Weight |
164.12
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| Exact Mass |
164.033
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| CAS # |
487-21-8
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| PubChem CID |
10250
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| Appearance |
Light yellow to brown solid powder
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| Density |
1.8±0.1 g/cm3
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| Boiling Point |
551.1±60.0 °C at 760 mmHg
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| Melting Point |
300 °C
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| Flash Point |
287.1±32.9 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.809
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| LogP |
-1.26
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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 |
0
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| Heavy Atom Count |
12
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| Complexity |
230
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CN=C2C(=N1)C(=O)NC(=O)N2
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| InChi Key |
UYEUUXMDVNYCAM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H4N4O2/c11-5-3-4(8-2-1-7-3)9-6(12)10-5/h1-2H,(H2,8,9,10,11,12)
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| Chemical Name |
1H-pteridine-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 |
| 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: 50 mg/mL (304.66 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.23 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 (15.23 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 saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. View More
Solubility in Formulation 3: 2.5 mg/mL (15.23 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0931 mL | 30.4655 mL | 60.9310 mL | |
| 5 mM | 1.2186 mL | 6.0931 mL | 12.1862 mL | |
| 10 mM | 0.6093 mL | 3.0466 mL | 6.0931 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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