| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| Other Sizes |
| Targets |
The primary target of 3-Cyanoumbelliferone is macrophage migration inhibitory factor (MIF) tautomerase, an enzyme involved in inflammatory responses. Its mechanism of action as an inhibitor involves binding to the active site of MIF tautomerase, thereby inhibiting its enzymatic activity. This inhibition can modulate inflammatory pathways. As a fluorescent dye, its mechanism is based on its coumarin chromophore, which absorbs light and emits fluorescence, allowing it to be used as a probe for various applications.
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| ln Vitro |
In vitro, 3-Cyanoumbelliferone is used as a molecular probe and fluorescent dye. It is a macrophage migration inhibitory factor (MIF) tautomerase inhibitor with a Ki of 2.9 μM. As a coumarin analogue, it exhibits fluorescence properties that make it suitable for use as a probe in biological assays. Its ability to inhibit MIF tautomerase makes it a valuable tool for studying the role of MIF in inflammation and other disease processes.
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| ln Vivo |
In vivo activity of 3-Cyanoumbelliferone is not well-documented. As a MIF tautomerase inhibitor, it could potentially have anti-inflammatory effects in vivo. However, specific data on its efficacy in animal models of inflammation is not available. Its use as a fluorescent probe may also be applicable in vivo for imaging purposes, depending on its pharmacokinetic properties and tissue distribution.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays for 3-Cyanoumbelliferone typically involve measuring its inhibition of MIF tautomerase activity. A standard protocol: recombinant MIF tautomerase is incubated with a substrate (e.g., D-dopachrome) in a buffer. The enzyme activity is measured by monitoring the change in absorbance at a specific wavelength. Various concentrations of 3-Cyanoumbelliferone are added to the reaction mixture, and the inhibition of enzyme activity is determined. The Ki value (2.9 μM) is calculated from the dose-response curve.
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| Cell Assay |
In vitro cell-based assays for 3-Cyanoumbelliferone could involve studying its effects on MIF-mediated signaling. A standard protocol: cells (e.g., macrophages) are treated with 3-Cyanoumbelliferone and stimulated with MIF or other inflammatory stimuli. The activation of downstream signaling pathways (e.g., ERK, AKT) is assessed by Western blotting. The production of inflammatory cytokines (e.g., TNF-α, IL-6) is measured by ELISA. The compound's effects on cell migration and proliferation can also be assessed. These assays help to elucidate the cellular effects of MIF inhibition.
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| Animal Protocol |
In vivo animal experiments for 3-Cyanoumbelliferone have not been described in the literature. For MIF inhibitors, a standard in vivo study would use a mouse model of inflammation or autoimmune disease. For example, mice could be treated with 3-Cyanoumbelliferone in a model of sepsis, arthritis, or colitis. The severity of inflammation would be assessed by measuring clinical scores, inflammatory markers, and histopathology. Such studies would evaluate the compound's potential as an anti-inflammatory agent.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
3-Cyano-7-hydroxycoumarin is a known human metabolite of 3-cyano-7-ethoxycoumarin and 3-cyano-7-methoxycoumarin. Pharmacokinetic properties of 3-Cyanoumbelliferone have not been characterized. Its molecular weight is 187.15 g/mol. The compound is a small, lipophilic molecule that is likely to be absorbed if administered orally. Its fluorescence properties are pH-dependent, which may affect its detection in different biological environments. The compound is typically stored at room temperature. |
| Toxicity/Toxicokinetics |
Toxicity data for 3-Cyanoumbelliferone is limited. As a chemical reagent, it should be handled with standard laboratory precautions. The compound contains a nitrile group, which may pose some toxicity concerns. Inhalation, ingestion, and skin contact should be avoided. Appropriate personal protective equipment should be worn.
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| References | |
| Additional Infomation |
3-Cyanoumbelliferone is a coumarin analogue used as a molecular probe and fluorescent dye. It is also a macrophage migration inhibitory factor (MIF) tautomerase inhibitor with a Ki of 2.9 μM. It is used in research to study MIF function and as a fluorescent probe. It is not a drug and has no clinical use or approval status. It is commercially available from chemical suppliers for research purposes only.
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| Molecular Formula |
C10H5NO3
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|---|---|
| Molecular Weight |
187.1516
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| Exact Mass |
187.027
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| CAS # |
19088-73-4
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| PubChem CID |
5393173
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| Appearance |
Yellow to orange solid powder
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| Density |
1.5 g/cm3
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| Boiling Point |
436.6ºC at 760 mmHg
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| Melting Point |
≥250ºC(lit.)
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| Flash Point |
217.8ºC
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| Vapour Pressure |
3.13E-08mmHg at 25°C
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| Index of Refraction |
1.667
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| LogP |
1.37
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
14
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| Complexity |
339
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
IJQYTHQDUDCJEQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H5NO3/c11-5-7-3-6-1-2-8(12)4-9(6)14-10(7)13/h1-4,12H
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| Chemical Name |
7-hydroxy-2-oxochromene-3-carbonitrile
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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 (e.g. under nitrogen), 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 5.3433 mL | 26.7165 mL | 53.4331 mL | |
| 5 mM | 1.0687 mL | 5.3433 mL | 10.6866 mL | |
| 10 mM | 0.5343 mL | 2.6717 mL | 5.3433 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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