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| Targets |
The target of 4-(Trifluoromethyl)umbelliferone is cytochrome P450 (CYP) enzymes, particularly those in the liver. Its mechanism of action is as a fluorogenic substrate for these enzymes. When CYP enzymes metabolize the compound, the fluorescent product is released. The increase in fluorescence is proportional to the enzyme activity, allowing for the measurement of CYP activity in vitro. This makes it a valuable tool for studying drug metabolism and for screening for CYP inhibitors.
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| ln Vitro |
In vitro, 4-(Trifluoromethyl)umbelliferone is a fluorescent probe substrate for rat liver cytochrome P450 enzymes. Its fluorescence is pH-dependent. It serves as a fluorogenic substrate for various CYP enzymes. The compound is used in enzyme assays to measure CYP activity and to screen for compounds that inhibit or induce these enzymes. Its pH-dependent fluorescence can also be exploited for sensing pH changes in biological samples.
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| ln Vivo |
In vivo activity of 4-(Trifluoromethyl)umbelliferone is not typically studied, as it is a probe used in in vitro enzyme assays. However, the compound could potentially be used to measure CYP activity in vivo, for example, by administering it to animals and monitoring the appearance of the fluorescent product in the blood or bile. Specific in vivo data is not available.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays using 4-(Trifluoromethyl)umbelliferone are based on its role as a fluorogenic substrate for CYP enzymes. A standard protocol: liver microsomes or recombinant CYP enzymes are incubated with 4-(Trifluoromethyl)umbelliferone in a buffer containing NADPH (a cofactor for CYP enzymes). The reaction is incubated at 37°C for a defined period. The reaction is stopped, and the fluorescence of the product is measured using a fluorometer with excitation at 360 nm and emission at 460 nm. The enzyme activity is calculated from the rate of fluorescence increase.
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| Cell Assay |
In vitro cell-based assays for 4-(Trifluoromethyl)umbelliferone are not common, as it is primarily used in cell-free enzyme assays. However, it could be used to measure CYP activity in cultured cells. A standard protocol: cells (e.g., hepatocytes) are incubated with the compound in culture medium. The fluorescence of the medium is measured over time to assess the metabolism of the compound by cellular CYP enzymes. This approach can be used to study the effects of drugs or other compounds on CYP activity in cells.
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| Animal Protocol |
In vivo animal experiments for 4-(Trifluoromethyl)umbelliferone are not typically performed. However, the compound could be used to assess hepatic CYP activity in vivo. For example, the compound could be administered to rats, and the appearance of the fluorescent metabolite in the blood or bile could be monitored over time. This would provide a measure of hepatic CYP activity. Such studies are more common in drug development to assess the potential for drug-drug interactions.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
7-Hydroxy-4-trifluoromethylcoumarin is a known human metabolite of 7-ethoxy-4-trifluoromethylcoumarin, 7-methoxy-4-trifluoromethylcoumarin, 7-benzyloxy-4-trifluoromethylcoumarin, zinc 02949712, and 4-(trifluoromethyl)-7-[2,5-bis(trifluoromethyl)benzyloxy]coumarin. Pharmacokinetic properties of 4-(Trifluoromethyl)umbelliferone have not been characterized. The compound is a small, lipophilic molecule (MW 230.14 g/mol). It is likely to be absorbed if administered orally and to be metabolized by CYP enzymes. Its fluorescence is pH-dependent, which may affect its detection in different biological environments. The compound is typically stored as a solid at room temperature. |
| Toxicity/Toxicokinetics |
Toxicity data for 4-(Trifluoromethyl)umbelliferone is limited. As a chemical reagent, it should be handled with standard laboratory precautions. The compound contains a trifluoromethyl 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 |
4-(Trifluoromethyl)umbelliferone is a fluorescent probe substrate for rat hepatic cytochrome P450 enzymes. Its fluorescence is pH-dependent. It serves as a fluorogenic substrate for various CYP enzymes. It is also known as 7-Hydroxy-4-(trifluoromethyl)coumarin. 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 |
C10H5F3O3
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| Molecular Weight |
230.1401
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| Exact Mass |
230.019
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| CAS # |
575-03-1
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| PubChem CID |
5375667
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| Appearance |
Pale purple to purple solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
311.4±42.0 °C at 760 mmHg
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| Melting Point |
178-180 °C(lit.)
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| Flash Point |
142.2±27.9 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.546
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| LogP |
2.88
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
16
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| Complexity |
335
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
CCKWMCUOHJAVOL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H5F3O3/c11-10(12,13)7-4-9(15)16-8-3-5(14)1-2-6(7)8/h1-4,14H
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| Chemical Name |
7-hydroxy-4-(trifluoromethyl)chromen-2-one
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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 (~434.52 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (5.43 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 12.5 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: 1.25 mg/mL (5.43 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.3452 mL | 21.7259 mL | 43.4518 mL | |
| 5 mM | 0.8690 mL | 4.3452 mL | 8.6904 mL | |
| 10 mM | 0.4345 mL | 2.1726 mL | 4.3452 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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