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| Targets |
4-Phenylimidazole is a synthetic intermediate and catalyst that interacts with heme-containing proteins. The compound has been used to investigate protein-ligand interactions in cytochrome P450 and as a heme ligand during crystallization of recombinant indoleamine 2,3-dioxygenase. Binding of 4-phenylimidazole to malonic acid inhibits the reaction mechanism of the Krebs cycle and inhibits cancer cell proliferation. Its primary applications are as a catalyst in chemical reactions and as a research tool for studying heme protein interactions.
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| ln Vitro |
In vitro, 4-phenylimidazole is used as a biochemical reagent and organic compound for biomedical research. It is known for its role as a catalyst in various chemical reactions, particularly in the synthesis of pharmaceuticals and agrochemicals. The compound inhibits cancer cell proliferation. Cellular assays may evaluate its anticancer activity, its effects on heme proteins, or its catalytic properties. The compound's imidazole scaffold allows for various chemical transformations.
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| ln Vivo |
In vivo, 4-phenylimidazole has been shown to inhibit cancer cell proliferation, suggesting potential therapeutic applications. The compound is classified for research use only and is not intended for human or veterinary therapeutic applications. Its ability to interact with heme proteins and inhibit the Krebs cycle suggests potential for further development. Specific in vivo data for therapeutic applications is limited.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 4-phenylimidazole typically evaluate its interaction with heme-containing proteins. A standard protocol involves incubating the compound with purified cytochrome P450 or other heme proteins in appropriate buffer systems. The compound is dissolved in DMSO and diluted to working concentrations. Binding affinity is assessed using UV-Vis spectroscopy (measuring changes in the Soret band) or other techniques. Enzyme activity is measured by quantifying substrate conversion. IC₅₀ or Kd values are calculated from dose-response curves.
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| Cell Assay |
Cellular assays for 4-phenylimidazole typically evaluate its anticancer activity. A standard protocol involves culturing cancer cell lines in growth medium at 37°C with 5% CO₂. Cells are treated with varying concentrations of the compound for 24-72 hours. Cell viability is assessed using MTT or similar assays. Apoptosis and cell cycle analysis are performed using flow cytometry. The compound's effects on the Krebs cycle and cellular metabolism can be evaluated by measuring metabolic intermediates. IC₅₀ values are calculated from dose-response curves.
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| Animal Protocol |
In vivo animal studies for 4-phenylimidazole are not standard, as it is primarily a research reagent. The compound is classified for research use only and is not intended for human or veterinary applications. Any animal studies would be limited to evaluating its anticancer efficacy or its effects on heme proteins. The compound's primary value lies in its use as a research tool for studying heme protein interactions and as a catalyst. Specific in vivo protocols are not available in the public literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 4-phenylimidazole is limited, as it is primarily a research reagent. The compound has a molecular weight of 144.17 g/mol and a molecular formula of C₉H₈N₂. It is a solid at room temperature with a melting point of 128-131°C. As an imidazole, it may undergo metabolic oxidation and conjugation. Specific ADME data is not available. The compound is stored in a dry, cool place.
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| Toxicity/Toxicokinetics |
4-Phenylimidazole is classified for research use only and is not intended for human or veterinary applications. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound should be stored in a dry, cool place away from incompatible materials. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed. No specific LD₅₀ values are available in the public domain.
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| Additional Infomation |
Tautomers; Cytochrome P450 14α-sterol demethylase, CYP51 antagonist
4-Phenylimidazole (5-Phenyl-1H-imidazole, CAS 670-95-1) is a biochemical reagent with the molecular formula C₉H₈N₂. It is an imidazole derivative used as a catalyst in pharmaceutical and agrochemical synthesis and has antitermite activity. It inhibits cancer cell proliferation and is used to study protein-ligand interactions in heme proteins. The compound is classified as a research-use-only compound not intended for diagnostic or therapeutic purposes. |
| Molecular Formula |
C9H8N2
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|---|---|
| Molecular Weight |
144.17
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| Exact Mass |
144.068
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| CAS # |
670-95-1
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| Related CAS # |
40864-48-0 (mono-hydrochloride)
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| PubChem CID |
69590
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| Appearance |
Solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
379.8±11.0 °C at 760 mmHg
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| Melting Point |
128-131 °C(lit.)
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| Flash Point |
213.0±5.7 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.603
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| LogP |
1.46
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
119
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C(C=C1)C2=CN=CN2
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| InChi Key |
XHLKOHSAWQPOFO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H8N2/c1-2-4-8(5-3-1)9-6-10-7-11-9/h1-7H,(H,10,11)
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| Chemical Name |
5-phenyl-1H-imidazole
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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) |
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 | 6.9363 mL | 34.6813 mL | 69.3626 mL | |
| 5 mM | 1.3873 mL | 6.9363 mL | 13.8725 mL | |
| 10 mM | 0.6936 mL | 3.4681 mL | 6.9363 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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