| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Phenyl benzoate has been reported to target the C-C chemokine receptor type 5 (CCR5) as an antagonist. CCR5 is a chemokine receptor expressed on the surface of T cells and macrophages and is a co-receptor for HIV-1 entry. Phenyl benzoate is a CCR5 antagonist. Additionally, phenyl benzoate is a chloride transport blocker and inhibits Cl--dependent glutamate accumulation into vesicles. It may have other targets related to its antimicrobial and preservative activities.
|
|---|---|
| ln Vitro |
Rat brain membranes are inhibited from binding L-[3H]Glu (100 nM) in both Ca2+/Cl-dependent and -independent ways by phenol benzoate (DPC) (0.1 μM-1 mM; 15 min)[1].
In vitro, Phenyl benzoate acts as a CCR5 antagonist and has been shown to bind to a receptor on the surface of cells, inhibiting its activity. It has been shown to inhibit the production of pro-inflammatory cytokines such as IL-1beta and TNF-alpha in primary cells from human erythrocytes. Phenyl benzoate also functions as a chloride transport blocker and inhibits Cl--dependent glutamate accumulation into vesicles. It has been shown to have potential therapeutic effects on cell function and signal transduction. It has been found to inhibit the proliferation of cancer cells and induce apoptosis. |
| ln Vivo |
Phenyl benzoate is a CCR5 antagonist and has been used in research on autoimmune diseases. It binds to a receptor on the surface of cells and inhibits the activity of this receptor, which leads to inflammation reduction. Phenyl benzoate has been shown to inhibit the production of inflammatory cytokines such as IL-1beta and TNF-alpha in primary cells. Specific in vivo efficacy data in animal models of HIV, inflammation, or autoimmune diseases is limited. However, the compound may be used as a starting material for the synthesis of more potent CCR5 antagonists.
|
| Enzyme Assay |
The specific protocol for assessing CCR5 antagonism uses a radioligand binding assay. Membranes from CHO cells stably expressing human CCR5 are incubated with [¹2⁵I]-MIP-1alpha or [¹2⁵I]-RANTES (a radiolabeled chemokine ligand) in binding buffer (25 mM HEPES, pH 7.4, 0.5% BSA, 5 mM MgCl2, 1 mM CaCl2) for 60 minutes at room temperature. Varying concentrations of Phenyl benzoate (0.01-1000 uM) are added to compete with the radioligand. Non-specific binding is determined in the presence of 10 uM unlabeled MIP-1alpha. Bound and free radioligands are separated by vacuum filtration through GF/B filters pre-soaked in 0.3% PEI. Filters are washed and counted. IC50 values are calculated from competition curves. For chloride channel blocking activity, a [3⁶Cl]- uptake assay using membrane vesicles can be used.
|
| Cell Assay |
For in vitro cellular assays, primary human erythrocytes are isolated from whole blood and cultured. Cells are treated with Phenyl benzoate (1-1000 uM) for 24-48 hours. Cell culture supernatants are collected, and the levels of pro-inflammatory cytokines (TNF-alpha, IL-1beta, IL-6) are measured by ELISA. Alternatively, peripheral blood mononuclear cells (PBMCs) are stimulated with LPS (1 ug/mL) in the presence or absence of Phenyl benzoate. Cell viability is assessed using the MTT assay to ensure that the anti-inflammatory effects are not due to cytotoxicity. The inhibition of cancer cell proliferation can be assessed using MTT or CellTiter-Glo assays on various cancer cell lines.
|
| Animal Protocol |
An in vivo protocol for a CCR5 antagonist such as Phenyl benzoate would involve a mouse model of HIV infection (e.g., hu-PBL-SCID mice or HIV-1-infected humanized mice). Phenyl benzoate would be administered orally at doses of 10-100 mg/kg daily for 2-4 weeks. Viral load (HIV-1 RNA copies/mL) in plasma would be measured by qRT-PCR. CD4+ T-cell counts in the blood would be measured by flow cytometry. In an inflammatory disease model, such as collagen-induced arthritis (CIA) in DBA/1J mice, Phenyl benzoate would be administered orally at doses of 10-100 mg/kg daily for 6-8 weeks. Arthritis scores, paw swelling, and histological assessment of joint inflammation would be performed.
|
| ADME/Pharmacokinetics |
Specific pharmacokinetic data for Phenyl benzoate is not available. As a small lipophilic ester, it is expected to have moderate oral bioavailability and good cell membrane permeability. It is poorly soluble in water but soluble in organic solvents such as DMSO and ethanol. Phenyl benzoate is likely to be hydrolyzed by esterases in the gastrointestinal tract and liver, releasing phenol and benzoic acid as metabolites. The terminal half-life is expected to be short due to rapid hydrolysis. Excretion is likely in the urine as conjugated metabolites (e.g., phenol glucuronide and benzoic acid glycine conjugate, hippuric acid).
|
| Toxicity/Toxicokinetics |
Specific toxicology data for Phenyl benzoate is limited. It is used as a preservative in cosmetic products at low concentrations, indicating low acute toxicity. Phenol and benzoic acid are the major hydrolysis products of Phenyl benzoate, and both have established safety profiles. Phenol is toxic at high concentrations, causing CNS depression, respiratory failure, and skin burns. Benzoic acid is generally recognized as safe (GRAS) as a food preservative at concentrations up to 0.1%. Standard safety assessment would include acute oral toxicity studies in rodents to determine the LD50, and dermal/eye irritation studies.
|
| References |
|
| Additional Infomation |
Benzyl benzoate is a benzoic acid ester obtained by condensing phenol and benzoic acid.
Phenyl benzoate is a research-grade chemical and is not approved for clinical use. Its molecular formula is C13H10O2 with a molecular weight of 198.22 and a purity of >98%. It is a CCR5 antagonist and a chloride transport blocker. Phenyl benzoate is also used as a preservative in cosmetic products and as a synthetic intermediate in the production of polyimides, optical components (lenses), and other specialty chemicals. The compound is a solid at room temperature (melting point 68-70degC, boiling point 298-299degC) and is stable under normal storage conditions. It is stored at room temperature in a cool, dark place (<15degC). |
| Molecular Formula |
C13H10O2
|
|---|---|
| Molecular Weight |
198.22
|
| Exact Mass |
198.068
|
| CAS # |
93-99-2
|
| PubChem CID |
7169
|
| Appearance |
White to off-white solid powder
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
314.0±11.0 °C at 760 mmHg
|
| Melting Point |
68-70 °C(lit.)
|
| Flash Point |
128.9±16.7 °C
|
| Vapour Pressure |
0.0±0.7 mmHg at 25°C
|
| Index of Refraction |
1.585
|
| LogP |
3.59
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
15
|
| Complexity |
201
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=CC=C(C=C1)C(=O)OC2=CC=CC=C2
|
| InChi Key |
FCJSHPDYVMKCHI-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C13H10O2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H
|
| Chemical Name |
phenyl benzoate
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| 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
|
|---|---|
| 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 | 5.0449 mL | 25.2245 mL | 50.4490 mL | |
| 5 mM | 1.0090 mL | 5.0449 mL | 10.0898 mL | |
| 10 mM | 0.5045 mL | 2.5224 mL | 5.0449 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
