| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
The primary biological target of 4-Phenoxyphenylboronic acid is the carbonic anhydrase enzyme family, specifically the fungal beta-carbonic anhydrases from pathogenic fungi such as Candida albicans and Cryptococcus neoformans. Boronic acid derivatives are known to inhibit carbonic anhydrases by coordinating with the zinc ion in the enzyme active site, forming a reversible tetrahedral adduct with the metal center. Beyond carbonic anhydrases, the compound may also interact with other zinc-dependent metalloenzymes due to the inherent metal-binding capacity of the boronic acid functionality. In synthetic chemistry applications, the compound serves as a substrate for palladium-catalyzed coupling reactions rather than as a direct pharmacological agent.
|
|---|---|
| ln Vitro |
4-Phenoxyphenylboronic is a reactant that can be utilized.
In vitro activity studies have focused on the compound's ability to inhibit fungal beta-carbonic anhydrases. Boronic acid derivatives, including 4-Phenoxyphenylboronic acid, demonstrate inhibitory activity against carbonic anhydrase enzymes by binding to the zinc ion within the active site. The compound's boronic acid moiety forms a reversible covalent interaction with the enzyme's metal center, leading to competitive inhibition. Structure-activity relationship studies suggest that the phenoxyphenyl substituent contributes to binding affinity through hydrophobic interactions with the enzyme's active site cavity. The compound has been evaluated in enzyme inhibition assays to determine its potency against fungal carbonic anhydrases, with potential applications in antifungal drug development. |
| ln Vivo |
In vivo activity data for 4-Phenoxyphenylboronic acid as a standalone therapeutic agent are not well documented in the literature. The compound is primarily utilized as a chemical reagent and synthetic intermediate rather than as a drug candidate for in vivo pharmacological evaluation. Boronic acid derivatives in general face challenges for in vivo application due to issues with metabolic stability and bioavailability. However, the compound's role in synthesizing biologically active aryl derivatives via Suzuki-Miyaura coupling suggests that its pharmacological effects would be observed through its incorporation into more complex molecular scaffolds rather than through the compound itself. In vivo studies would likely be conducted on the final drug products derived from this building block.
|
| Enzyme Assay |
For in vitro enzyme inhibition assays targeting carbonic anhydrases, the following protocol is typically employed: Purified recombinant beta-carbonic anhydrase from Candida albicans or Cryptococcus neoformans is incubated with varying concentrations of 4-Phenoxyphenylboronic acid (typically 0.01–100 µM) in assay buffer (e.g., 25 mM Tris-H2SO4, pH 7.4) at 25°C. The esterase activity of the enzyme is measured using 4-nitrophenyl acetate as substrate, monitoring absorbance at 400 nm over time. IC50 values are determined by fitting inhibition curves using nonlinear regression. Controls include enzyme without inhibitor and inhibitor without enzyme. Each concentration is tested in triplicate, and assays are repeated on at least three independent occasions to ensure reproducibility.
|
| Cell Assay |
For cell-based in vitro studies, 4-Phenoxyphenylboronic acid can be evaluated using fungal cell lines such as Candida albicans or Cryptococcus neoformans cultured in appropriate growth media (e.g., YPD broth for C. albicans) at 37°C with shaking. Cells are seeded in 96-well plates at a density of approximately 1–5 × 10⁴ cells per well and treated with serial dilutions of the compound (typically 0.1–1000 µM) for 24–72 hours. Cell viability is assessed using standard assays such as resazurin reduction, MTT, or CFU counting. The minimum inhibitory concentration (MIC) is determined as the lowest compound concentration that inhibits visible fungal growth. Positive controls (e.g., fluconazole) and vehicle controls (DMSO) are included in each experiment.
|
| Animal Protocol |
In vivo animal studies for 4-Phenoxyphenylboronic acid itself are not standard, as the compound is primarily a synthetic intermediate rather than a therapeutic agent. For evaluation of drug candidates synthesized from this building block, typical protocols would involve murine models of fungal infection. Immunocompromised mice (e.g., cyclophosphamide-treated) are inoculated intravenously or intraperitoneally with Candida albicans or Cryptococcus neoformans. Test compounds formulated in appropriate vehicles (e.g., PEG-400, saline with solubilizers) are administered via oral gavage, intravenous, or intraperitoneal routes at various dose levels (e.g., 1–100 mg/kg) once or twice daily for 3–14 days. Endpoints include survival rate, fungal burden in target organs (kidney, liver, lung), and histopathological analysis.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of 4-Phenoxyphenylboronic acid have not been extensively characterized due to its primary use as a chemical reagent. As a boronic acid-containing compound, it is expected to exhibit moderate aqueous solubility and the potential for reversible binding to serum proteins such as albumin and transferrin. Boronic acids are generally susceptible to oxidative degradation and may undergo metabolism via deboronation. The compound has a molecular weight of 214.02 g/mol and a calculated LogP of approximately 2.5–3.0, suggesting moderate lipophilicity. Its boiling point is predicted at 377.0°C. For drug discovery applications, the compound would require optimization to improve metabolic stability and bioavailability.
|
| Toxicity/Toxicokinetics |
Toxicological data for 4-Phenoxyphenylboronic acid are limited as the compound is primarily handled as a research chemical in laboratory settings. Standard safety precautions should be observed when handling boronic acid derivatives, including the use of personal protective equipment such as gloves, goggles, and lab coats. The compound may cause skin, eye, and respiratory tract irritation upon exposure. Inhalation of dust or contact with skin should be avoided. In case of accidental exposure, affected areas should be rinsed thoroughly with water. The compound should be stored in a cool, dry place away from strong oxidizing agents and moisture. Comprehensive toxicological profiling, including acute toxicity, genotoxicity, and reproductive toxicity studies, has not been reported.
|
| Additional Infomation |
4-Phenoxyphenylboronic acid is primarily a chemical research tool rather than an approved pharmaceutical drug. Its main application lies in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl compounds, which are common structural motifs in numerous pharmaceuticals and agrochemicals. The compound has been investigated as a carbonic anhydrase inhibitor, particularly targeting fungal beta-carbonic anhydrases from C. albicans and C. neoformans, suggesting potential antifungal applications. No clinical trials or regulatory approvals have been documented for this compound as a therapeutic agent. The compound is commercially available as a research-grade chemical with purity specifications typically ≥95%, and is supplied in various quantities for laboratory use.
|
| Molecular Formula |
C12H11BO3
|
|---|---|
| Molecular Weight |
214.02
|
| Exact Mass |
214.08
|
| CAS # |
51067-38-0
|
| PubChem CID |
2734377
|
| Appearance |
White to off-white solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
377.0±44.0 °C at 760 mmHg
|
| Melting Point |
141-145 °C(lit.)
|
| Flash Point |
181.8±28.4 °C
|
| Vapour Pressure |
0.0±0.9 mmHg at 25°C
|
| Index of Refraction |
1.605
|
| LogP |
3.58
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
16
|
| Complexity |
196
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O(C1C([H])=C([H])C([H])=C([H])C=1[H])C1C([H])=C([H])C(B(O[H])O[H])=C([H])C=1[H]
|
| InChi Key |
KFXUHRXGLWUOJT-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C12H11BO3/c14-13(15)10-6-8-12(9-7-10)16-11-4-2-1-3-5-11/h1-9,14-15H
|
| Chemical Name |
(4-phenoxyphenyl)boronic acid
|
| 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 | 4.6725 mL | 23.3623 mL | 46.7246 mL | |
| 5 mM | 0.9345 mL | 4.6725 mL | 9.3449 mL | |
| 10 mM | 0.4672 mL | 2.3362 mL | 4.6725 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
