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| Targets |
2-Biphenylboronic acid (2-BPBA) has demonstrated diverse biological activities, particularly as an inhibitor of β-lactamases, enzymes produced by bacteria that confer resistance to β-lactam antibiotics. It shows inhibitory activity against AmpC (IC₅₀ = 0.5 µM), KPC-2 (IC₅₀ = 0.8 µM), and OXA-24 (IC₅₀ = 5.0 µM). The compound also interferes with auxin transport proteins in plants, affecting organogenesis and leaf development.
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| ln Vitro |
2-Biphenylboronic acid is a substrate for the cross-coupling of benzyl acetate with palladium to produce diarylmethane. It is a reactant in the Suzuki-Miyaura cross-coupling reactions of quinoline carboxylates, alkenyl tosylate and mesylate esters, dibromovinyl precursors, and aryl halides. It is engaged in hydroxylation to phenols, oxidative coupling with alkynes, and intramolecular Friedel-Crafts alkylation for the production of chiral tetralin.
In vitro, 2-biphenylboronic acid exhibits antimicrobial activity by inhibiting β-lactamases. It has demonstrated significant free radical scavenging ability in antioxidant assays, with a DPPH scavenging activity IC₅₀ of 0.14 µg/mL and a CUPRAC A₀.₅ of 1.73 µg/mL. The compound has been evaluated against carbapenem-resistant Enterobacteriaceae strains, showing enhanced activity when combined with meropenem. In plant models, it induces phenocopies affecting organogenesis and leaf development. |
| ln Vivo |
In vivo data for 2-biphenylboronic acid as a therapeutic agent are limited. The compound has been studied in plant models such as Arabidopsis thaliana and Solanum lycopersicum, where treatment with boronic acids resulted in specific developmental alterations mimicking genetic mutations related to auxin signaling pathways. For antimicrobial applications, the compound is primarily evaluated in vitro. Specific in vivo pharmacokinetic and pharmacodynamic data for this compound are not well-documented.
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| Enzyme Assay |
For in vitro enzyme inhibition assays, 2-biphenylboronic acid is evaluated against β-lactamases such as AmpC, KPC-2, and OXA-24. Enzyme activity is measured spectrophotometrically using a chromogenic substrate (e.g., nitrocefin). The compound (0.01-100 µM) is pre-incubated with the enzyme for 5-10 minutes at 25°C before substrate addition. IC₅₀ values are calculated from dose-response curves. The compound shows IC₅₀ values of 0.5 µM for AmpC, 0.8 µM for KPC-2, and 5.0 µM for OXA-24.
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| Cell Assay |
For in vitro cell-based experiments, 2-biphenylboronic acid can be evaluated for antimicrobial activity against bacterial cell lines. Bacteria are cultured in appropriate media and treated with the compound at various concentrations (typically 0.1-100 µg/mL) for 18-24 hours. Minimum inhibitory concentration (MIC) is determined using broth microdilution methods. The compound can also be tested in combination with β-lactam antibiotics to assess synergistic effects.
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| Animal Protocol |
In vivo animal studies for 2-biphenylboronic acid are not well-documented. For antimicrobial drug candidates derived from this building block, efficacy studies would typically be performed in mouse models of bacterial infection. Standard in vivo protocols involve administration to rodents via oral gavage or intraperitoneal injection, with measurement of bacterial burden in target organs. Specific protocols for this compound are not available in the public literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2-biphenylboronic acid are not extensively characterized. The compound has a molecular weight of 198.03 g/mol, which is within the favorable range for oral bioavailability. The biphenyl structure and boronic acid group suggest moderate lipophilicity. As a boronic acid, it may be subject to metabolic oxidation. Empirical pharmacokinetic data (half-life, clearance, bioavailability) are not available in the public literature.
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| Toxicity/Toxicokinetics |
2-Biphenylboronic acid is a research chemical and should be handled with appropriate laboratory safety precautions. As a boronic acid derivative, it may cause skin and eye irritation. The compound should be stored as a powder at -20°C for up to 3 years or in solvent at -80°C for up to 1 year. Specific LD₅₀ values, acute toxicity classifications, and chronic toxicity data are not available in the public literature. Standard safety practices include the use of personal protective equipment.
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| Additional Infomation |
2-Biphenylboronic acid (2-BPBA, CAS 4688-76-0) is primarily a research-grade chemical intermediate and biochemical reagent, not an FDA-approved pharmaceutical drug. Its primary applications are in organic synthesis as a reagent for Suzuki-Miyaura coupling reactions and as a sulfonylation reagent for drug discovery. The compound has demonstrated antimicrobial activity by inhibiting β-lactamases and antioxidant properties. No clinical trials or approved indications exist for this compound.
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| Molecular Formula |
C12H11BO2
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| Molecular Weight |
198.03
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| Exact Mass |
198.085
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| CAS # |
4688-76-0
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| PubChem CID |
4589187
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
404.0±38.0 °C at 760 mmHg
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| Melting Point |
167-172 °C(lit.)
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| Flash Point |
198.1±26.8 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.610
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| LogP |
3.35
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
15
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| Complexity |
190
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])B(C1=C([H])C([H])=C([H])C([H])=C1C1C([H])=C([H])C([H])=C([H])C=1[H])O[H]
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| InChi Key |
HYCYKHYFIWHGEX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H11BO2/c14-13(15)12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,14-15H
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| Chemical Name |
(2-phenylphenyl)boronic acid
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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 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.) |
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.0497 mL | 25.2487 mL | 50.4974 mL | |
| 5 mM | 1.0099 mL | 5.0497 mL | 10.0995 mL | |
| 10 mM | 0.5050 mL | 2.5249 mL | 5.0497 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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