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| Targets |
2-Naphthylboronic acid has been reported to act as an inhibitor of the Staphylococcus aureus NorA efflux pump. The compound was found to potentiate ciprofloxacin activity by a 4-fold increase at concentrations ranging at 4-8 μg/ml against S. aureus 1199B. The boronic acid functionality allows for reversible covalent bonding with diols and other nucleophiles, which may contribute to its biological activity. The compound's ability to inhibit efflux pumps makes it valuable as a potential adjuvant to antibiotic therapy. Its primary applications are in organic synthesis and as a research tool for studying efflux pump inhibition.
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| ln Vitro |
In vitro, 2-naphthylboronic acid is used as a biochemical reagent and organic compound for biomedical research. It is used in enantioselective rhodium-catalyzed addition reactions. The compound has been reported to inhibit the S. aureus NorA efflux pump and potentiate ciprofloxacin activity. Cellular assays typically evaluate its antibacterial activity, efflux pump inhibition, or cytotoxicity. The compound's boronic acid functionality allows for various chemical transformations, including Suzuki-Miyaura cross-coupling reactions, making it valuable for organic synthesis and medicinal chemistry.
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| ln Vivo |
In vivo data for 2-naphthylboronic acid is limited, as it is primarily a research reagent and synthetic intermediate. The compound is classified for research use only and is not intended for human or veterinary therapeutic applications. Its ability to inhibit bacterial efflux pumps suggests potential as an antibiotic adjuvant, though specific in vivo efficacy data is not available. The compound's primary value lies in its use as a research tool for studying efflux pump inhibition and as a building block for organic synthesis. Specific in vivo data for therapeutic applications is not available in the public literature.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 2-naphthylboronic acid typically evaluate its activity as an efflux pump inhibitor or its binding to bacterial proteins. A standard assay protocol involves incubating the compound with bacterial cells expressing NorA efflux pump in appropriate buffer systems containing a fluorescent substrate (e.g., ethidium bromide). The compound is dissolved in DMSO and diluted to working concentrations (typically 1-100 μM). Efflux pump activity is measured by monitoring the accumulation of fluorescent substrate in bacterial cells using fluorometry. IC₅₀ values are calculated from dose-response curves. The compound's ability to potentiate antibiotic activity is assessed in combination with ciprofloxacin.
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| Cell Assay |
Cellular assays for 2-naphthylboronic acid typically evaluate its antibacterial activity and efflux pump inhibition. A standard protocol involves culturing bacterial strains (e.g., S. aureus) in growth medium at 37°C. Bacteria are treated with varying concentrations of the compound alone or in combination with antibiotics. Bacterial growth is assessed by measuring optical density (OD₆₀₀) or by colony counting. Efflux pump inhibition is evaluated by measuring the accumulation of fluorescent substrates. Minimum inhibitory concentration (MIC) values are determined. The compound's ability to potentiate antibiotic activity is assessed by measuring the fractional inhibitory concentration index.
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| Animal Protocol |
In vivo animal studies for 2-naphthylboronic acid 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 efficacy as an antibiotic adjuvant in infection models. The compound's primary value lies in its use as a research tool for studying efflux pump inhibition and as a building block for organic synthesis. Specific in vivo protocols are not available in the public literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 2-naphthylboronic acid is limited, as it is primarily a research reagent. The compound has a molecular weight of 171.99 g/mol and a molecular formula of C₁₀H₉BO₂. It is a solid at room temperature and is slightly soluble in water. As a boronic acid, it may undergo oxidation and hydrolysis. The compound's naphthalene ring suggests moderate lipophilicity. Specific ADME data is not available. The compound is stored in a dry, cool place.
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| Toxicity/Toxicokinetics |
2-Naphthylboronic acid 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 or detailed toxicological profiles are available in the public domain.
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| Additional Infomation |
2-Naphthylboronic acid (2-Naphthaleneboronic acid, CAS 32316-92-0) is a biochemical reagent with the molecular formula C₁₀H₉BO₂. It is an organoboron compound used in organic synthesis and as an inhibitor of bacterial efflux pumps. The compound is classified as a research-use-only compound not intended for diagnostic or therapeutic purposes. It is available from multiple commercial suppliers in various pack sizes. No clinical trials or approved drug status exist for this compound as it is not a therapeutic agent. Its applications are limited to research and chemical synthesis.
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| Molecular Formula |
C10H9BO2
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|---|---|
| Molecular Weight |
171.99
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| Exact Mass |
172.069
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| CAS # |
32316-92-0
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| PubChem CID |
2734375
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
381.9±25.0 °C at 760 mmHg
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| Melting Point |
269-275 °C(lit.)
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| Flash Point |
184.8±23.2 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.639
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| LogP |
2.82
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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 |
1
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| Heavy Atom Count |
13
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| Complexity |
172
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])B(C1C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C2C=1[H])O[H]
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| InChi Key |
KPTRDYONBVUWPD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H9BO2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12-13H
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| Chemical Name |
naphthalen-2-ylboronic 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 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 | 5.8143 mL | 29.0715 mL | 58.1429 mL | |
| 5 mM | 1.1629 mL | 5.8143 mL | 11.6286 mL | |
| 10 mM | 0.5814 mL | 2.9071 mL | 5.8143 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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