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| Targets |
Cis-diols (carbohydrates, glycoproteins, glycans, sialic acid), as well as serine proteases and lipases. The primary mechanism of action involves the ability of the boronic acid moiety to form reversible covalent bonds with the cis-diol groups of carbohydrates, facilitating the detection and quantification of glycosylated compounds. The dansyl group provides a fluorescent signal that changes upon binding, enabling sensitive measurements. Additionally, the compound inhibits certain serine proteases and lipases by forming covalent bonds with serine residues in the active sites of these enzymes, allowing researchers to study enzymatic mechanisms and pathways.
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| ln Vitro |
In vitro, 3-(Dansylamino)phenylboronic acid is used as a fluorescence-based probe for the detection of glucose and other saccharides. At concentrations of 10-100 uM, it binds to sialic acid residues on cell surfaces and glycoproteins, resulting in changes in fluorescence intensity that can be correlated with the concentration of the target analyte. It has been employed in fluorometric measurement of glycosylated albumin in human serum, providing insights into diabetes management and related conditions. The compound also acts as an inhibitor for certain serine proteases and lipases, with IC50 values in the micromolar range. Its ability to form reversible covalent bonds with active-site serines allows detailed studies of enzyme kinetics and inhibition mechanisms.
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| ln Vivo |
In vivo applications of 3-(Dansylamino)phenylboronic acid are primarily explored in the context of imaging glycosylation patterns or enzyme activity in animal models. Fluorescent probes based on this compound could be used for real-time monitoring of glucose levels in diabetic animal models, although detailed in vivo efficacy data are limited. Its relatively low toxicity and reversible binding make it a candidate for in vivo diagnostic imaging. However, most of the published research focuses on in vitro or ex vivo applications, such as analyzing glycosylation of proteins in tissue extracts or labeling glycoproteins in fixed cells. Further studies are needed to validate its in vivo utility for imaging and therapeutic applications.
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| Enzyme Assay |
In a typical cell-free binding assay, 3-(Dansylamino)phenylboronic acid is dissolved in a suitable buffer (e.g., 50 mM phosphate buffered saline, pH 7.4) at a concentration of 10-50 uM. A solution containing cis-diols (e.g., D-glucose, D-fructose, sialic acid) at various concentrations (0-100 mM) is added to the probe solution. The mixture is incubated at room temperature for 10-30 minutes to allow binding equilibrium to be reached. Fluorescence intensity is measured using a fluorimeter or plate reader with excitation at 335-350 nm and emission at 520-550 nm. An increase or decrease in fluorescence upon addition of the carbohydrate indicates binding. The dissociation constant (Kd) can be calculated by fitting the fluorescence change as a function of carbohydrate concentration to a binding isotherm. For competition assays, other boronic acid derivatives or known binding inhibitors can be added to evaluate specificity.
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| Cell Assay |
A typical cell labeling protocol involves the following steps. Cells (e.g., HeLa, CHO, or primary neurons) are seeded on coverslips or in 96-well plates at 1×10⁴-5×10⁴ cells per well 24 hours prior to staining. 3-(Dansylamino)phenylboronic acid is prepared as a 10 mM stock solution in DMSO, then diluted to a working concentration of 10-100 uM in serum-free medium or HEPES buffer (pH 7.4). Cells are washed twice with PBS, then incubated with the diluted dye solution for 15-30 minutes at 37degC or room temperature. After incubation, cells are washed 3 times with PBS to remove unbound probe. If desired, cells can be fixed with 4% paraformaldehyde for 10-15 minutes at room temperature before imaging. Fluorescence imaging is performed using a fluorescence microscope or confocal microscope with excitation at 340-380 nm (UV/blue) and emission at 520-550 nm (green). For flow cytometry analysis, cells are detached with trypsin, washed with PBS, and resuspended at 1×10⁶ cells/mL for analysis on a flow cytometer equipped with a UV laser (355 nm) and a 525 nm emission filter. For live-cell imaging, cells are kept in phenol red-free medium and imaged at 37degC with 5% CO2.
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| Animal Protocol |
In vivo administration protocols for 3-(Dansylamino)phenylboronic acid are not well-documented in the literature due to its primary use as an in vitro probe. For potential in vivo imaging studies, the compound may be prepared in sterile PBS or 5% DMSO/PBS at a concentration of 1-10 mg/mL. Intravenous injection (tail vein) of 50-200 uL (dose of 1-10 mg/kg) may be administered to anesthetized mice. Animals can be imaged at various time points (0, 1, 2, 4, 8, 24 hours post-injection) using an in vivo imaging system with excitation at 350-380 nm and emission at 520-560 nm. For tissue distribution studies, mice are euthanized at predetermined time points, and organs (liver, spleen, kidney, lung, heart, brain) are harvested for fluorescence imaging and quantification. Tissue sections may be prepared for histological analysis to assess probe localization. However, it is important to note that in vivo imaging may be challenging due to the UV excitation requirement (which suffers from poor tissue penetration and high autofluorescence). Researchers are advised to use near-infrared probes for deep tissue imaging.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 3-(Dansylamino)phenylboronic acid is limited due to its status as a research chemical. Based on its low molecular weight (370.23 Da) and the presence of a dansyl group, the compound is expected to be moderately lipophilic (estimated logP ~ 1.5-2.5). After intravenous administration, the compound likely has a circulation half-life of 0.5-2 hours, with rapid distribution into tissues. The boronic acid group may interact with plasma proteins, leading to moderate protein binding (~70-90%). The compound is likely metabolized in the liver via oxidation, glucuronidation, or sulfation, with metabolites excreted in the urine and feces. The dansyl group provides fluorescence that could be used to track its distribution ex vivo. For accurate quantitative PK data, researchers are advised to perform custom studies using HPLC-MS/MS, as publicly available data is scarce.
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| Toxicity/Toxicokinetics |
Toxicological data for 3-(Dansylamino)phenylboronic acid indicates that it is for research use only and is not intended for human therapeutic use. The compound may be an irritant to the eyes, skin, and respiratory tract. Standard laboratory safety precautions, including the use of gloves, a lab coat, and eye protection, should be followed when handling the compound. Avoid inhalation of dust or contact with skin. In vitro cytotoxicity studies suggest that the compound is relatively non-toxic at concentrations up to 100 uM in cell culture, with no significant reduction in cell viability compared to controls. In vivo acute toxicity data are limited; however, compounds containing boronic acid groups are generally considered to have low acute toxicity. No long-term carcinogenicity or reproductive toxicity studies have been conducted.
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| References | |
| Additional Infomation |
3-(Dansylamino)phenylboronic acid is a research-grade fluorescent probe with no approved clinical applications. It is supplied as a solid (powder) with a purity of >98% (typically 98-99%). The compound is soluble in DMSO (10-20 mg/mL), DMF, and methanol, but has limited aqueous solubility. It should be stored at -20degC, protected from light, and in a dry environment to prevent moisture absorption. Stock solutions in DMSO can be stored at -20degC for up to 3 months. The compound is widely used for the detection and quantification of carbohydrates in solution, for labeling glycoproteins in cell lysates or on cell surfaces, and as an inhibitor in enzyme studies. Synonyms include D0520, (3-(((5-(Dimethylamino)-1-naphthyl)sulfonyl)amino)phenyl)boronic acid, and [3-[(5-Dimethylamino-1-naphthyl)sulfonylamino]phenyl]boronic acid.
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| Molecular Formula |
C18H19BN2O4S
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| Molecular Weight |
370.23046
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| Exact Mass |
370.116
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| CAS # |
75806-94-9
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| PubChem CID |
150643
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.39g/cm3
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| Boiling Point |
599.3ºC at 760 mmHg
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| Flash Point |
316.3ºC
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| Index of Refraction |
1.685
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| LogP |
2.54
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
26
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| Complexity |
566
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
TYXMKSYBCDTGDU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H19BN2O4S/c1-21(2)17-10-4-9-16-15(17)8-5-11-18(16)26(24,25)20-14-7-3-6-13(12-14)19(22)23/h3-12,20,22-23H,1-2H3
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| Chemical Name |
[3-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]phenyl]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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 2.7010 mL | 13.5051 mL | 27.0102 mL | |
| 5 mM | 0.5402 mL | 2.7010 mL | 5.4020 mL | |
| 10 mM | 0.2701 mL | 1.3505 mL | 2.7010 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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