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| 5mg |
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| Targets |
The target of ABD-F is thiol groups (-SH) in biological molecules, including cysteine residues in proteins and small molecule thiols like glutathione. Its mechanism of action is a nucleophilic aromatic substitution reaction: the fluorine atom on the benzoxadiazole ring is displaced by the thiolate anion (-S⁻) of the target thiol under mildly basic conditions. This reaction results in the formation of a stable thioether conjugate with the benzoxadiazole fluorophore. The reaction converts the non-fluorescent or weakly fluorescent reagent into a highly fluorescent product, enabling sensitive detection of thiols.
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| ln Vitro |
In vitro, ABD-F is used as a fluorescent reagent for the detection and quantification of thiols. Its low fluorescence background and good fluorophore stability make it an excellent choice for thiol detection assays. Compared to other thiol-reactive reagents such as NBD chloride or NBD fluoride, ABD-F offers the advantage of producing stable thiol conjugates with superior fluorescence properties. The compound is used in various biochemical applications, including the determination of thiol groups in proteins, the measurement of glutathione levels in cells, and the analysis of redox status.
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| ln Vivo |
In vivo activity of ABD-F is not typically studied, as it is a fluorescent reagent for thiol detection in vitro. However, thiol-reactive probes can be used to label and track thiol-containing biomolecules in living cells or organisms. ABD-F could potentially be used to label cysteine-containing proteins or to monitor changes in thiol redox status in vivo. Its cell permeability and reactivity with intracellular thiols would determine its utility for such applications, but specific in vivo data is not available.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cell) assays using ABD-F typically involve the detection and quantification of thiols. A standard protocol for thiol determination: a sample containing thiols (e.g., protein solution or cell lysate) is incubated with ABD-F in a buffer at a specific pH (e.g., pH 8.0) for a defined period (e.g., 30-60 minutes) at room temperature or 37°C. The reaction is stopped by the addition of an acid, and the fluorescence of the resulting solution is measured using a fluorometer with excitation at 385 nm and emission at 515 nm. The thiol concentration is determined by comparing the fluorescence to a standard curve prepared with a known thiol compound, such as cysteine or glutathione.
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| Cell Assay |
In vitro cell-based assays using ABD-F would involve labeling intracellular thiols. A standard protocol: cells are cultured in a suitable medium and treated with ABD-F (e.g., 10-100 µM) for a period of time (e.g., 30-60 minutes) at 37°C. Cells are then washed with PBS to remove unreacted dye. The labeled cells can be analyzed by flow cytometry to measure the fluorescence intensity, which reflects the cellular thiol content. Alternatively, cells can be lysed, and the lysate can be analyzed by fluorescence spectroscopy or HPLC to quantify labeled thiols. This assay can be used to study changes in cellular redox status in response to oxidative stress or drug treatment.
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| Animal Protocol |
In vivo animal experiments for ABD-F are not well-documented. For thiol-reactive probes, a potential application is the imaging of thiols in living animals. A standard protocol: ABD-F or a similar thiol-reactive probe is administered intravenously or intraperitoneally to mice. After a period for distribution and reaction (e.g., 1-2 hours), animals are euthanized, and tissues are collected. Tissue sections are prepared and analyzed under a fluorescence microscope to visualize the distribution of labeled thiols. Alternatively, tissues can be homogenized, and the fluorescence can be quantified. Such studies would provide information on the thiol content and redox status of different tissues.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of ABD-F are not well-characterized. As a small molecule (MW 217.18 g/mol), it is likely to be cell-permeable. Its reactivity with thiols means that once it enters cells, it will rapidly react with intracellular thiols, forming stable conjugates. The compound is typically stored at room temperature or refrigerated, protected from light. Its solubility in aqueous buffers and organic solvents facilitates its use in various assays. The compound's stability and low fluorescence background are key advantages for its application as a thiol detection reagent.
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| Toxicity/Toxicokinetics |
Toxicity data for ABD-F is limited. As a fluorogenic reagent, it is generally handled with standard laboratory precautions. The compound contains a fluorine atom and a sulfonamide group, which may pose some toxicity concerns. However, at the concentrations typically used for thiol detection assays (micromolar to low millimolar), it is not expected to be highly toxic. Nevertheless, inhalation, ingestion, and skin contact should be avoided. Appropriate personal protective equipment should be worn when handling the compound.
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| References | |
| Additional Infomation |
ABD-F is a sensitive and specific fluorescent reagent for the detection of thiols. Its benzoxadiazole core reacts with thiol groups to form stable fluorescent conjugates. The compound has low fluorescence background and good fluorophore stability. It is used for the detection and quantification of thiol groups in proteins and small molecules. ABD-F is not a drug and has no clinical use or approval status. It is commercially available from chemical suppliers for research purposes only.
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| Molecular Formula |
C6H4FN3O3S
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|---|---|
| Molecular Weight |
217.1777
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| Exact Mass |
216.995
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| CAS # |
91366-65-3
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| PubChem CID |
122067
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| Appearance |
Yellow to green solid powder
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
408.8±55.0 °C at 760 mmHg
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| Melting Point |
145-146ºC
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| Flash Point |
201.0±31.5 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.632
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| LogP |
0.11
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
14
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| Complexity |
317
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
XROXHZMRDABMHS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H4FN3O3S/c7-3-1-2-4(14(8,11)12)6-5(3)9-13-10-6/h1-2H,(H2,8,11,12)
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| Chemical Name |
7-fluoro-2,1,3-benzoxadiazole-4-sulfonamide
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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) |
DMSO : ~125 mg/mL (~575.56 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (9.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.6045 mL | 23.0224 mL | 46.0448 mL | |
| 5 mM | 0.9209 mL | 4.6045 mL | 9.2090 mL | |
| 10 mM | 0.4604 mL | 2.3022 mL | 4.6045 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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