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| 5mg |
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| 10mg |
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| Targets |
Fucosyltransferases, through the inhibition of GDP-fucose biosynthesis. 2-Deoxy-2-fluoro-L-fucose is a substrate-based inhibitor of fucosyltransferases. It is metabolized inside the cell to GDP-2-deoxy-2-fluoro-L-fucose, which acts as a competitive inhibitor of fucosyltransferases, such as α1,3-fucosyltransferase V, with a Ki of 4.2 µM. By inhibiting these enzymes, it blocks the transfer of fucose to glycoproteins and glycolipids, thereby reducing protein fucosylation.
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| ln Vitro |
2-Deoxy-2-fluoro-L-fucose (2FF) (100–500 μM) inhibits the growth of fucosylation in 4T1 cells[1]. Phosphorylation of Smad 1/5 and Smad 2 is reduced by 2-Deoxy-2-fluoro-L-fucose (100 μM; 4T1 cells)[1].
In vitro, 2-Deoxy-2-fluoro-L-fucose has been shown to inhibit protein fucosylation. It can be converted to GDP-2-deoxy-2-fluoro-L-fucose, which acts as a competitive inhibitor of fucosyltransferases. Its activity is measured by its ability to reduce the incorporation of fucose into glycoproteins, as detected by lectin blotting or mass spectrometry. |
| ln Vivo |
In vivo, 2-Deoxy-2-fluoro-L-fucose is used as a tool to study the role of fucosylation in various biological processes. By inhibiting fucosylation, it can modulate immune responses and tumor growth. It is being investigated for its potential to increase the therapeutic efficacy of antibodies by reducing their fucosylation, which enhances antibody-dependent cellular cytotoxicity (ADCC).
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| Enzyme Assay |
The inhibitory activity of 2-Deoxy-2-fluoro-L-fucose can be assessed in a cell-free fucosyltransferase assay. The enzyme is incubated with its substrate, GDP-fucose, and an acceptor molecule in the presence of varying concentrations of the inhibitor. The transfer of fucose is measured, and the Ki is determined.
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| Cell Assay |
To study its cellular effects, cells are treated with 2-Deoxy-2-fluoro-L-fucose. The level of protein fucosylation is assessed by lectin blotting using fucose-specific lectins, such as Aleuria aurantia lectin (AAL). The effect on cell signaling, adhesion, or immune function can be measured using standard assays.
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| Animal Protocol |
The in vivo activity of 2-Deoxy-2-fluoro-L-fucose can be studied in mouse models of cancer or immune-related diseases. The compound is administered orally or intraperitoneally. The effect on protein fucosylation in tissues, tumor growth, or immune cell function is assessed.
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| ADME/Pharmacokinetics |
2-Deoxy-2-fluoro-L-fucose has a molecular weight of 166.15 g/mol. It is a monosaccharide analog. It is soluble in water and other polar solvents. It is typically stored at -20°C to maintain stability. Specific pharmacokinetic data are not widely published.
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| Toxicity/Toxicokinetics |
Toxicological data for 2-Deoxy-2-fluoro-L-fucose are not detailed, as it is a research compound. It is not intended for human or veterinary use. Standard laboratory safety precautions should be followed when handling the compound.
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| References | |
| Additional Infomation |
2-Fluorofucose is being investigated in the clinical trial NCT02952989 (Safety Study of SGN-2FF in Patients with Advanced Solid Tumors). 2-Fluorofucose is an orally bioavailable fluorinated fucose analogue and a protein fucosylation inhibitor with potential antitumor and immunomodulatory activities. After administration, 2-fluorofucose (2-FF) mimics fucose and is converted to guanosine diphosphate (GDP)-2FF, thereby preventing the formation of the fucosylation substrate GDP-fucose and inhibiting the incorporation of fucose into glycoproteins via fucosyltransferases. Since glycoprotein fucosylation plays a crucial role in many biological processes, such as protein function, receptor binding, cell signaling, and cell adhesion, and is essential for tumor progression, blocking fucosylation can reduce tumor cell growth. Furthermore, blocking the fucosylation of monoclonal antibodies produces fucose-deficient antibodies, thereby enhancing antibody-dependent cell-mediated cytotoxicity (ADCC).
2-Deoxy-2-fluoro-L-fucose is a research tool used extensively in glycobiology to study the role of fucosylation in various biological processes. It is a chemically modified sugar that inhibits protein fucosylation, making it valuable for investigating carbohydrate-mediated interactions such as cell signaling and bacterial infection processes. It is also being explored for its potential to enhance the efficacy of therapeutic antibodies and as an antineoplastic agent. It is not an approved drug. |
| Molecular Formula |
C6H11FO4
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|---|---|
| Molecular Weight |
166.15
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| Exact Mass |
166.064
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| CAS # |
70763-62-1
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| PubChem CID |
125766
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| Appearance |
White to off-white solid powder
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| Density |
1.335g/cm3
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| Boiling Point |
386.5ºC at 760 mmHg
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| Flash Point |
187.6ºC
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| Index of Refraction |
1.469
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| LogP |
-1.4
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
11
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| Complexity |
130
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C[C@@H]([C@H]([C@H]([C@@H](C=O)F)O)O)O
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| InChi Key |
SQTFKIKSQNCWGJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H11FO4/c1-3(9)5(10)6(11)4(7)2-8/h2-6,9-11H,1H3
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| Chemical Name |
2-fluoro-3,4,5-trihydroxyhexanal
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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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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: 100 mg/mL (601.87 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.05 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 25.0 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: ≥ 2.5 mg/mL (15.05 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (15.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0187 mL | 30.0933 mL | 60.1866 mL | |
| 5 mM | 1.2037 mL | 6.0187 mL | 12.0373 mL | |
| 10 mM | 0.6019 mL | 3.0093 mL | 6.0187 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.
Link: https://clinicaltrials.gov/ct2/show/NCT02952989
Conditions:Carcinoma, Non-Small-Cell Lung|Carcinoma, Renal Cell|Breast Neoplasms|Urinary Bladder Neoplasm|Carcinoma, Squamous Cell of Head and Neck|Colorectal Neoplasms|Gastric Adenocarcinoma|Gastroesophageal Junction AdenocarcinomaProducts are for research use only; We do not sell to patients
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