2-Deoxy-2-fluoro-L-fucose is an L-fucose analogue and a fucosylation inhibitor. 2-Deoxy-2-fluoro-L-fucose inhibits de novo synthesis of GDP-fucose in mammalian cells. Fucosylation is a relatively well-established biomarker of progression in many human cancers, e.g., pancreatic cancer and hepatocellular carcinoma.

Physicochemical Properties

Molecular Formula	C6H11FO4
Molecular Weight	166.15
Exact Mass	166.064
CAS #	70763-62-1
PubChem CID	125766
Appearance	White to off-white solid powder
Density	1.335g/cm3
Boiling Point	386.5ºC at 760 mmHg
Flash Point	187.6ºC
Index of Refraction	1.469
LogP	-1.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Heavy Atom Count	11
Complexity	130
Defined Atom Stereocenter Count	4
InChi Key	SQTFKIKSQNCWGJ-UHFFFAOYSA-N
InChi Code	InChI=1S/C6H11FO4/c1-3(9)5(10)6(11)4(7)2-8/h2-6,9-11H,1H3
Chemical Name	2-fluoro-3,4,5-trihydroxyhexanal
HS Tariff Code	2934.99.9001
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)

Biological Activity

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].
References	[1]. Core-Fucosylated Tetra-Antennary N-Glycan Containing A Single N-Acetyllactosamine Branch Is Associated with Poor Survival Outcome in Breast Cancer. Int J Mol Sci. 2019;20(10):2528. Published 2019 May 23.
Additional Infomation	2-fluorofucose is under investigation in clinical trial NCT02952989 (A Safety Study of SGN-2FF for Patients With Advanced Solid Tumors). 2-Fluorofucose is an orally bioavailable fluorinated analog of fucose that is a protein fucosylation inhibitor, with potential antineoplastic and immunomodulating activities. Upon administration, 2-fluorofucose (2-FF) mimics fucose and is converted to guanosine diphosphate (GDP)-2FF, which prevents the formation of the fucosylation substrate GDP-fucose, and the incorporation of fucose into glycoproteins by fucosyltransferase. As fucosylation of glycoproteins plays a key role in many biological processes, such as protein function, receptor binding, cell signaling and cellular adhesion, and is essential for tumor progression, blocking fucosylation decreases tumor cell growth. In addition, blocking fucosylation of monoclonal antibodies generates fucose-deficient antibodies that exert enhanced antibody-dependent cell-mediated cytotoxicity (ADCC).

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (601.87 mM)

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. 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. 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 corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

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.