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2-Deoxy-2-fluoro-D-mannose

2-Deoxy-2-fluoro-D-mannose is an antiviral mannose analog that inhibits the formation of oligosaccharide chains during protein glycosylation.
2-Deoxy-2-fluoro-D-mannose
2-Deoxy-2-fluoro-D-mannose Chemical Structure CAS No.: 38440-79-8
Product category: Virus Protease
This product is for research use only, not for human use. We do not sell to patients.
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10mg
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Product Description
2-Deoxy-2-fluoro-D-mannose is an antiviral mannose analog that inhibits the formation of oligosaccharide chains during protein glycosylation.
2-Deoxy-2-fluoro-D-mannose (2-FM; CAS# 38440-79-8; C6H11FO5; MW 182.15) is a fluorinated sugar analog of mannose. It is a critical precursor for the synthesis of the radiotracer 2-deoxy-2-[¹⁸F]fluoro-D-mannose ([¹⁸F]FDM). FDM is a positron emission tomography (PET) imaging agent. The non-radioactive form is used as a reference standard and a chemical intermediate. It is also a potential anti-cancer and anti-inflammatory agent.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Deoxy-2-fluoro-D-mannose (2-FM) is a glucose analog. It is transported into cells by glucose transporters (GLUTs), primarily GLUT1. Once inside the cell, it is phosphorylated by hexokinase to 2-deoxy-2-fluoro-D-mannose-6-phosphate (FDM-6-P). Unlike 2-deoxy-2-fluoro-D-glucose (FDG), FDM is not a substrate for glucose-6-phosphate isomerase, so it does not enter the glycolysis pathway. Instead, it is further metabolized to a mannose derivative, which may affect protein glycosylation. The mannose analog is a substrate for hexokinase.
ln Vitro
2-Deoxy-2-fluoro-D-mannose has demonstrated cytotoxic effects comparable to 2-DG. It is a known inducer of type II cell death (autophagy) in glioma cell lines (U87). The IC₅0 for U87 cells is in the low millimolar range (1-10 mM). It inhibits the growth of cancer cells by interfering with glucose metabolism and protein glycosylation. It has lower uptake in the brain and faster clearance from the bloodstream compared to FDG, making it a promising PET tracer for brain tumors. It also reduces atherosclerosis.
ln Vivo
2-Deoxy-2-fluoro-D-mannose is not used as a drug. The radiofluorinated form ([¹⁸F]FDM) is used as a PET imaging agent to detect tumors and sites of inflammation. It has shown comparable tumor uptake to the standard tracer [¹⁸F]FDG but with the advantage of lower brain uptake. It is also used to image bacterial infections. In research, the non-radioactive form can be administered to animals to study mannose metabolism. It has been shown to reduce atherosclerotic plaque inflammation in mouse models.
Enzyme Assay
[¹⁸F]FDM is a PET tracer. The purity of the radiotracer is determined by radio-HPLC and radio-TLC. For the non-radioactive standard, in vitro hexokinase activity assays are performed. Human hexokinase II (HK-II) is incubated with 0.5 mM ATP, 10 mM MgCl2, and varying concentrations of 2-Deoxy-2-fluoro-D-mannose (0-10 mM) in 50 mM Tris-HCl buffer (pH 7.5) at 37degC for 30 min. The formation of the product (FDM-6-P) is measured by a coupled enzyme assay using G6PDH. The Km (Michaelis constant) is calculated.
Cell Assay
For the evaluation of cell viability, U87 glioma cells are seeded in 96-well plates (1×10⁴ cells/well) and treated with 2-Deoxy-2-fluoro-D-mannose (0-20 mM) for 48 h. Cell viability is measured by MTT assay. For metabolic studies, cells are treated with 2-10 mM of the compound for 24 h. The accumulation of the phosphorylated form is measured by LC-MS/MS. For GLUT1 transport assays, 3H-labeled 2-deoxy-2-fluoro-D-mannose is incubated with GLUT1-overexpressing HEK293 cells, and the uptake is measured.
Animal Protocol
In vivo PET imaging: Male Balb/c mice bearing subcutaneous U87 human glioma xenografts (tumor size 5-10 mm) are injected intravenously with 2-10 mCi of [¹⁸F]FDM. A static PET scan is acquired at 60 min post-injection. The standardized uptake value (SUV) of the tumor is calculated and compared to the contralateral background. For toxicology studies, C57BL/6 mice are injected with 0.1-1 mg/kg of 2-Deoxy-2-fluoro-D-mannose (non-radioactive) intravenously. Blood glucose levels are measured at 0, 15, 30, 60, 120 min. No significant hypoglycemia is observed. The compound is non-toxic at the doses used for imaging.
ADME/Pharmacokinetics
2-Deoxy-2-fluoro-D-mannose (MW 182.15, Log P -1.8) is highly hydrophilic. After intravenous injection, [¹⁸F]FDM distributes rapidly to the liver, kidneys, and tumors. It is cleared from the bloodstream faster than FDG. The radiotracer is not metabolized beyond the 6-phosphate form and is trapped in the cell. The non-radioactive compound is not used pharmacologically. The estimated elimination half-life is < 60 minutes in mice. The radiolabeled compound is for diagnostic PET imaging.
Toxicity/Toxicokinetics
For 2-Deoxy-2-fluoro-D-mannose, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). The radioactive form is subject to radiation safety regulations. Storage: at 2-8degC, dry.
References

[1]. McDowell W, Datema R, Romero PA, Schwarz RT. Mechanism of inhibition of protein glycosylation by the antiviral sugar analogue 2-deoxy-2-fluoro-D-mannose: inhibition of synthesis of man(GlcNAc)2-PP-Dol by the guanosine diphosphate ester. Biochemistry. 1985;24(27):8145-8152.

Additional Infomation
2-Deoxy-2-fluoro-D-mannose (2-FM; CAS# 38440-79-8) is a research-grade fluorinated sugar analog. It is not an FDA-approved drug. It is used as a precursor for the PET tracer [¹⁸F]FDM for tumor imaging and as a reference standard in metabolic research. For research use only, not for diagnostic or therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H11FO5
Molecular Weight
182.15
CAS #
38440-79-8
Appearance
Typically exists as solids at room temperature
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

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.4900 mL 27.4499 mL 54.8998 mL
5 mM 1.0980 mL 5.4900 mL 10.9800 mL
10 mM 0.5490 mL 2.7450 mL 5.4900 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.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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