2-Deoxy-D-Glucose

• CAS: 154-17-6
• Catalog Number: ACM154176
• Category: Inhibitors
• Molecular Weight: 164.16
• Molecular Formula: C6H12O5
• Description: 2-Deoxy-D-glucose is a glucose molecule which has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. As such, it acts to competitively inhibit the production of glucose-6-PO4 from glucose at the phosphoglucoisomerase level. In most cells, glucose hexokinase phosphorylates 2-deoxyglucose, trapping the product 2-deoxyglucose-6-phosphate intracellularly (with exception of liver and kidney); thus, labeled forms of 2-deoxyglucose serve as a good marker for tissue glucose uptake and hexokinase activity. Many cancers have elevated glucose uptake and hexokinase levels. 2-Deoxyglucose labeled with tritium or carbon-14 has been a popular ligand for laboratory research in animal models, where distribution is assessed by tissue-slicing followed by autoradiography, sometimes in tandem with either conventional or electron microscopy.2-DG is uptaken by the glucose transporters of the cell. Therefore, cells with higher glucose uptake, for example tumor cells, have also a higher uptake of 2-DG. Since 2-DG hampers cell growth, its use as a tumor therapeutic has been suggested, and in fact, 2-DG is in clinical trials A recent clinical trial showed 2-DG can be tolerated at a dose of 63mg/kg/day, however the observed cardiac side-effects (prolongation of the Q-T interval) at this dose and the fact that a majority of patients’ (66%) cancer progressed casts doubt on the feasibility of this reagent for further clinical use. However, it is not completely clear how 2-DG inhibits cell growth. The fact that glycolysis is inhibited by 2-DG, seems not to be sufficient to explain why 2-DG treated cells stop growing ; Clinicians have noted that 2-DG is metabolised in the pentose phosphate pathway in red blood cells at least, although the significance of this for other cell types and for cancer treatment in general is unclear.Work on the ketogenic diet as a treatment for epilepsy have investigated the role of glycolysis in the disease. 2-Deoxyglucose has been proposed by Garriga-Canut et al. as a mimic for the ketogenic diet, and shows great promise as a new anti-epileptic drug. The authors suggest that 2-DG works, in part, by increasing the expression of Brain-derived neurotrophic factor (BDNF), Nerve growth factor (NGF), Arc (protein) (ARC), and Basic fibroblast growth factor (FGF2). Such uses are complicated by the fact that 2-deoxyglucose does have some toxicity.By combining the sugar 2-Deoxy-D-glucose (2-DG) with fenofibrate, a compound that has been safely used in humans for more than 40 years to lower cholesterol and triglycerides, the entire tumor could effectively be targeted without the use of toxic chemotherapy.2-DG has been used as a targeted optical imaging agent for fluorescent in vivo imaging. In clinical medical imaging (PET scanning), fluorodeoxyglucose is used, where one of the 2-hydrogens of 2-deoxy-D-glucose is replaced with the positron-emitting isotope fluorine-18, which emits paired gamma rays, allowing distribution of the tracer to be imaged by external gamma camera(s). This is increasingly done in tandem with a CT function which is part of the same PET/CT machine, to allow better localization of small-volume tissue glucose-uptake differences.
• Synonyms: D-2-Glucodesose
• IUPAC Name: (3R,4S,5R)-3,4,5,6-Tetrahydroxyhexanal
• Canonical SMILES: C(C=O)C(C(C(CO)O)O)O
• InChI: InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1
• InChI Key: VRYALKFFQXWPIH-PBXRRBTRSA-N
• Boiling Point: 211.61 °C
• Melting Point: 146-147 °C(lit.)
• Flash Point: 202.3 °C
• Density: 1.1738 g/cm³
• Solubility: Soluble in water
• Appearance: White crystalline
• Storage: 2-8 °C
• Complexity: 116
• EC Number: 205-823-0
• Exact Mass: 164.06847348
• Hazard Codes: Xn
• Hazard Statements: Xn,Xi
• HS Code: 2912491000
• Isomeric SMILES: C(C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
• LogP: -2.34960
• MDL Number: MFCD00151328
• Monoisotopic Mass: 164.06847348
• pKa: 12.52 (25°C)
• PSA: 97.99
• Refractive Index: 46.5 ° (C=1, H₂O)
• Safety Description: 24/25-37/39-36-26
• Solubility In Water: Soluble
• Stability: Stable under normal temperatures and pressures.
• Storage Conditions: 0-6ºC
• Topological Polar Surface Area: 98 Ų
• Vapor Pressure: 1.8E-08mmHg at 25°C
• WGK Germany: 3

Custom Q&A

What is the molecular formula of 2-deoxyglucose?

The molecular formula of 2-deoxyglucose is C6H12O5.

What is the molecular weight of 2-deoxyglucose?

The molecular weight of 2-deoxyglucose is 164.16 g/mol.

What is 2-deoxyglucose predominantly used for in its radiolabeled form?

2-deoxyglucose is predominantly used as a diagnostic agent in its radiolabeled form to determine glucose metabolism in diseases such as cardiovascular disease, tumors, and Alzheimer's disease.

How is radiolabeled 2-deoxyglucose used in positron emission tomography (PET)?

Radiolabeled 2-deoxyglucose is used in PET to determine glucose metabolism, which is altered in diseases.

What is the potential therapeutic use of 2-deoxyglucose as an investigational drug?

2-deoxyglucose is being studied as an anticancer and antiviral agent.

How does 2-deoxyglucose work as an anticancer agent?

2-deoxyglucose acts as a glycolysis inhibitor in hypoxic cancer cells, preventing ATP production and cell survival.

What effect does 2-deoxyglucose have on herpes simplex virus?

2-deoxyglucose was shown to be effective against herpes simplex virus by affecting the virus' ability to penetrate cells.

What is the IUPAC name of 2-deoxyglucose?

The IUPAC name of 2-deoxyglucose is (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal.

What is the Canonical SMILES representation of 2-deoxyglucose?

The Canonical SMILES of 2-deoxyglucose is C(C=O)C(C(C(CO)O)O)O.

What is the InChIKey of 2-deoxyglucose?

The InChIKey of 2-deoxyglucose is VRYALKFFQXWPIH-PBXRRBTRSA-N.