2-Deoxy-D-glucose
 |
|
| Names | |
|---|---|
|
IUPAC name
(4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol
|
|
| Other names
2-Deoxyglucose
2-Deoxy-D-mannose 2-Deoxy-D-arabino-hexose 2-DG |
|
| Identifiers | |
|
3D model (Jmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.005.295 |
| UNII | |
|
|
|
|
| Properties | |
| C6H12O5 | |
| Molar mass | 164.16 g/mol |
| Melting point | 142 to 144 °C (288 to 291 °F; 415 to 417 K) |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
 (what is   ?) |
|
| Infobox references | |
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 63 mg/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 reducing 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.
...
Wikipedia