2-Deoxy-D-glucose

Chembox new
Name = 2-Deoxy-D-glucose
Reference = ["Merck Index", 11th Edition, 2886.]
ImageFile = 2-Deoxy-D-glucose.png ImageName = 2-Deoxy-D-glucose
IUPACName = 2-Deoxy-D-glucose
OtherNames = 2-Deoxyglucose
2-Deoxy-D-mannose
2-Deoxy-D-arabino-hexose
2-DG
Section1 = Chembox Identifiers
CASNo = 154-17-6
SMILES = O [C@H] (C(CO)O [C@H] (O)C1) [C@H] 1O
Section2 = Chembox Properties
Formula = C₆H₁₂O₅
MolarMass = 164.16 g/mol
Density = ? g/cm³
MeltingPt = 142-144 °C

2-Deoxy-D-glucose is a glucose molecule which has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. Glucose hexokinase traps this substance in most cells (with exception of liver and kidney) so that it makes a good marker for tissue glucose use 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.

Recent 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. [Mireia Garriga-Canut, Barry Schoenike, Romena Qazi, Karen Bergendahl, Timothy J Daley, Rebecca M Pfender, John F Morrison, Jeffrey Ockuly, Carl Stafstrom, Thomas Sutula & Avtar Roopra, "2-Deoxy-D-glucose reduces epilepsy progression by NRSF-CtBP–dependent metabolic regulation of chromatin structure", "Nature Neuroscience", 9, 1382 - 1387 (2006). doi|10.1038/nn1791] Garriga-Canut et al suggest that 2-DG works, in part, by decreasing the expression of Brain-derived neurotrophic factor (BDNF). Such uses are complicated by the fact that 2-deoxyglucose does have some toxicity.

In living systems, such as in 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.

References