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2-deoxy-D-glucose

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2-Deoxy-D-glucose[1]
2-Deoxy-D-glucose
Chemical name 2-Deoxy-D-glucose
Other names 2-Deoxyglucose
2-Deoxy-D-mannose
2-Deoxy-D-arabino-hexose
2-DG
Chemical formula C6H12O5
Molecular mass 164.16 g/mol
CAS number [154-17-6]
Density  ? g/cm3
Melting point 142-144 °C
SMILES O[C@H](C(CO)O[C@H](O)C1)[C@H]1O
Disclaimer and references

2-Deoxy-D-glucose is a 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.[2] Such uses are complicated by the fact that 2-deoxyglucose does have some toxicity, since it interfers with glucose metabolism in tissues which normally run almost exclusively on glucose, notably the brain.

In living systems, such as in medical imaging (PET scaning), 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.

ReferencesEdit

  1. Merck Index, 11th Edition, 2886.
  2. 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

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