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Deoxyglucose

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Template:Chembox OtherNamesTemplate:Chembox Density
style="background: #F8EABA; text-align: center;" colspan="2" 2-Deoxy-D-glucose[1]
2-Deoxy-D-glucose
Identifiers
CAS number 154-17-6
SMILES O[C@H](C(CO)O[C@H](O)C1)[C@H]1O
Properties
Molecular formula C6H12O5
Molar mass 164.16 g/mol
Melting point

142-144 °C

style="background: #F8EABA; text-align: center;" colspan="2" Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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. 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.

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 as tumor therapeutic has been suggested, and in fact, 2-DG is in clinical trials [2] 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 [3]

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.[4] The authors 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.

ReferencesEdit

  1. Merck Index, 11th Edition, 2886.
  2. Pelicano H, Martin DS, Xu RH, Huang P (2006) Glycolysis inhibition for anticancer treatment. Oncogene 25:4633–4646.
  3. M Ralser, MM Wamelink, EA Struys, C Joppich, S Krobitsch, C Jakobs, H Lehrach Proc Natl Acad Sci U S A, 2008, DOI:10.1073/pnas.0803090105
  4. 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", Nat Neurosci, 9, 1382 - 1387 (2006). DOI:10.1038/nn1791

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