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2-Deoxy-D-glucose

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					2-Deoxy-D-glucose
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2-Deoxy- D-glucose is a glucose molecule which has the 2-hydroxyl group
                                                                                                         2-Deoxy-D-glucose[1]
replaced by hydrogen, so that it cannot undergo further glycolysis. Glucose
hexokinase traps this substance in most cells (with exception of liver and
kidney)[citation needed] 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.
                                                                                                                  IUPAC name
2-DG is uptaken by the glucose transporters of the cell. Therefore, cells with
                                                                                               (4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol
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                                       Other names

suggested, and in fact, 2-DG is in clinical trials [2] However, it is not completely                             2-Deoxyglucose
clear how 2-DG inhibits cell growth. The fact that glycolysis is inhibited by 2-DG,                            2-Deoxy- D -mannose
                                                                                                         2-Deoxy- D -arabino-hexose
seems not to be sufficient to explain why 2-DG treated cells stop growing [3]
                                                                                                                      2-DG
Work on the ketogenic diet as a treatment for epilepsy have investigated the role
                                                                                                                     Identifiers
of glycolysis in the disease. 2-Deoxyglucose has been proposed by Garriga-
                                                                                               CAS number                   154-17-6
Canut et al. as a mimic for the ketogenic diet, and shows great promise as a new
                                                                                               ChemSpider                   388402
anti-epileptic drug.[4] The authors suggest that 2-DG works, in part, by
                                                                                               UNII                         9G2MP84A8W
decreasing the expression of Brain-derived neurotrophic factor (BDNF). Such
                                                                                               Jmol-3D images              Image 1
uses are complicated by the fact that 2-deoxyglucose does have some toxicity.
                                                                                                                      SMILES
2-DG has been used as a targeted optical imaging agent for fluorescent in vivo                 O[C@H](C(CO)O[C@H](O)C1)[C@H]1O
imaging. [5][6] In clinical medical imaging (PET scanning), fluorodeoxyglucose is
                                                                                                                       InChI
used, where one of the 2-hydrogens of 2-deoxy-D-glucose is replaced with the
                                                                                               InChI=1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-
positron-emitting isotope fluorine-18, which emits paired gamma rays, allowing                 4/h3-10H,1-2H2/t3-,4-,5?,6+/m1/s1
distribution of the tracer to be imaged by external gamma camera(s). This is                   Key: PMMURAAUARKVCB-CERMHHMHSA-N
increasingly done in tandem with a CT function which is part of the same PET/CT
                                                                                                                    Properties
machine, to allow better localization of small-volume tissue glucose-uptake
                                                                                               Molecular formula            C6 H12 O 5
differences.
                                                                                               Molar mass                   164.16 g/mol
                                                                                               Melting point                142–144 °C
References
                                                                                                                (verify) (what is:   / ?)
   1. ^ Merck Index, 11th Edition, 2886.                                                Except where noted otherwise, data are given for
   2. ^ Pelicano, H; Martin, DS; Xu, RH; Huang, P (2006). "Glycolysis inhibition for        materials in their standard state (at 25 °C,
      anticancer treatment". Oncogene 25 (34): 4633–4646.                                                     100 kPa)
      doi:10.1038/sj.onc.1209597 . PMID 16892078 .                                                      Infobox references
   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
      Garriga-Canut, M.; Schoenike, B.; Qazi, R.; Bergendahl, K.; Daley, T. J.; Pfender, R. M.; Morrison, J. F.; Ockuly, J. et al. (2006). "2-
      Deoxy-D-glucose reduces epilepsy progression by NRSF-CtBP–dependent metabolic regulation of chromatin structure". Nature
      Neuroscience 9 (11): 1382–1387. doi:10.1038/nn1791 . PMID 17041593 . edit
   5. ^ Kovar, J., Volcheck, W., Sevick-Muraca, E., Simpson, M.A., and Olive, D.M., Analytical Biochemistry, Vol. 384 (2009) 254-262
      Download PDF
   6. ^ Cheng, Z., Levi, J., Xiong, Z., Gheysens, O., Keren, S., Chen, X., and Gambhir, S., Bioconjugate Chemistry, 17(3), (2006), 662-
    669



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