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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/03 16:42:44」(JST)

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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.^[2] In most cells, glucose hexokinase phosphorylates 2-deoxyglucose, trapping the product 2-deoxyglucose-6-phosphate intracellularly (with exception of liver and kidney)^{[citation needed]}; 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 ^[3] 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.^[4] 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 ^[5]

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.^[6]

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.^[7] The authors suggest that 2-DG works, in part, by increasing the expression of Brain-derived neurotrophic factor (BDNF), Nerve growth factor (NGF), Arc (protein) (ARC), and Basic fibroblast growth factor (FGF2).^[8] Such uses are complicated by the fact that 2-deoxyglucose does have some toxicity.

2-DG has been used as a targeted optical imaging agent for fluorescent in vivo imaging.^[9]^[10] In clinical 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[edit]

^ Merck Index, 11th Edition, 2886.
^ Wick, AN; Drury, DR; Nakada, HI; Wolfe, JB (1957). "Localization of the primary metabolic block produced by 2-deoxyglucose". J Biol Chem 224 (2): 963–969. PMID 13405925.
^ Pelicano, H; Martin, DS; Xu, RH; Huang, P (2006). "Glycolysis inhibition for anticancer treatment". Oncogene 25 (34): 4633–4646. doi:10.1038/sj.onc.1209597. PMID 16892078.
^ http://www.ncbi.nlm.nih.gov/pubmed/23228990
^ 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
^ JD O'Dea
^ 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.; Stafstrom, C.; Sutula, T.; Roopra, A. (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
^ Jia Yao, Shuhua Chen, Zisu Mao, Enrique Cadenas, Roberta Diaz Brinton "2-Deoxy-D-Glucose Treatment Induces Ketogenesis, Sustains Mitochondrial Function, and Reduces Pathology in Female Mouse Model of Alzheimer's Disease", PLOS ONE
^ Kovar, J., Volcheck, W., Sevick-Muraca, E., Simpson, M.A., and Olive, D.M., Analytical Biochemistry, Vol. 384 (2009) 254-262 Download PDF
^ 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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English Journal

Apoptosis, necrosis and autophagy are influenced by metabolic energy sources in cultured rat spermatocytes.

Bustamante-Marín X, Quiroga C, Lavandero S, Reyes JG, Moreno RD.SourceDepartamento de Fisiología, Facultad de Ciencias Biológicas, Pontificia Universidad Católica de Chile, Alameda 340, Santiago, Chile.
Apoptosis : an international journal on programmed cell death.Apoptosis.2012 Jun;17(6):539-50.
Apoptosis, necrosis and autophagy are mechanistically related processes that control tissue homeostasis and cell survival. In the testis, germ cell death is important for controlling sperm output, but it is unknown whether or not germ cells can switch from apoptosis to necrosis, as has been reported
PMID 22484449

Mass screening of emergency department visitors for occult radionuclide contamination.

Huang YC, Tu DG.SourceDepartments of aEmergency Medicine bNuclear Medicine, Chiayi Christian Hospital, Chiayi City cDepartment of Life Science, National Chung Cheng University, Chia-Yi dCollege of Health Sciences, Chang Jung Christian University, Tainan, Taiwan.
European journal of emergency medicine : official journal of the European Society for Emergency Medicine.Eur J Emerg Med.2012 Jun;19(3):171-6.
OBJECTIVE: To design an effective, efficient, and affordable radiation surveillance system to screen every emergency department (ED) visitor before they enter the ED.METHODS: We chose fluoro-2-deoxyglucose as the source of γ-rays. We collected all available radiation dosimeters in the hospital, des
PMID 21857229

Japanese Journal

Effects of insulin and amyloid β_<1-42> oligomers on glucose incorporation and mitochondrial function in cultured rat hippocampal neurons

MIICHI Yoshiaki,SAKURAI Takashi,AKISAKI Taichi,YOKONO Koichi
Geriatrics & gerontology international 11(4), 517-524, 2011-10-01
NAID 10030468753

Identification and application of a different glucose uptake system that functions as an alternative to the phosphotransferase system in Corynebacterium glutamicum

Ikeda Masato,Mizuno Yuta,Awane Shin-ichi,Hayashi Masahiro,Mitsuhashi Satoshi,Takeno Seiki
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY 90(4), 1443-1451, 2011-05
… The suppressor strain SPH2, unlike the wild-type strain, exhibited a phenotype of resistance to 2-deoxyglucose which is known to be a toxic substrate for the glucose-PTS of this microbe, suggesting that strain SPH2 utilizes glucose via a different system involving a permease and native glucokinases. …
NAID 80021962923

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★リンクテーブル★

リンク元	「2-デオキシグルコース」
関連記事	「deoxyglucose」

「2-デオキシグルコース」

2-Deoxy-D-glucose
	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
CAS number	154-17-6
ChemSpider	388402
UNII	9G2MP84A8W
Jmol-3D images	Image 1
	SMILES O[C@H](C(CO)O[C@H](O)C1)[C@H]1O ;
	InChI InChI=1S/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6+/m1/s1 ; Key: PMMURAAUARKVCB-CERMHHMHSA-N ;
Properties
Molecular formula	C6H12O5
Molar mass	164.16 g/mol
Melting point	142–144 °C
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: 2-deoxyglucose 2-DG
同: 2-deoxy-D-arabino-hexose
関: グルコース、FDG、PET

グルコースの類似物質で、グルコースと同様に細胞内に取り込まれる。

「deoxyglucose」

　　[★]

デオキシグルコース

[1] Merck Index, 11th Edition, 2886.

[2] Wick, AN; Drury, DR; Nakada, HI; Wolfe, JB (1957). "Localization of the primary metabolic block produced by 2-deoxyglucose". J Biol Chem 224 (2): 963–969. PMID 13405925.

[3] Pelicano, H; Martin, DS; Xu, RH; Huang, P (2006). "Glycolysis inhibition for anticancer treatment". Oncogene 25 (34): 4633–4646. doi:10.1038/sj.onc.1209597. PMID 16892078.

[4] ttp://www.ncbi.nlm.nih.gov/pubmed/23228990

[5] 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

[6] JD O'Dea

[7] 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.; Stafstrom, C.; Sutula, T.; Roopra, A. (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

[8] Jia Yao, Shuhua Chen, Zisu Mao, Enrique Cadenas, Roberta Diaz Brinton "2-Deoxy-D-Glucose Treatment Induces Ketogenesis, Sustains Mitochondrial Function, and Reduces Pathology in Female Mouse Model of Alzheimer's Disease", PLOS ONE

[9] Kovar, J., Volcheck, W., Sevick-Muraca, E., Simpson, M.A., and Olive, D.M., Analytical Biochemistry, Vol. 384 (2009) 254-262 Download PDF

[10] 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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2-deoxyglucose