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the 4th letter of the Roman alphabet (同)d

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deuteriumの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/20 03:49:06」(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

^ Merck Index, 11th Edition, 2886.
^ Wick, AN; Drury, DR; Nakada, HI; Wolfe, JB (1957). "Localization of the primary metabolic block produced by 2-deoxyglucose" (PDF). 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

Ouabain Targets the Unfolded Protein Response for Selective Killing of HepG2 Cells During Glucose Deprivation.

Ozdemir T, Nar R, Kilinc V, Alacam H, Salis O, Duzgun A, Gulten S, Bedir A.Source1 Gazi State Hospital , Samsun, Turkey .
Cancer biotherapy & radiopharmaceuticals.Cancer Biother Radiopharm.2012 Jul 3. [Epub ahead of print]
Abstract Ouabain is a cardiotonic steroid and specific inhibitor of the Na(+)/K(+)-ATPase. The relationship between ouabain treatment and the unfolded protein response (UPR) in cells is not precisely understood. Therefore, we studied the possible effects of ouabain on proliferation, apoptosis, and
PMID 22757644

Optical imaging of oral squamous cell carcinoma and cervical lymph node metastasis.

Keereweer S, Kerrebijn JD, Mol IM, Mieog JS, Van Driel PB, Baatenburg de Jong RJ, Vahrmeijer AL, Löwik CW.SourceErasmus Medical Center, Department of Otorhinolaryngology Head and Neck Surgery, Rotterdam, The Netherlands; Leiden University Medical Center, Molecular Endocrinology and Molecular Imaging, Leiden, The Netherlands. s.keereweer@erasmusmc.nl.
Head & neck.Head Neck.2012 Jul;34(7):1002-8. doi: 10.1002/hed.21861. Epub 2011 Oct 10.
BACKGROUND: In oral cancer surgery, intraoperative optical imaging could help the surgeon to determine adequate tumor-free margins.METHODS: Tumor-specific near-infrared fluorescence agents targeting epidermal growth factor receptor (CW800 EGF) or glucose transporter system (CW800 2-DG) were administ
PMID 21987435

Japanese Journal

Phosphoenolpyruvic Acid, an Intermediate of Glycolysis, Attenuates Cellular Injury Induced by Hydrogen Peroxide and 2-Deoxy-D-glucose in the Porcine Proximal Kidney Tubular Cell Line, LLC-PK1

Kondo Yuki,Ishitsuka Yoichi,Kadowaki Daisuke,Nagatome Minako,Saisho Yusuke,Kuroda Masataka,Hirata Sumio,Irikura Mitsuru,Hamasaki Naotaka,Irie Tetsumi
JOURNAL OF HEALTH SCIENCE 56(6), 727-732, 2010
… PEP (0.5-10 mM) attenuated hydrogen peroxide (H2O2)-induced cellular injury in the porcine proximal kidney tubular cell line, LLC-PK1 in a dose-dependent manner. … PEP also prevented cellular injury in LLC-PK1 cells induced by the glycolysis inhibitor, 2-deoxy-D-glucose (2-DG). … In addition, PEP significantly enhanced the degradation of H2O2. …
NAID 130000425113

製パン用酵母「美の和酵母」の改良研究

関口昭博
群馬県立産業技術センター研究報告 2008年度, 9-12, 2008
NAID 40016992408

Related Pictures

Sigma 15mm f/2.8 EX DG Diagonal Fisheye Using the DG-2 Eyepiece Magnifier on a D 2-デオキシ-D-グルコースと 2006年 07月 07日ニコン製マグニ Nikon BS-1 BS1 BS 1 Hotshoe hot shoe cover Sigma to announce a new 24-35mm f/2 DG HSM DG-2 Eyepiece Magnifier from Nikon

★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	「D」「DG」「dG」

「2-デオキシグルコース」

2-Deoxy-D-glucose^[1]
Names
	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 Registry Number	154-17-6
ChemSpider	388402
	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 ;
IUPHAR ligand	4643
Jmol-3D images	Image
	SMILES O[C@H](C(CO)O[C@H](O)C1)[C@H]1O ;
UNII	9G2MP84A8W
Properties
Chemical formula	C6H12O5
Molar mass	164.16 g/mol
Melting point	142 to 144 °C (288 to 291 °F; 415 to 417 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	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。

「D」

　　[★]

アスパラギン酸
ジヒドロウリジン
遠位の distal,
うつ病 depression
下行結腸 descending colon(大腸内視鏡検査の結果を記載するときに用いる)

「DG」

　　[★]

「dG」

　　[★]

デオキシグアノシン

関: deoxyguanosine

[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" (PDF). 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

匿名

検索

案内

案内

2-DG