2-deoxy- D- glucose

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Structural formula
Structural formula of 2-deoxy-D-glucose
General
Surname 2-deoxy- D- glucose
other names
  • 2-deoxy- D -arabinohexose
  • 2-deoxyglucose
Molecular formula C 6 H 12 O 5
External identifiers / databases
CAS number 154-17-6
EC number 205-823-0
ECHA InfoCard 100.005.295
PubChem 108223
ChemSpider 388402
DrugBank DB08831
Wikidata Q3266534
properties
Molar mass 164.16 g mol −1
Physical state

firmly

Melting point

146-147 ° C

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Deoxy- D -glucose is a chemical compound from the group of carbohydrates . It is an analogue of glucose .

properties

Physical Properties

2- Deoxy - D -glucose is a solid with a melting point of 146–147 ° C

Biological properties

It is taken up into cells by glucose transporters . It inhibits glycolysis by inhibiting glucose-6-phosphate isomerase . Defined by hexokinase phosphate 6-2-deoxy-glucose to phosphorylated , the 6-isomerase glucose-phosphate can not be further processed by and competitively inhibits - as with the similar 2- fluorodeoxyglucose . In addition, the hexokinase is 2-deoxy-glucose-6-phosphate noncompetitive inhibited, thereby already less glucose-6-phosphate is formed in the cell - as well as in the similar 2-fluorodeoxyglucose. As a result, 2-deoxy-glucose-6-phosphate accumulates in the cell . As a result, the cellular concentration of adenosine triphosphate (ATP) decreases . In vitro , 2-deoxy-glucose promotes autophagy , the formation of reactive oxygen species and activates AMP-activated protein kinase (AMPK). In addition, the protein kinase PERK is activated, whereby the translation initiation factor eIF-2α is phosphorylated and thus inactivated, whereby translation and consequently cell growth is inhibited. In addition, 2-deoxy- D -glucose inhibits angiogenesis and the metastasis of tumors . The pentose phosphate pathway is also inhibited by 2-deoxy- D -glucose. Because of these various effects, 2-deoxy- D- glucose is being studied in combination with fenofibrate for the treatment of tumors. Because of the inhibition of glycolysis by 2-deoxy- D -glucose, epileptic seizures are reduced, which is why it is being investigated for the treatment of epilepsy.

Since 2-deoxy- D -glucose is also an analogue of mannose (the epimer of glucose at position C2), 2-deoxyglucose- GDP is formed from it, which competitively inhibits N- glycosylation - in contrast to the similar 2-fluorodeoxyglucose a fluorine atom at position C2.

2- Deoxy - D -glucose has antiviral properties by inhibiting the replication of the human herpes virus 8 .

The glucose uptake in cells of organisms is examined with 2-deoxy- D -glucose or fluorodeoxyglucose. 2- Deoxy - D -glucose fluoresces in vivo in the near infrared spectrum.

Individual evidence

  1. ↑ a b c d e f g h i Data sheet 2-Deoxy-D-glucose, ≥98% (GC), crystalline from Sigma-Aldrich , accessed on August 31, 2018 ( PDF ).
  2. ↑ a b c d e f g h i H. Xi, M. Kurtoglu, TJ Lampidis: The wonders of 2-deoxy-D-glucose. In: IUBMB Life . Volume 66, number 2, February 2014, pp. 110–121, doi : 10.1002 / iub.1251 (free full text), PMID 24578297 .
  3. ^ A b A. N. Wick, DR Drury, HI Nakada, JB Wolfe: Localization of the primary metabolic block produced by 2-deoxyglucose. In: Journal of Biological Chemistry . Volume 224, Number 2, February 1957, pp. 963-969, PMID 13405925 .
  4. ↑ M. Ralser, MM Wamelink, EA Struys, C. Joppich, S. Krobitsch, C. Jakobs, H. Lehrach: A catabolic block does not sufficiently explain how 2-deoxy-D-glucose inhibits cell growth. In: Proceedings of the National Academy of Sciences . Volume 105, number 46, November 2008, pp. 17807-17811, doi : 10.1073 / pnas.0803090105 , PMID 19004802 , PMC 2584745 (free full text).
  5. ↑ H. Liu, M. Kurtoglu, CL León-Annicchiarico, C. Munoz-Pinedo, J. Barredo, G. Leclerc, J. Merchan, X. Liu, TJ Lampidis: Combining 2-deoxy-D-glucose with fenofibrate leads to tumor cell death mediated by simultaneous induction of energy and ER stress. In: Oncotarget . Volume 7, number 24, June 2016, pp. 36461-36473, doi : 10.18632 / oncotarget.9263 , PMID 27183907 , PMC 5095013 (free full text).
  6. ↑ CE Stafstrom, A. Roopra, TP Sutula: Seizure suppression via glycolysis inhibition with 2-deoxy-D-glucose (2DG). In: Epilepsia . Volume 49 Suppl 8, November 2008, pp. 97-100, doi : 10.1111 / j.1528-1167.2008.01848.x , PMID 19049601 .
  7. ↑ P. Bazzigaluppi, A. Ebrahim Amini, I. Weisspapir, B. Stefanovic, PL Carlen: Hungry Neurons: Metabolic Insights on Seizure Dynamics. In: International Journal of Molecular Sciences . Volume 18, number 11, October 2017, p. 2269, doi : 10.3390 / ijms18112269 , PMID 29143800 , PMC 5713239 (free full text).
  8. ^ Donard Dwyer: Glucose Metabolism in the Brain. Academic Press, 2002, ISBN 978-0-123-66852-3 , p. XIII.
  9. ^ A b J. L. Kovar, W. Volcheck, E. Sevick-Muraca, MA Simpson, DM Olive: Characterization and performance of a near-infrared 2-deoxyglucose optical imaging agent for mouse cancer models. In: Analytical Biochemistry . Volume 384, number 2, January 2009, pp. 254-262, doi : 10.1016 / j.ab.2008.09.050 , PMID 18938129 , PMC 2720560 (free full text).
  10. ↑ Z. Cheng, J. Levi, Z. Xiong, O. Gheysens, S. Keren, X. Chen, SS Gambhir: Near-infrared fluorescent deoxyglucose analogue for tumor optical imaging in cell culture and living mice. In: Bioconjugate Chemistry . Volume 17, number 3, 2006 May-Jun, pp. 662-669, doi : 10.1021 / bc050345c , PMID 16704203 , PMC 3191878 (free full text).