Deoxyglucose: Difference between revisions

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{{PAGENAME}} - a non-metabolizable glucose analog in which the hydroxyl group at position 2 of glucose is replaced by hydrogen, with potential glycolysis inhibiting and antineoplastic activities. Although the exact mechanism of action has yet to be fully elucidated, upon administration of 2-deoxy-d-glucose (2-dg), this agent competes with glucose for uptake by proliferating cells, such as tumor cells. 2-dg inhibits the first step of glycolysis and therefore prevents cellular energy production, which may result in decreased tumor cell proliferation. See 2-deoxy-d-glucose
{{DISPLAYTITLE:Deoxyglucose}}
{{med-stub}}
{{Infobox chemical
{{dictionary-stub2}}
| name = Deoxyglucose
{{short-articles-ni}}
| image = Deoxyglucose_structure.png
| image_size = 200px
| image_alt = Structural formula of deoxyglucose
| pin = 2-Deoxy-D-glucose
| othernames = 2-Deoxyglucose, 2-DG
| section1 = {{Chembox Identifiers
  | CASNo = 154-17-6
  | PubChem = 10690
  | ChemSpiderID = 10241
  | UNII = 2FLV3454XG
  | ChEBI = 42250
  | ChEMBL = 1201190
  | SMILES = C([C@@H]([C@H]([C@H](CO)O)O)O)O
  | InChI = 1S/C6H12O5/c7-1-2-3(8)4(9)5(10)6(11)12/h3-5,7-10H,1-2H2/t3-,4+,5-
  | InChIKey = WQZGKKKJIJFFOK-VFUOTHLCSA-N
}}
| section2 = {{Chembox Properties
  | C = 6
  | H = 12
  | O = 5
  | molar_mass = 164.16 g/mol
  | appearance = White crystalline powder
  | solubility = Soluble in water
}}
}}
 
==Overview==
'''Deoxyglucose''' is a [[glucose]] analog in which the 2-hydroxyl group is replaced by hydrogen, rendering it unable to undergo further glycolysis. It is primarily used in [[biochemical]] research and [[medical imaging]].
 
==Chemical Structure and Properties==
Deoxyglucose is a [[monosaccharide]] with the chemical formula C₆H₁₂O₅. It is structurally similar to glucose, but lacks the hydroxyl group at the second carbon position. This modification prevents it from being fully metabolized by the [[glycolytic pathway]].
 
==Mechanism of Action==
Deoxyglucose is taken up by cells via the same transport mechanisms as glucose, such as the [[GLUT transporters]]. Once inside the cell, it is phosphorylated by [[hexokinase]] to form deoxyglucose-6-phosphate. However, unlike glucose-6-phosphate, deoxyglucose-6-phosphate cannot be further metabolized in the glycolytic pathway, leading to its accumulation within the cell. This accumulation can inhibit glycolysis and [[ATP]] production, affecting cellular metabolism.
 
==Applications in Research==
Deoxyglucose is widely used in research to study [[cellular metabolism]] and [[glucose uptake]]. It is particularly useful in [[cancer research]] to investigate the [[Warburg effect]], where cancer cells exhibit increased glucose uptake and glycolysis.
 
===Use in Medical Imaging===
In [[positron emission tomography]] (PET) imaging, a radiolabeled form of deoxyglucose, typically [[fluorodeoxyglucose]] (FDG), is used to visualize metabolic activity in tissues. FDG-PET scans are valuable in diagnosing and monitoring [[cancer]], as well as assessing [[brain]] and [[heart]] function.
 
==Clinical Implications==
Deoxyglucose has been explored as a potential therapeutic agent due to its ability to inhibit glycolysis. It has been studied in the context of [[cancer therapy]], where it may selectively target cancer cells that rely heavily on glycolysis for energy production.
 
==Safety and Toxicity==
While deoxyglucose is generally considered safe for use in research and imaging, its effects on metabolism can lead to potential side effects. In clinical settings, careful monitoring is required to avoid hypoglycemia and other metabolic disturbances.
 
==Conclusion==
Deoxyglucose is a versatile tool in both research and clinical settings, providing insights into cellular metabolism and offering potential therapeutic avenues. Its role in medical imaging, particularly in PET scans, highlights its importance in modern medicine.
 
{{DEFAULTSORT:Deoxyglucose}}
[[Category:Monosaccharides]]
[[Category:Glucose]]
[[Category:Medical imaging]]
[[Category:Biochemistry]]
[[Category:Cancer research]]

Latest revision as of 17:04, 1 January 2025


Deoxyglucose
Deoxyglucose_structure.png
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

Overview[edit]

Deoxyglucose is a glucose analog in which the 2-hydroxyl group is replaced by hydrogen, rendering it unable to undergo further glycolysis. It is primarily used in biochemical research and medical imaging.

Chemical Structure and Properties[edit]

Deoxyglucose is a monosaccharide with the chemical formula C₆H₁₂O₅. It is structurally similar to glucose, but lacks the hydroxyl group at the second carbon position. This modification prevents it from being fully metabolized by the glycolytic pathway.

Mechanism of Action[edit]

Deoxyglucose is taken up by cells via the same transport mechanisms as glucose, such as the GLUT transporters. Once inside the cell, it is phosphorylated by hexokinase to form deoxyglucose-6-phosphate. However, unlike glucose-6-phosphate, deoxyglucose-6-phosphate cannot be further metabolized in the glycolytic pathway, leading to its accumulation within the cell. This accumulation can inhibit glycolysis and ATP production, affecting cellular metabolism.

Applications in Research[edit]

Deoxyglucose is widely used in research to study cellular metabolism and glucose uptake. It is particularly useful in cancer research to investigate the Warburg effect, where cancer cells exhibit increased glucose uptake and glycolysis.

Use in Medical Imaging[edit]

In positron emission tomography (PET) imaging, a radiolabeled form of deoxyglucose, typically fluorodeoxyglucose (FDG), is used to visualize metabolic activity in tissues. FDG-PET scans are valuable in diagnosing and monitoring cancer, as well as assessing brain and heart function.

Clinical Implications[edit]

Deoxyglucose has been explored as a potential therapeutic agent due to its ability to inhibit glycolysis. It has been studied in the context of cancer therapy, where it may selectively target cancer cells that rely heavily on glycolysis for energy production.

Safety and Toxicity[edit]

While deoxyglucose is generally considered safe for use in research and imaging, its effects on metabolism can lead to potential side effects. In clinical settings, careful monitoring is required to avoid hypoglycemia and other metabolic disturbances.

Conclusion[edit]

Deoxyglucose is a versatile tool in both research and clinical settings, providing insights into cellular metabolism and offering potential therapeutic avenues. Its role in medical imaging, particularly in PET scans, highlights its importance in modern medicine.

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