The radioactively labeled compound [18F]fluorodeoxyglucose (FDG) is used to measure glucose uptake in cells. FDG, a derivative of glucose in which the C2 hydroxyl is replaced with fluorine, is phosphorylated to FDG-6-phosphate upon entering the cell but cannot proceed any further through glycolysis. The phosphorylated FDG remains in the cell, and its presence can be detected and quantitated, providing information on the rate of glucose uptake. (Cancer cells take up glucose particularly rapidly.)
a. Draw the structure of FDG.
b. Why does phosphorylation trap the FDG in the cell?
c. Why is FDG unable to proceed through glycolysis past the hexokinase reaction? (Hint: When glucose-6-phosphate is converted to fructose-6-phosphate, the ring opens, the isomerization reaction takes place, and then the ring closes again.)
d. Is FDG taken up only by cancer cells?
The radioactively labeled compound [18F]fluorodeoxyglucose (FDG) is used to measure glucose uptake in cells. FDG, a derivative of glucose in which the C2 hydroxyl is replaced with fluorine, is phosphorylated to FDG-6-phosphate upon entering the cell but cannot proceed any further through glycolysis. The phosphorylated FDG remains in the cell, and its presence can be detected and quantitated, providing information on the rate of glucose uptake. (Cancer cells take up glucose particularly rapidly.)
a. Draw the structure of FDG.
b. Why does phosphorylation trap the FDG in the cell?
c. Why is FDG unable to proceed through glycolysis past the hexokinase reaction? (Hint: When glucose-6-phosphate is converted to fructose-6-phosphate, the ring opens, the isomerization reaction takes place, and then the ring closes again.)
d. Is FDG taken up only by cancer cells?
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