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KMID : 0043320080310050587
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Archives of Pharmacal Research
2008 Volume.31 No. 5 p.587 ~ p.593
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A 18F-labeled glucose analog: synthesis using a click labeling method and in vitro evaluation
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Kim Dong-Hyun
Choe Yearn-Seong
Jung Kyung-Ho
Lee Kyung-Han
Choi Joon-Young
Choi Yong
Kim Byung-Tae
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Abstract
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A 18F-labeled glucose analog, 4-[(2-[18F]fluoroethyl)-1-(β-d-glucopyranosyl)]-1H-1,2,3-triazole ([18F]1), was synthesized using a click labeling method and evaluated in vitro for its cellular transportation via glucose transporter (Glut-1) and its potential as a hexokinase substrate. The click labeling method was superior to conventional labeling method, due to a higher decay-corrected radiochemical yield (30% vs. 21%), higher specific activity (59.9 GBq/μmol vs. 23.5 GBq/μmol), and shorter synthesis time (75?80 min vs. 95?100 min). In vitro evaluation demonstrated that [18F]1 does not act as a hexokinase substrate and has low and non-specific uptake by SNU-C5 cells. These results suggest that click chemistry offers a rapid and efficient radiolabeling method which does not require the protection of functional groups, although a triazole moiety at C1 of [18F]1 is incompatible for hexokinase phosphorylation and facilitative diffusion via Glut-1.
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KEYWORD
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18F-labeled glucose analog, Glucopyranosyl azide, 4-[18F]fluoro-1-butyne, Click chemistry, Hexokinase, Glut-1
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