title: A (18)F-labeled glucose analog: synthesis using a click labeling method and in vitro evaluation.
abstract: A (18)F-labeled glucose analog, 4-[(2-[(18)F]fluoroethyl)-1-(beta-D: -glucopyranosyl)]-1H-1,2,3-triazole ([(18)F]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/mumol vs. 23.5 GBq/mumol), and shorter synthesis time (75-80 min vs. 95-100 min). In vitro evaluation demonstrated that [(18)F]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 [(18)F]1 is incompatible for hexokinase phosphorylation and facilitative diffusion via Glut-1.
authors.affiliation: Department of Nuclear Medicine, Samsung Medical Center, Sungkyunkwan University School of Medicine, Kangnam-ku, Seoul, 135-710, Korea.
authors.forename: Dong Hyun
authors.initials: DH
authors.lastname: Kim
authors.forename: Yearn Seong
authors.initials: YS
authors.lastname: Choe
authors.forename: Kyung-Ho
authors.initials: KH
authors.lastname: Jung
authors.forename: Kyung-Han
authors.initials: KH
authors.lastname: Lee
authors.forename: Joon Young
authors.initials: JY
authors.lastname: Choi
authors.forename: Yong
authors.initials: Y
authors.lastname: Choi
authors.forename: Byung-Tae
authors.initials: BT
authors.lastname: Kim
mesh_terms: D045744:Cell Line, Tumor; D004355:Drug Stability; D005462:Fluorine Radioisotopes; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D051272:Glucose Transporter Type 1 / Q000378:metabolism; D006593:Hexokinase / Q000737:chemistry; D006801:Humans; D066298:In Vitro Techniques; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
chemical_list: C530808:4-(2-fluoroethyl)-1-glucopyranosyl-1H-1,2,3-triazole; D005462:Fluorine Radioisotopes; D051272:Glucose Transporter Type 1; D019275:Radiopharmaceuticals; D014230:Triazoles; D006593:Hexokinase; D005947:Glucose