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Synthesis of ¹⁸F-Fluoroalkyl-ß-D-Glucosides and Their Evaluation as Tracers for Sodium-Dependent Glucose Transporters

¹ Laboratory for Radiopharmaceutical Chemistry and Department of Nuclear Medicine, Universitaire Ziekenhuizen Gasthuisberg, Leuven, Belgium
² Institute of Anatomy and Cell Biology, Bayerische Julius-Maximilians-Universität, Würzburg, Germany

View larger version (11K): [in a new window]   FIGURE 1. Synthesis of precursors for synthesis of -18F-fluoro-n-butyl-ß-D-glucoside (5b) and -18F-fluoro-n-octyl-ß-D-glucoside (5c).

View larger version (9K): [in a new window]   FIGURE 2. Synthesis of 2'-18F-fluoroethyl-ß-D-glucoside (5a), -18F-fluoro-n-butyl-ß-D-glucoside (5b), and -18F-fluoro-n-octyl-ß-D-glucoside (5c).

View larger version (12K): [in a new window]   FIGURE 3. Inhibition of hSGLT1-expressed MDG uptake by compounds 5a, 5b, and 5c. Xenopus oocytes expressing hSGLT1 were incubated for 1 h with Ori buffer with or without 100 µmol/L phlorizin plus 10 µmol/L 14C-MDG and indicated concentrations of compound 5a, 5b, or 5c. Mean values ± SD of phlorizin-inhibited uptake rates measured from pairs of 7–10 oocytes are presented. Michaelis-Menten equation was fitted to data.

View larger version (16K): [in a new window]   FIGURE 4. Test whether compounds 5a, 5b, and 5c are transported substrates of hSGLT1. Xenopus oocytes expressing hSGLT1 were clamped at -50 mV and superfused with sugar-free Ori buffer or with Ori buffer containing 5 mmol/L of MDG, 5a, 5b, or 5c. (A) Typical experiment with 1 oocyte. (B) Mean ± SD values from 4 oocytes are presented.

View larger version (15K): [in a new window]   FIGURE 5. Substrate dependence of hSGLT1-expressed inward currents that are induced by compound 5a. hSGLT1- expressing Xenopus oocytes clamped at -50 mV were superfused with Ori buffer containing indicated concentrations of 5a, and currents induced by 5a were measured. Mean ± SD values from 4 oocytes are presented. Michaelis-Menten equation was fitted to data.

View larger version (90K): [in a new window]   FIGURE 6. Autoradiographic images of mouse kidney slices (10 µm) obtained 30 min after injection of 5a. Images are scaled to maximal pixel intensity. (A) Transverse slice. (B) Coronal slice. (C) Same section as A after staining with hematoxylin-eosin. Kidney areas are indicated as follows: C, cortex; OS, outer stripe of outer medulla; IS, inner stripe of outer medulla; IZ, inner zone of medulla. Bar = 1 mm. (D) Autoradiographic image of mouse kidney slice (25 µm, coronal) obtained 30 min after injection of 11C-methyl--D-glucoside (23).