O. Langer, M. Mitterhauser, W. Wadsak
Jul 1, 2003
Citations
1
Influential Citations
15
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
Fluoroquinolones are an important class of antibiotic agents with a broad spectrum of antibacterial activity. Labelling of fluoroquinolones with fluorine-18 is of interest for the performance of pharmacokinetic measurements and the visualization of bacterial infections in humans with positron emission tomography. A two-step radiosynthetic pathway to prepare fluorine-18-labelled ciprofloxacin (1-cyclopropyl-6-[18F]fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid) has previously been developed. In the present work this approach was applied to the preparation of the structurally related compounds [18F]norfloxacin (1-ethyl-6-[18F]fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid) and [18F]pefloxacin (1-ethyl-6-[18F]fluoro-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-quinoline-3-carboxylic acid). The first step of the radiosynthesis consisted of a 18F for 19F exchange reaction on a 7-chloro-substituted precursor molecule, followed by coupling reactions with the amines piperazine or 1-methylpiperazine. Starting from 51–58 GBq of [18F]fluoride 1.9–2.0 GBq of [18F]norfloxacin or [18F]pefloxacin, ready for intravenous injection, could be obtained in a synthesis time of 130 min (3.5–3.8% overall radiochemical yield). Moreover, the preparation of [18F]levofloxacin ((-)-(S)-9-[18F]fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylicacid) was attempted but failed to afford the desired product in practical amounts. Copyright © 2003 John Wiley & Sons, Ltd.