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Radiosyntheses and reactivities of novel [18F]2-fluoroethyl arylsulfonates

✍ Scribed by John L. Musachio; Jay Shah; Victor W. Pike

Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
148 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

[^18^F]2‐Fluoroethyl tosylate ([^18^F]FEOX, X=Ts) is widely used for labeling radiotracers for positron emission tomography (PET). Little work has been reported on syntheses of other [^18^F]2‐fluoroethyl arylsulfonates ([^18^F]FEOX) that bear a less electron‐rich aryl group, even though these might offer enhanced reactivities. Thus, a series of novel [^18^F]FEOX (X=benzenesulfonyl, brosyl, nosyl, 3,4‐dibromobenzenesulfonyl) were synthesized and reactivities compared to [^18^F]FEOTs. Precursors for radiolabeling (bis‐ethylene glycol arylsulfonates) and reference FEOX were synthesized (alcohol+arylsulfonyl chloride+KOSiMe~3~ in THF). Regardless of substitution pattern, [^18^F]FEOX (110°C, 5 min, acetonitrile) were obtained in similar decay‐corrected isolated radiochemical yields (RCY; 47–53%). All [^18^F]FEOX gave excellent RCYs (64–87%) of the dopamine uptake radioligand, [^18^F]FECNT (130°C, 10 min, acetonitrile). The 3,4‐dibromobenzensulfonate gave the highest RCY of [^18^F]FECNT (87%) and this HPLC‐purified labeling agent was used directly for efficient [^18^F]FECNT production. When the secondary aniline of an amyloid probe (HM‐IMPY) or p‐nitrophenol was reacted with [^18^F]FEOX, RCYs were appreciably higher for brosylate and nosylate than for tosylate, while 3,4‐dibromobenzenesulfonate again gave the highest RCY. Owing to the high reactivity of the new [^18^F]FEOX and their ease of syntheses via stable precursors, such agents (particularly 3,4‐dibromobenzenesulfonate) should be considered as alternatives to [^18^F]FEOTs. Copyright © 2005 John Wiley & Sons, Ltd.

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