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Facile synthesis of N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB) for protein labeling

✍ Scribed by G. Tang; Wenbin Zeng; Meixiang Yu; G. Kabalka

Publisher
John Wiley and Sons
Year
2008
Tongue
French
Weight
122 KB
Volume
51
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

An efficient preparation of N‐succinimidyl 4‐[^18^F]fluorobenzoate ([^18^F]SFB) based on a convenient three‐step, one‐pot procedure is described. [^18^F]Fluorination of the precursor ethyl 4‐(trimethylammonium triflate)benzoate gave ethyl 4‐[^18^F]fluorobenzoate. Saponification of the ethyl 4‐[^18^F]fluorobenzoate with aqueous tetrapropylammonium hydroxide yielded the corresponding 4‐[^18^F]fluorobenzoate salt ([^18^F]FBA), which was then treated with N,N,N,N′‐tetramethyl‐O‐(N‐succinimidyl)uronium hexafluorophosphate. The purified [^18^F]SFB was used for the labeling of Avastin^™^ (Bevacizumab) through [^18^F]fluorobenzoylation of the Avastin's α‐amino groups. The decay‐corrected radiochemical yields of [^18^F]SFB were as high as 44% (based on [^18^F]fluoride (n=10) with a synthesis time of less than 60 min. [^18^F]Avastin was produced in decay‐corrected radiochemical yields of up to 42% (n=5) within 30 min (based on [^18^F]SFB). The radiochemical purities of [^18^F]SFB and [^18^F]Avastin were greater than 95%. Copyright © 2008 John Wiley & Sons, Ltd.

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