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Automated radiosynthesis of N-(4-[18F]fluorobenzyl)-2-bromoacetamide: an F-18-labeled reagent for the prosthetic radiolabeling of oligonucleotides

✍ Scribed by Ingrid Koslowsky; Soraya Shahhosseini; John Wilson; John Mercer

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

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✦ Synopsis

Abstract

The potential for radiolabeled antisense oligonucleotides to image gene expression combined with the enhanced resolution of positron‐emission tomography justifies the continued interest in the development of oligonucleotides tagged with positron‐emitting radionuclides. The radiolabeling of oligonucleotides is a multi‐step process and may require handling large amounts of radioactivity initially. A previously reported method for radiolabeling oligonucleotides with N‐(4‐[^18^F]fluorobenzyl)‐2‐bromoacetamide was adapted for use in a commercially available automated synthesis unit by linking two reaction trains. The yield of N‐(4‐[^18^F]fluorobenzyl)‐2‐bromoacetamide ranged from 3 to 18% and the synthesis was completed within 1 h. Challenges in using this unit included the maintenance of anhydrous conditions for the effective reduction of 4‐[^18^F]fluorobenzonitrile. Preliminary results indicated that a mean yield of 36% could be obtained upon incubation of an oligonucleotide with N–(4‐[^18^F]fluorobenzyl)‐2‐bromoacetamide. The entire synthesis could be performed within 3 h. Copyright © 2008 John Wiley & Sons, Ltd.

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