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Issue 28, 2017
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[18F]Fluoroalkyl azides for rapid radiolabeling and (Re)investigation of their potential towards in vivo click chemistry

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Abstract

In recent years, radiofluorinated alkyl azides have been reported for click radiolabeling and pretargeted PET imaging, but only little is known about the biodistribution and metabolism of these compounds. In this work, we present a significantly improved procedure for the synthesis of [18F]fluoroethyl azide and reinvestigated this radiolabeled probe in detail showing poor stability and very restricted suitability for in vivo application. Therefore, modified low-molecular-weight [18F]fluoroalkyl azides were developed. Propargyl-tagged endomorphin-1 (as model compound) was successfully radiolabeled in high yield and short reaction time making these probes useful and efficient bioorthogonal tools for rapid radiolabeling. Biodistribution, pharmacokinetics and in vivo stability were studied by preclinical PET/MR scanning and metabolite analysis. The results of this study revealed only limited applicability of [18F]fluoroalkyl azides for in vivo application.

Graphical abstract: [18F]Fluoroalkyl azides for rapid radiolabeling and (Re)investigation of their potential towards in vivo click chemistry

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Supplementary files

Article information


Submitted
08 Apr 2017
Accepted
27 Jun 2017
First published
27 Jun 2017

This article is Open Access

Org. Biomol. Chem., 2017,15, 5976-5982
Article type
Paper

[18F]Fluoroalkyl azides for rapid radiolabeling and (Re)investigation of their potential towards in vivo click chemistry

C. Denk, M. Wilkovitsch, P. Skrinjar, D. Svatunek, S. Mairinger, C. Kuntner, T. Filip, J. Fröhlich, T. Wanek and H. Mikula, Org. Biomol. Chem., 2017, 15, 5976
DOI: 10.1039/C7OB00880E

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