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Issue 23, 2013
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Synthesis and evaluation of an 18F-labelled norbornene derivative for copper-free click chemistry reactions

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Abstract

The copper-free click chemistry reaction between norbornene and tetrazine species is known to proceed in a rapid, reliable and selective manner under mild conditions. Due to these attractive properties, this reaction has recently been explored as a generally applicable method of bioconjugation. Here, we report a convenient synthetic procedure towards a novel 18F-labelled norbornene derivative ([181818F]NFB) and have evaluated its ability to undergo strain-promoted copper-free click chemistry reactions with two model tetrazine species: an asymmetric dipyridyl tetrazine derivative (Tz) and a tetrazine thiourea-coupled stabilised bombesin peptide (TT-BBN). In both cases, [181818F]NFB was found to undergo rapid and high-yielding click chemistry reactions. Furthermore, as reactions of this type could also potentially be used in vivo to facilitate the development of a novel pretargeting approach for tumour imaging and therapy, we have also assessed the radiopharmacological profile (bioavailability, biodistribution, blood clearance and metabolic stability) of [181818F]NFB in normal BALB/c mice. This radiolabelled compound exhibits both high bioavailability and metabolic stability with approximately 90% remaining intact up to 30 min following administration.

Graphical abstract: Synthesis and evaluation of an 18F-labelled norbornene derivative for copper-free click chemistry reactions

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Publication details

The article was received on 19 Mar 2013, accepted on 24 Apr 2013, published on 25 Apr 2013 and first published online on 25 Apr 2013


Article type: Paper
DOI: 10.1039/C3OB40548F
Citation: Org. Biomol. Chem., 2013,11, 3817-3825
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    Synthesis and evaluation of an 18F-labelled norbornene derivative for copper-free click chemistry reactions

    J. C. Knight, S. Richter, M. Wuest, J. D. Way and F. Wuest, Org. Biomol. Chem., 2013, 11, 3817
    DOI: 10.1039/C3OB40548F

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