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

Lookup NU author(s): Dr James KnightORCiD


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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 ([18F]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 thioureacoupled stabilised bombesin peptide (TT-BBN). In both cases, [18F]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 [18F]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. © The Royal Society of Chemistry 2013.

Publication metadata

Author(s): Knight JC, Richter S, Wuest M, Way JD, Wuest F

Publication type: Article

Publication status: Published

Journal: Organic and Biomolecular Chemistry

Year: 2013

Volume: 11

Issue: 23

Pages: 3817-3825

Online publication date: 25/04/2013

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry


DOI: 10.1039/c3ob40548f

PubMed id: 23640655


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