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Synthesis of [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione: an agent for specific radiolabelling of tyrosine.
Flagothier, Jessica; Warnier, Corentin; Lemaire, Christian et al.
2013In Flagothier, Jessica (Ed.) Journal of Labelled Compounds and Radiopharmaceuticals
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Keywords :
fluorine-18; radiolabeling
Abstract :
[en] Objectives: Metal-free and mild tyrosine modification reactions are an attractive alternative to the commonly used lysine and cysteine modification protocols for peptide and proteins labelling. Recently, Ban and co-workers have reported a tyrosine bioconjugation through ene-type reactions. Cyclic diazodicarboxamides, which are electrophilic compounds, react selectively in o-position on the phenol side chain of tyrosine in mild aqueous conditions and the 1,2,4-triazolidine-3,5-dione linkage is hydrolytically and thermally stable. We herein present the synthesis of [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione and the coupling with N-acyl tyrosine methylamide. Methods: The N,N,N-trimethyl-4-nitrobenzeneammonium trifluoromethanesulfonate 1 was prepared following a procedure previously reported [2]. The [18F]prosthetic group 6, [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione, was synthesized in five steps. Results: The synthesis of the [18F]prosthetic group has been realized with a decay-corrected radiochemical yield of 20% in 90 minutes. The radiochemical yield of the coupling with N-acyl tyrosine methylamide is 40% (DC). This presented synthetic pathway should be easily automated: particulary because the purifications between the different steps are exclusively done on SPE cartridges. Conclusions: We successfully developed an efficient bioconjugation method for fluorine-18 labelling of tyrosine without prior modifications of the peptide in very mild conditions.
Research center :
GIGA CRC (Cyclotron Research Center) In vivo Imaging-Aging & Memory - ULiège
Disciplines :
Chemistry
Author, co-author :
Flagothier, Jessica ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse
Warnier, Corentin ;  Université de Liège - ULiège > Centre de recherches du cyclotron
Lemaire, Christian ;  Université de Liège - ULiège > Centre de recherches du cyclotron
Luxen, André ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse
Language :
English
Title :
Synthesis of [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione: an agent for specific radiolabelling of tyrosine.
Alternative titles :
[en] Synthèse du [18F]4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione: un agent pour le radiomarquage spécifique de la tyrosine.
Publication date :
14 May 2013
Event name :
International symposium of radiopharmaceuticals sciences
Event organizer :
Society Radiopharmaceuticals Sciences
Event place :
Jeju, South Korea
Event date :
du 12 au 17 mai 2013
Audience :
International
Main work title :
Journal of Labelled Compounds and Radiopharmaceuticals
Editor :
Flagothier, Jessica ;  Université de Liège - ULiège > Département de chimie (sciences)
Publisher :
Wiley
Peer reviewed :
Peer reviewed
Funders :
ULiège - Université de Liège [BE]
Available on ORBi :
since 23 May 2013

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