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Nuklearmedizin 2024; 63(05): 300-305
DOI: 10.1055/a-2365-8054
Original Article

18F-labelled gentiobiose as potential PET-radiotracer for specific bacterial imaging: precursor synthesis, radiolabelling and in vitro evaluation

18F-markierte Gentiobiose als potenzieller PET-Radiotracer für die spezifische Bildgebung bakterieller Infektionen: Precursorsynthese, Radiomarkierung und in vitro-Evaluation
Felicitas Landau
1   European Institute for Molecular Imaging, University of Münster, Münster, Germany (Ringgold ID: RIN9185)
2   Department of Nuclear Medicine, University Hospital Münster, Münster, Germany (Ringgold ID: RIN39069)
,
Sven Hermann
1   European Institute for Molecular Imaging, University of Münster, Münster, Germany (Ringgold ID: RIN9185)
,
Sonja Schelhaas
1   European Institute for Molecular Imaging, University of Münster, Münster, Germany (Ringgold ID: RIN9185)
,
Michael Schäfers
1   European Institute for Molecular Imaging, University of Münster, Münster, Germany (Ringgold ID: RIN9185)
2   Department of Nuclear Medicine, University Hospital Münster, Münster, Germany (Ringgold ID: RIN39069)
,
Silke Niemann
3   Institute of Medical Microbiology, University Hospital Münster, Münster, Germany (Ringgold ID: RIN39069)
,
Andreas Faust
1   European Institute for Molecular Imaging, University of Münster, Münster, Germany (Ringgold ID: RIN9185)
› InstitutsangabenGefördert durch: Deutsche Forschungsgemeinschaft Cells in Motion cluster of excellence, Collaborative Research Centre (CRC) 1450–4314608
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Abstract

Aim Bacterial infections are a clinical challenge, requiring fast and specific diagnosis to ensure effective treatment. Therefore, this project is dedicated to development of positron emission tomography (PET) radiotracers specifically targeting bacteria. Unlike previously developed bacteria-specific radiotracers, which are successful in detecting Gram-negative bacteria, tracers capable of imaging Gram-positive infections are still lacking.

Methods The disaccharide gentiobiose as abundant part of the cell wall of Gram-positive bacteria could fill this gap. Herein, the synthesis and evaluation of 2‘-deoxy-2‘-[18F]fluorogentiobiose ([18F]FLA280) is reported. The precursor for radiolabelling was obtained from a convergent synthesis under application of a benzylidene/benzyl group protecting strategy.

Results The first catalytic hydrogenation in 18F-radiochemistry is reported as proof of concept. The deprotection was carried out without any side product formation, giving the final radiotracer [18F]FLA280 in good radiochemical yield and excellent radiochemical purity. [18F]FLA280 was proven to be stable in murine and human blood serum for 120 minutes and was subjected to in vitro bacterial uptake studies towards S. aureus and E. coli resulting in a low bacterial uptake.

Conclusion The observed bacterial uptake indicates that [18F]FLA280 may be not a promising tracer candidate for in vivo translation and alternative candidates particularly for Gram-positive bacteria are required. However, further development on the concept of labelled carbohydrates and cell wall building blocks might be promising.

Keywords

18F-labelling - disaccharides - carbohydrate chemistry - bacterial imaging - PET

Supplementary Material



Publikationsverlauf

Eingereicht: 02. April 2024

Angenommen nach Revision: 12. Juli 2024

Artikel online veröffentlicht:
31. Juli 2024

© 2024. Thieme. All rights reserved.

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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