Radiolabelling and evaluation of novel haloethylsulfoxides as PET imaging agents for tumor hypoxia

Nuclear Medicine and Biology
Evelyn LaurensUwe Ackermann

Abstract

The significance of imaging hypoxia with the PET ligand [(18)F]FMISO has been demonstrated in a variety of cancers. However, the slow kinetics of [(18)F]FMISO require a 2-h delay between tracer administration and patient scanning. Labelled chloroethyl sulfoxides have shown faster kinetics and higher contrast than [(18)F]FMISO in a rat model of ischemic stroke. However, these nitrogen mustard analogues are unsuitable for routine production and use in humans. Here we report on the synthesis and in vitro and in vivo evaluation of two novel sulfoxides which we synthesised from a single precursor molecule via either 2-[(18)F]fluoroethyl azide click chemistry or conventional nucleophilic displacement of a chloride leaving group. The yields of the click chemistry approach were 90±5% of [(18)F]2 based on 2-[(18)F]fluoroethyl azide, and the yields for the S(N) reaction were 15±5% of [(18)F]1 based on K[(18)F]F. Both radiotracers underwent metabolism in an in vitro assay using S9 liver fractions with biological half-lives of 32.39 and 43.32 min, respectively. Imaging studies using an SK-RC-52 tumor model in BALB/c nude mice have revealed that only [(18)F]1 is retained in hypoxic tumors, whereas [(18)F]2 is cleared from those tumors at a ...Continue Reading

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Citations

May 15, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eva GalanteErik Arstad
Jul 25, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marc PretzeConstantin Mamat
Apr 29, 2014·Nuclear Medicine and Biology·Evelyn LaurensUwe Ackermann
Jul 9, 2014·BioMed Research International·Kathrin KettenbachTobias L Ross
Jun 14, 2017·Chemical Society Reviews·Dion van der BornDanielle J Vugts
Nov 10, 2015·Nuclear Medicine and Molecular Imaging·Ji Young Choi, Byung Chul Lee
Nov 29, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Melinda Wuest, Frank Wuest
Jul 21, 2016·Journal of Labelled Compounds & Radiopharmaceuticals·Evelyn LaurensUwe Ackermann

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