Mette Irene Theilgaard Simonsen

Last-Step Pd-Mediated [C-11]CO Labeling of a Moxestrol-Conjugated o-lodobenzyl Alcohol: From Model Experiments to in Vivo Positron Emission Tomography Studies

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

  • Thomas Cornilleau, Univ Bordeaux, Centre National de la Recherche Scientifique (CNRS), Communaute d'Universites et Etablissements d'Aquitaine (ComUE), CNRS, Inst Sci Mol, UMR 5255
  • ,
  • Mette Simonsen
  • Maylou Vang, Univ Bordeaux, Centre National de la Recherche Scientifique (CNRS), Communaute d'Universites et Etablissements d'Aquitaine (ComUE), CNRS, CBMN, UMR 5248
  • ,
  • Nada Taib-Maamar, Univ Bordeaux, Centre National de la Recherche Scientifique (CNRS), Communaute d'Universites et Etablissements d'Aquitaine (ComUE), CNRS, CBMN, UMR 5248
  • ,
  • Jean Dessolin, Univ Bordeaux, Centre National de la Recherche Scientifique (CNRS), Communaute d'Universites et Etablissements d'Aquitaine (ComUE), CNRS, CBMN, UMR 5248
  • ,
  • Helene Audrain
  • Philippe Hermange, Univ Bordeaux, Centre National de la Recherche Scientifique (CNRS), Communaute d'Universites et Etablissements d'Aquitaine (ComUE), CNRS, Inst Sci Mol, UMR 5255
  • ,
  • Eric Fouquet, Univ Bordeaux, Centre National de la Recherche Scientifique (CNRS), Communaute d'Universites et Etablissements d'Aquitaine (ComUE), CNRS, Inst Sci Mol, UMR 5255

The fast, efficient, and functional group tolerant last-step radiolabeling of bioconjugates is crucial for positron emission tomography (PET) applications. In this context, o-iodobenzyl alcohol based structures were identified as ideal tags for an easy Pd-catalyzed carbonylation after bioconjugation, and a moxestrol-conjugated precursor was chosen as the model compound for the further studies. Despite scale and time constraints, conditions developed with [C-12]CO and [C-13]CO were easily transferred to the C-11 isotope, and the desired radioactive product was obtained in amounts up to 740 MBq with radiochemical purities higher than 99%. Radio-high-performance liquid chromatography analyses of rat blood samples demonstrated excellent in vivo stability within the time of the acquisition. MicroPET-magnetic resonance imaging showed excretion pathways similar to moxestrol, and molecular modeling was also performed to evaluate the potential ability of this conjugate to bind estrogen receptors alpha. Thus, being both synthetically and biologically suitable, this strategy clears the path to potential novel biotracers for preclinical PET imaging.

Original languageEnglish
JournalBioconjugate Chemistry
Volume28
Issue11
Pages (from-to)2887-2894
Number of pages8
ISSN1043-1802
DOIs
Publication statusPublished - Nov 2017

    Research areas

  • PALLADIUM-CATALYZED CARBONYLATION, ESTROGEN-RECEPTOR, SILACARBOXYLIC ACIDS, PET TRACERS, MONOXIDE, RADIOPHARMACEUTICALS, CANCER

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