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

Bioconjugate Chemistry
Thomas CornilleauEric Fouquet

Abstract

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 [12C]CO and [13C]CO were easily transferred to the 11C 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 α. Thus, being both synthetically and biologically suitable, this strategy clears the path to potential novel biotracers for preclinical PET imaging.

References

Aug 1, 1983·Journal of Steroid Biochemistry·J SalmonJ P Raynaud
Oct 24, 1997·Nature·A M BrzozowskiM Carlquist
Nov 28, 2002·Nuclear Medicine and Biology·Eric D Hostetler, H Donald Burns
Feb 20, 2004·Chemical Communications : Chem Comm·Helene AudrainDirk Bender
May 1, 2007·EMBO Reports·Kendall W NettlesGeoffrey L Greene
Jul 7, 2007·Physiological Reviews·Nina HeldringJan-Ake Gustafsson
Feb 22, 2008·Current Medicinal Chemistry·M AllardM Szlosek-Pinaud
Apr 23, 2008·Chemical Reviews·Simon M AmetameyPius August Schubiger
May 12, 2009·Angewandte Chemie·Anne BrennführerMatthias Beller
Sep 21, 2010·Advanced Drug Delivery Reviews·Kai Chen, Peter S Conti
Jan 6, 2011·Chemistry : a European Journal·Philip W MillerRamon Vilar
Dec 17, 2011·Nuclear Medicine and Biology·Filippo LodiStefano Boschi
Oct 9, 2012·Chemical Reviews·Xiao-Feng WuMatthias Beller
Oct 2, 2013·The Lancet Oncology·Michel van KruchtenGeke A P Hospers
Nov 8, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Damien JamesEric Fouquet
Nov 29, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Hancheng Cai, Peter S Conti
Jan 16, 2014·Journal of Labelled Compounds & Radiopharmaceuticals·Steven KealeyPhilip W Miller
Jul 6, 2014·Chemical Society Reviews·Wen Tang, Matthew L Becker
Jan 9, 2015·Journal of the American Chemical Society·Thomas L AndersenTroels Skrydstrup
Feb 17, 2015·Journal of Labelled Compounds & Radiopharmaceuticals·Gunnar Antoni
Feb 18, 2015·Journal of Labelled Compounds & Radiopharmaceuticals·Obaidur Rahman
Jan 12, 2016·Chemical Reviews·Sean PreshlockVéronique Gouverneur
Jun 17, 2016·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Geraldine J LiaoDavid A Mankoff
Jan 5, 2017·Bioorganic & Medicinal Chemistry Letters·Samira OsatiJohan E van Lier

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Citations

Jul 21, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Morgan CormierPhilippe Hermange

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