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Journal Article

A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging

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Ritter,  Tobias
Department of Chemistry and Chemical Biology, Harvard University ;
Division of Nuclear Medicine and Molecular Imaging, Department of Radiology, Massachusetts General Hospital;
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Supporting Information-om6b00059_si_001.pdf
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Citation

Hoover, A. J., Lazari, M., Ren, H., Narayanam, M. K., Murphy, J. M., van Dam, R. M., et al. (2016). A Transmetalation Reaction Enables the Synthesis of [18F]5-Fluorouracil from [18F]Fluoride for Human PET Imaging. Organometallics, 35(7), 1008-1014. doi:10.1021/acs.organomet.6b00059.


Cite as: http://hdl.handle.net/21.11116/0000-0000-FBD6-4
Abstract
Translation of new 18F-fluorination reactions to produce radiotracers for human positron emission tomography (PET) imaging is rare because the chemistry must have useful scope and the process for 18F-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful 18F-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer. In this article we present chemistry and process innovations that culminate in the first production from [18F]fluoride of human doses of [18F]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [18F]5-fluorouracil precursor. Routine production of >10 mCi doses of [18F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [18F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated 18F-fluorination.