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

Hoover, Andrew J.; Lazari, Mark; Ren, Hong; Narayanam, Maruthi Kumar; Murphy, Jennifer M.; van Dam, R. Michael; Hooker, Jacob M.; Ritter, Tobias

doi:10.1021/acs.organomet.6b00059

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

Journal Article · Sun Feb 14 04:00:00 UTC 2016 · Organometallics

DOI: https://doi.org/10.1021/acs.organomet.6b00059 · OSTI ID:1434480

Hoover, Andrew J. ^[1]; Lazari, Mark ^[2]; Ren, Hong ^[3]; Narayanam, Maruthi Kumar ^[2]; Murphy, Jennifer M. ^[2]; van Dam, R. Michael ^[2]; Hooker, Jacob M. ^[4]; Ritter, Tobias ^[5]

Harvard Univ., Cambridge, MA (United States); Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States
Univ. of California, Los Angeles, CA (United States)
Harvard Univ., Cambridge, MA (United States); Massachusetts General Hospital and Harvard Medical School, Charlestown, MA (United States); Massachusetts General Hospital, Boston, MA (United States)
Massachusetts General Hospital and Harvard Medical School, Charlestown, MA (United States); Massachusetts General Hospital, Boston, MA (United States)
Harvard Univ., Cambridge, MA (United States); Massachusetts General Hospital, Boston, MA (United States); Max-Planck-Institut fur Kohlenforschung, Mulheim an der Ruhr (Germany)

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. Here, 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.

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Research Organization:: Univ. of California, Los Angeles, CA (United States); Massachusetts General Hospital, Boston, MA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)

Grant/Contract Number:: SC0001249; SC0008430

OSTI ID:: 1434480

Journal Information:: Organometallics, Journal Name: Organometallics Journal Issue: 7 Vol. 35; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Automated synthesis of PET radiotracers by copper-mediated ¹⁸ F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation Mossine, Andrew V.; Brooks, Allen F.; Bernard-Gauthier, Vadim Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 61, Issue 3 https://doi.org/10.1002/jlcr.3583	journal	February 2018
Radiosynthesis of the norepinephrine transporter tracer [ ¹⁸ F]NS12137 via copper-mediated ¹⁸ F-labelling Lahdenpohja, Salla; Keller, Thomas; Rajander, Johan Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 62, Issue 6 https://doi.org/10.1002/jlcr.3717	journal	May 2019
Facile 18F labeling of non-activated arenes via a spirocyclic iodonium(III) ylide method and its application in the synthesis of the mGluR5 PET radiopharmaceutical [18F]FPEB Liang, Steven H.; Wang, Lu; Stephenson, Nickeisha A. Nature Protocols, Vol. 14, Issue 5 https://doi.org/10.1038/s41596-019-0149-3	journal	April 2019
Mechanistic studies and radiofluorination of structurally diverse pharmaceuticals with spirocyclic iodonium( iii ) ylides Rotstein, Benjamin H.; Wang, Lu; Liu, Richard Y. Chemical Science, Vol. 7, Issue 7 https://doi.org/10.1039/c6sc00197a	journal	January 2016
Bioconjugated arylpalladium complexes on solid supports for a convenient last-step synthesis of ¹¹ C-labelled tracers for positron emission tomography Tabey, Alexis; Audrain, Hélène; Fouquet, Eric Chemical Communications, Vol. 55, Issue 53 https://doi.org/10.1039/c9cc03215k	journal	January 2019
One-pot synthesis of high molar activity 6-[ ¹⁸ F]fluoro- l -DOPA by Cu-mediated fluorination of a BPin precursor Mossine, Andrew V.; Tanzey, Sean S.; Brooks, Allen F. Organic & Biomolecular Chemistry, Vol. 17, Issue 38 https://doi.org/10.1039/c9ob01758e	journal	January 2019
Fluorination methods for drug discovery and development Richardson, Paul Expert Opinion on Drug Discovery, Vol. 11, Issue 10 https://doi.org/10.1080/17460441.2016.1223037	journal	August 2016
Fast and efficient copper-mediated 18F-fluorination of arylstannanes, aryl boronic acids, and aryl boronic esters without azeotropic drying Lahdenpohja, Salla Orvokki; Rajala, Noora Annika; Rajander, Johan EJNMMI Radiopharmacy and Chemistry, Vol. 4, Issue 1 https://doi.org/10.1186/s41181-019-0079-y	journal	October 2019
Alcohol-Supported Cu-Mediated 18F-Fluorination of Iodonium Salts under “Minimalist” Conditions Orlovskaya, Victoriya V.; Modemann, Daniel J.; Kuznetsova, Olga F. Molecules, Vol. 24, Issue 17 https://doi.org/10.3390/molecules24173197	journal	September 2019
Fluorinated nucleosides as an important class of anticancer and antiviral agents Cavaliere, Alessandra; Probst, Katrin C.; Westwell, Andrew D. Future Medicinal Chemistry, Vol. 9, Issue 15 https://doi.org/10.4155/fmc-2017-0095	journal	October 2017

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

CCDC 1413389: Experimental Crystal Structure Determination: AKAMOQ : potassium tetrakis(μ-hydroxo)-(μ-acetato)-tetrakis(2-nitro-N-(2-(pyridin-2-yl)phenyl)benzenesulfonamido)-tetra-nickel(ii) tetrahydrofuran solvate Hoover, Andrew J.; Lazari, Mark; Ren, Hong https://doi.org/10.5517/ccdc.csd.cc1jfr6x The current record is supplemented by this dataset	dataset	July 2015
CCDC 1413390: Experimental Crystal Structure Determination: AJUXAG : bis(2-nitro-N-(2-(pyridin-2-yl)phenyl)benzenesulfonamidato)-nickel(ii) dichloromethane solvate Hoover, Andrew; Lazari, Mark; Ren, Hong https://doi.org/10.5517/ccdc.csd.cc1jfr7y The current record is supplemented by this dataset	dataset	July 2015
CCDC 1413391: Experimental Crystal Structure Determination: AJUXEK : (2,4-di-t-butoxypyrimidin-5-yl)-(2-nitro-N-(2-(pyridin-2-yl)phenyl)benzenesulfonamidato)-(pyridine)-nickel pyridine solvate Hoover, Andrew J.; Lazari, Mark; Ren, Hong https://doi.org/10.5517/ccdc.csd.cc1jfr8z The current record is supplemented by this dataset	dataset	July 2015

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

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