Synthesis of Diverse 11C-Labeled PET Radiotracers via Direct Incorporation of [11C]CO2

Mossine, Andrew V.; Brooks, Allen F.; Jackson, Isaac M.; Quesada, Carole A.; Sherman, Phillip; Cole, Erin L.; Donnelly, David J.; Scott, Peter J.  H.; Shao, Xia

doi:10.1021/acs.bioconjchem.6b00163

Title: Synthesis of Diverse ¹¹C-Labeled PET Radiotracers via Direct Incorporation of [¹¹C]CO₂

Journal Article · Mon Apr 04 00:00:00 EDT 2016 · Bioconjugate Chemistry

DOI:https://doi.org/10.1021/acs.bioconjchem.6b00163· OSTI ID:1467011

Mossine, Andrew V. ^[1]; Brooks, Allen F. ^[1]; Jackson, Isaac M. ^[1]; Quesada, Carole A. ^[1]; Sherman, Phillip ^[1]; Cole, Erin L. ^[2]; Donnelly, David J. ^[2]; Scott, Peter J. H. ^[3]; Shao, Xia ^[1]

Univ. of Michigan Medical School, Ann Arbor, MI (United States). Division of Nuclear Medicine and Dept. of Radiology
Bristol-Myers Squibb Research and Development, Princeton, NJ (United States). Discovery Chemistry Platforms and PET Radiochemical Synthesis
Univ. of Michigan Medical School, Ann Arbor, MI (United States). The Interdepartmental Program in Medicinal Chemistry, Division of Nuclear Medicine and Dept. of Radiology

Three new positron emission tomography (PET) radiotracers of interest to our functional neuroimaging and translational oncology programs have been prepared through new developments in [¹¹C]CO₂ fixation chemistry. [¹¹C]QZ (glutaminyl cyclase) was prepared via a tandem trapping of [¹¹C]CO₂/intramolecular cyclization; [¹¹C]tideglusib (glycogen synthase kinase-3) was synthesized through a tandem trapping of [¹¹C]CO₂ followed by an intermolecular cycloaddition between a [¹¹C]isocyanate and an isothiocyanate to form the 1,2,4-thiadiazolidine-3,5-dione core; [¹¹C]ibrutinib (Bruton’s tyrosine kinase) was synthesized through a HATU peptide coupling of an amino precursor with [¹¹C]acrylic acid (generated from [¹¹C]CO₂ fixation with vinylmagnesium bromide). All radiochemical syntheses are fully-automated on commercial radiochemical synthesis modules and provide radiotracers in 1 – 5% radiochemical yield (non-corrected, based upon [¹¹C]CO₂). In addition, all three radiotracers have advanced to rodent imaging studies and preliminary PET imaging results are also reported.

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Research Organization:: Univ. of Michigan Medical School, Ann Arbor, MI (United States)

Sponsoring Organization:: USDOE; National Institutes of Health (NIH); Alzheimer’s Association

Grant/Contract Number:: SC0012484; T32-EB005172; NIRP-14-305669

OSTI ID:: 1467011

Journal Information:: Bioconjugate Chemistry, Vol. 27, Issue 5; ISSN 1043-1802

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 23 works

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References (39)

Molecular Imaging with PET Ametamey, Simon M.; Honer, Michael; Schubiger, Pius August Chemical Reviews, Vol. 108, Issue 5 https://doi.org/10.1021/cr0782426	journal	May 2008
PET and the role of in vivo molecular imaging in personalized medicine Pither, Richard Expert Review of Molecular Diagnostics, Vol. 3, Issue 6 https://doi.org/10.1586/14737159.3.6.703	journal	November 2003
Positron emission tomography molecular imaging for drug development: PET for drug development Matthews, Paul M.; Rabiner, Eugenii A.; Passchier, Jan British Journal of Clinical Pharmacology, Vol. 73, Issue 2 https://doi.org/10.1111/j.1365-2125.2011.04085.x	journal	January 2012
Synthesis of ¹¹ C, ¹⁸ F, ¹⁵ O, and ¹³ N Radiolabels for Positron Emission Tomography Miller, Philip W.; Long, Nicholas J.; Vilar, Ramon Angewandte Chemie International Edition, Vol. 47, Issue 47 https://doi.org/10.1002/anie.200800222	journal	November 2008
Methods for the Incorporation of Carbon-11 To Generate Radiopharmaceuticals for PET Imaging Scott, Peter J. H. Angewandte Chemie International Edition, Vol. 48, Issue 33 https://doi.org/10.1002/anie.200901481	journal	August 2009
Development of carbon-11 labelled PET tracers-radiochemical and technological challenges in a historic perspective: Development of carbon-11 labelled PET tracers Antoni, Gunnar Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 58, Issue 3 https://doi.org/10.1002/jlcr.3258	journal	February 2015
An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles Baumann, Marcus; Baxendale, Ian R. Beilstein Journal of Organic Chemistry, Vol. 9 https://doi.org/10.3762/bjoc.9.265	journal	January 2013
Automated production of [11C]acetate and [11C]palmitate using a modified GE Tracerlab FXC-Pro Runkle, Adam C.; Shao, Xia; Tluczek, Louis J. M. Applied Radiation and Isotopes, Vol. 69, Issue 4 https://doi.org/10.1016/j.apradiso.2011.01.002	journal	April 2011
CuI-Catalyzed 11C Carboxylation of Boronic Acid Esters: A Rapid and Convenient Entry to 11C-Labeled Carboxylic Acids, Esters, and Amides Riss, Patrick J.; Lu, Shuiyu; Telu, Sanjay Angewandte Chemie International Edition, Vol. 51, Issue 11 https://doi.org/10.1002/anie.201107263	journal	February 2012
Synthesis of [ ¹¹ C]Bexarotene by Cu-Mediated [ ¹¹ C]Carbon Dioxide Fixation and Preliminary PET Imaging Rotstein, Benjamin H.; Hooker, Jacob M.; Woo, Jiyeon ACS Medicinal Chemistry Letters, Vol. 5, Issue 6 https://doi.org/10.1021/ml500065q	journal	March 2014
11CO2 fixation: a renaissance in PET radiochemistry Rotstein, Benjamin H.; Liang, Steven H.; Holland, Jason P. Chemical Communications, Vol. 49, Issue 50 https://doi.org/10.1039/c3cc42236d	journal	January 2013
Synthesis of 11C-Labelled Symmetrical Ureas via the Rapid Incorporation of [11C]CO2 into Aliphatic and Aromatic Amines Dheere, Abdul; Bongarzone, Salvatore; Taddei, Carlotta Synlett, Vol. 26, Issue 16 https://doi.org/10.1055/s-0034-1381055	journal	September 2015
Rapid and efficient synthesis of [11C]ureas via the incorporation of [11C]CO2 into aliphatic and aromatic amines Haji Dheere, Abdul Karim; Yusuf, Nadiya; Gee, Antony Chemical Communications, Vol. 49, Issue 74 https://doi.org/10.1039/c3cc44046j	journal	January 2013
Radiosynthesis and ex vivo evaluation of [11C-carbonyl]carbamate- and urea-based monoacylglycerol lipase inhibitors Hicks, Justin W.; Parkes, Jun; Tong, Junchao Nuclear Medicine and Biology, Vol. 41, Issue 8 https://doi.org/10.1016/j.nucmedbio.2014.05.001	journal	September 2014
Synthesis and preclinical evaluation of [11C-carbonyl]PF-04457845 for neuroimaging of fatty acid amide hydrolase Hicks, Justin W.; Parkes, Jun; Sadovski, Oleg Nuclear Medicine and Biology, Vol. 40, Issue 6 https://doi.org/10.1016/j.nucmedbio.2013.04.008	journal	August 2013
Towards the preparation of radiolabeled 1-aryl-3-benzyl ureas: Radiosynthesis of [11C-carbonyl] AR-A014418 by [11C]CO2 fixation Hicks, Justin W.; Wilson, Alan A.; Rubie, Elizabeth A. Bioorganic & Medicinal Chemistry Letters, Vol. 22, Issue 5 https://doi.org/10.1016/j.bmcl.2011.12.139	journal	March 2012
Synthesis and Application of Isocyanates Radiolabeled with Carbon-11 Wilson, Alan A.; Garcia, Armando; Houle, Sylvain Chemistry - A European Journal, Vol. 17, Issue 1 https://doi.org/10.1002/chem.201002345	journal	November 2010
One-Pot, Direct Incorporation of [ ¹¹ C]CO ₂ into Carbamates Hooker, Jacob M.; Reibel, Achim T.; Hill, Sidney M. Angewandte Chemie International Edition, Vol. 48, Issue 19 https://doi.org/10.1002/anie.200900112	journal	April 2009
Radiosynthesis and Evaluation of [ ¹¹ C- Carbonyl ]-Labeled Carbamates as Fatty Acid Amide Hydrolase Radiotracers for Positron Emission Tomography Wilson, Alan A.; Hicks, Justin W.; Sadovski, Oleg Journal of Medicinal Chemistry, Vol. 56, Issue 1 https://doi.org/10.1021/jm301492y	journal	December 2012
Radiosynthesis of [11C]SL25.1188 via [11C]CO2 fixation for imaging monoamine oxidase B Vasdev, Neil; Sadovski, Oleg; Garcia, Armando Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 54, Issue 10 https://doi.org/10.1002/jlcr.1908	journal	July 2011
Direct fixation of [ ¹¹ C]-CO ₂ by amines: formation of [ ¹¹ C-carbonyl]-methylcarbamates Wilson, Alan A.; Garcia, Armando; Houle, Sylvain Org. Biomol. Chem., Vol. 8, Issue 2 https://doi.org/10.1039/B916419G	journal	January 2010
[11C]Carbon Disulfide: A Versatile Reagent for PET Radiolabelling Miller, Philip W.; Bender, Dirk Chemistry - A European Journal, Vol. 18, Issue 2 https://doi.org/10.1002/chem.201103128	journal	December 2011
Structure–activity relationship of human glutaminyl cyclase inhibitors having an N-(5-methyl-1H-imidazol-1-yl)propyl thiourea template Tran, Phuong-Thao; Hoang, Van-Hai; Thorat, Shivaji A. Bioorganic & Medicinal Chemistry, Vol. 21, Issue 13 https://doi.org/10.1016/j.bmc.2013.04.005	journal	July 2013
Evidence for Irreversible Inhibition of Glycogen Synthase Kinase-3β by Tideglusib Domínguez, Juan Manuel; Fuertes, Ana; Orozco, Leyre Journal of Biological Chemistry, Vol. 287, Issue 2 https://doi.org/10.1074/jbc.M111.306472	journal	January 2012
Ibrutinib: a first in class covalent inhibitor of Bruton's tyrosine kinase Davids, Matthew S.; Brown, Jennifer R. Future Oncology, Vol. 10, Issue 6 https://doi.org/10.2217/fon.14.51	journal	May 2014
Highlighting the versatility of the Tracerlab synthesis modules. Part 2: fully automated production of [11C]-labeled radiopharmaceuticals using a Tracerlab FXC-Pro: Production of [11C] radiopharmaceuticals using a Tracerlab FXC-Pro Shao, Xia; Hoareau, Raphaël; Runkle, Adam C. Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 54, Issue 14 https://doi.org/10.1002/jlcr.1937	journal	October 2011
Glutaminyl cyclase inhibition attenuates pyroglutamate Aβ and Alzheimer's disease–like pathology Schilling, Stephan; Zeitschel, Ulrike; Hoffmann, Torsten Nature Medicine, Vol. 14, Issue 10 https://doi.org/10.1038/nm.1872	journal	September 2008
Glutaminyl Cyclase in Human Cortex: Correlation with (pGlu)-Amyloid-β Load and Cognitive Decline in Alzheimer's Disease Morawski, Markus; Schilling, Stephan; Kreuzberger, Moritz Journal of Alzheimer's Disease, Vol. 39, Issue 2 https://doi.org/10.3233/JAD-131535	journal	January 2014
Synthesis and evaluation of [ ¹¹ C]PBD150, a radiolabeled glutaminyl cyclase inhibitor for the potential detection of Alzheimer's disease prior to amyloid β aggregation Brooks, Allen F.; Jackson, Isaac M.; Shao, Xia MedChemComm, Vol. 6, Issue 6 https://doi.org/10.1039/C5MD00148J	journal	January 2015
The First Potent Inhibitors for Human Glutaminyl Cyclase: Synthesis and Structure−Activity Relationship Buchholz, Mirko; Heiser, Ulrich; Schilling, Stephan Journal of Medicinal Chemistry, Vol. 49, Issue 2 https://doi.org/10.1021/jm050756e	journal	January 2006
Molecular cloning and expression of glycogen synthase kinase-3/factor A. Woodgett, J. R. The EMBO Journal, Vol. 9, Issue 8 https://doi.org/10.1002/j.1460-2075.1990.tb07419.x	journal	August 1990
The GSK3 hypothesis of Alzheimer’s disease: GSK3 and Alzheimer’s disease Hooper, Claudie; Killick, Richard; Lovestone, Simon Journal of Neurochemistry, Vol. 104, Issue 6 https://doi.org/10.1111/j.1471-4159.2007.05194.x	journal	December 2007
Role of glycogen synthase kinase-3 in Alzheimer’s disease pathogenesis and glycogen synthase kinase-3 inhibitors Avila, Jesús; Wandosell, Francisco; Hernández, Félix Expert Review of Neurotherapeutics, Vol. 10, Issue 5 https://doi.org/10.1586/ern.10.40	journal	May 2010
Synthesis and evaluation of [11C]PyrATP-1, a novel radiotracer for PET imaging of glycogen synthase kinase-3β (GSK-3β) Cole, Erin L.; Shao, Xia; Sherman, Phillip Nuclear Medicine and Biology, Vol. 41, Issue 6 https://doi.org/10.1016/j.nucmedbio.2014.03.025	journal	July 2014
Synthesis and Initial in Vivo Studies with [ ¹¹ C]SB-216763: The First Radiolabeled Brain Penetrative Inhibitor of GSK-3 Li, Lei; Shao, Xia; Cole, Erin L. ACS Medicinal Chemistry Letters, Vol. 6, Issue 5 https://doi.org/10.1021/acsmedchemlett.5b00044	journal	March 2015
A phase 2 trial of the GSK-3 inhibitor tideglusib in progressive supranuclear palsy: Tideglusib in PSP Tolosa, Eduardo; Litvan, Irene; Höglinger, Günter U. Movement Disorders, Vol. 29, Issue 4 https://doi.org/10.1002/mds.25824	journal	February 2014
A Phase II Trial of Tideglusib in Alzheimer's Disease Lovestone, Simon; Boada, Mercè; Dubois, Bruno Journal of Alzheimer's Disease, Vol. 45, Issue 1 https://doi.org/10.3233/JAD-141959	journal	March 2015
N-Chlorosuccinimide is a convenient oxidant for the synthesis of 2,4-disubstituted 1,2,4-thiadiazolidine-3,5-diones Nasim, Shama; Crooks, Peter A. Tetrahedron Letters, Vol. 50, Issue 3 https://doi.org/10.1016/j.tetlet.2008.10.136	journal	January 2009
Toward Prediction of Efficacy of Chemotherapy: A Proof of Concept Study in Lung Cancer Patients Using [11C]docetaxel and Positron Emission Tomography van der Veldt, A. A. M.; Lubberink, M.; Mathijssen, R. H. J. Clinical Cancer Research, Vol. 19, Issue 15 https://doi.org/10.1158/1078-0432.CCR-12-3779	journal	April 2013

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Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions Deng, Xiaoyun; Rong, Jian; Wang, Lu Angewandte Chemie International Edition, Vol. 58, Issue 9 https://doi.org/10.1002/anie.201805501	journal	January 2019
Rapid and Efficient Synthesis of ¹¹ C-Labeled Benzimidazolones Using [ ¹¹ C]Carbon Dioxide Horkka, Kaisa; Dahl, Kenneth; Bergare, Jonas ChemistrySelect, Vol. 4, Issue 6 https://doi.org/10.1002/slct.201803561	journal	February 2019
Direct Incorporation of [ ¹¹ C]CO ₂ into Asymmetric [ ¹¹ C]Carbonates Haji Dheere, Abdul Karim; Bongarzone, Salvatore; Shakir, Dinah Journal of Chemistry, Vol. 2018 https://doi.org/10.1155/2018/7641304	journal	December 2018
Recent progress in [ ¹¹ C]carbon dioxide ([ ¹¹ C]CO ₂ ) and [ ¹¹ C]carbon monoxide ([ ¹¹ C]CO) chemistry Taddei, Carlotta; Gee, Antony D. Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 61, Issue 3 https://doi.org/10.1002/jlcr.3596	journal	February 2018
Late-Stage Isotopic Carbon Labeling of Pharmaceutically Relevant Cyclic Ureas Directly from CO ₂ Del Vecchio, Antonio; Caillé, Fabien; Chevalier, Arnaud Angewandte Chemie International Edition, Vol. 57, Issue 31 https://doi.org/10.1002/anie.201804838	journal	July 2018
Late-Stage Isotopic Carbon Labeling of Pharmaceutically Relevant Cyclic Ureas Directly from CO ₂ Del Vecchio, Antonio; Caillé, Fabien; Chevalier, Arnaud Angewandte Chemie, Vol. 130, Issue 31 https://doi.org/10.1002/ange.201804838	journal	July 2018

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Title: Synthesis of Diverse ¹¹C-Labeled PET Radiotracers via Direct Incorporation of [¹¹C]CO₂