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; Bailey, Justin J.; Ichiishi, Naoko; Schirrmacher, Ralf; Sanford, Melanie S.; Scott, Peter J. H.

doi:10.1002/jlcr.3583

Automated synthesis of PET radiotracers by copper-mediated ¹⁸ F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation

Journal Article · Fri Feb 02 04:00:00 EST 2018 · Journal of Labelled Compounds and Radiopharmaceuticals

DOI:https://doi.org/10.1002/jlcr.3583· OSTI ID:1537577

Mossine, Andrew V. ^[1]; Brooks, Allen F. ^[2]; Bernard-Gauthier, Vadim ^[3]; Bailey, Justin J. ^[3]; Ichiishi, Naoko ^[4]; Schirrmacher, Ralf ^[3]; Sanford, Melanie S. ^[4]; ^[2]

Department of Radiology, University of Michigan Medical School, Ann Arbor MI USA; DOE/OSTI
Department of Radiology, University of Michigan Medical School, Ann Arbor MI USA
Medical Isotope and Cyclotron Facility, Cross Cancer Institute, University of Alberta, Edmonton AB Canada
Department of Chemistry, University of Michigan, Ann Arbor MI USA

Not provided.

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

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0012484

OSTI ID:: 1537577

Journal Information:: Journal of Labelled Compounds and Radiopharmaceuticals, Journal Name: Journal of Labelled Compounds and Radiopharmaceuticals Journal Issue: 3 Vol. 61; ISSN 0362-4803

Publisher:: Wiley

Country of Publication:: United States

Language:: English

References (21)

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Preparation and evaluation of L- and D-5-[ 18 F]fluorotryptophan as PET imaging probes for indoleamine and tryptophan 2,3-dioxygenases Tang, Tang; Gill, Herman S.; Ogasawara, Annie Nuclear Medicine and Biology, Vol. 51 https://doi.org/10.1016/j.nucmedbio.2017.05.001	journal	August 2017
Design, synthesis and evaluation of ¹⁸ F-labeled cationic carbonic anhydrase IX inhibitors for PET imaging Zhang, Zhengxing; Lau, Joseph; Zhang, Chengcheng Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 32, Issue 1 https://doi.org/10.1080/14756366.2017.1308928	journal	January 2017
Enhanced copper-mediated ¹⁸ F-fluorination of aryl boronic esters provides eight radiotracers for PET applications Preshlock, Sean; Calderwood, Samuel; Verhoog, Stefan Chemical Communications, Vol. 52, Issue 54 https://doi.org/10.1039/C6CC03295H	journal	January 2016
Copper-Mediated Aromatic Radiofluorination Revisited: Efficient Production of PET Tracers on a Preparative Scale Zlatopolskiy, Boris D.; Zischler, Johannes; Krapf, Philipp Chemistry - A European Journal, Vol. 21, Issue 15 https://doi.org/10.1002/chem.201405586	journal	February 2015
A Kinome-Wide Selective Radiolabeled TrkB/C Inhibitor for in Vitro and in Vivo Neuroimaging: Synthesis, Preclinical Evaluation, and First-in-Human Bernard-Gauthier, Vadim; Bailey, Justin J.; Mossine, Andrew V. Journal of Medicinal Chemistry, Vol. 60, Issue 16 https://doi.org/10.1021/acs.jmedchem.7b00396	journal	July 2017
Synthesis and evaluation of 18 F-labeled CJ-042794 for imaging prostanoid EP4 receptor expression in cancer with positron emission tomography Zhang, Zhengxing; Lau, Joseph; Kuo, Hsiou-Ting Bioorganic & Medicinal Chemistry Letters, Vol. 27, Issue 10 https://doi.org/10.1016/j.bmcl.2017.03.078	journal	May 2017
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Alcohol-Enhanced Cu-Mediated Radiofluorination Zischler, Johannes; Kolks, Niklas; Modemann, Daniel Chemistry - A European Journal, Vol. 23, Issue 14 https://doi.org/10.1002/chem.201604633	journal	January 2017
Copper-Catalyzed [ ¹⁸ F]Fluorination of (Mesityl)(aryl)iodonium Salts Ichiishi, Naoko; Brooks, Allen F.; Topczewski, Joseph J. Organic Letters, Vol. 16, Issue 12 https://doi.org/10.1021/ol501243g	journal	June 2014
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High Affinity Radiopharmaceuticals Based Upon Lansoprazole for PET Imaging of Aggregated Tau in Alzheimer’s Disease and Progressive Supranuclear Palsy: Synthesis, Preclinical Evaluation, and Lead Selection Fawaz, Maria V.; Brooks, Allen F.; Rodnick, Melissa E. ACS Chemical Neuroscience, Vol. 5, Issue 8 https://doi.org/10.1021/cn500103u	journal	June 2014
Development of subnanomolar radiofluorinated (2-pyrrolidin-1-yl)imidazo[1,2-b]pyridazine pan-Trk inhibitors as candidate PET imaging probes Bernard-Gauthier, Vadim; Bailey, Justin J.; Aliaga, Arturo MedChemComm, Vol. 6, Issue 12 https://doi.org/10.1039/C5MD00388A	journal	January 2015
One-step synthesis of 4-[ ¹⁸ F]fluorobenzyltriphenylphosphonium cation for imaging with positron emission tomography : One-step synthesis of Zhang, Zhengxing; Zhang, Chengcheng; Lau, Joseph Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 59, Issue 11 https://doi.org/10.1002/jlcr.3436	journal	August 2016
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Copper-Mediated Radiofluorination of Arylstannanes with [ ¹⁸ F]KF Makaravage, Katarina J.; Brooks, Allen F.; Mossine, Andrew V. Organic Letters, Vol. 18, Issue 20 https://doi.org/10.1021/acs.orglett.6b02911	journal	October 2016
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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