Literature DB >> 31536095

One-pot synthesis of high molar activity 6-[18F]fluoro-l-DOPA by Cu-mediated fluorination of a BPin precursor.

Andrew V Mossine1, Sean S Tanzey2, Allen F Brooks1, Katarina J Makaravage3, Naoko Ichiishi3, Jason M Miller2, Bradford D Henderson1, Marc B Skaddan4, Melanie S Sanford3, Peter J H Scott2.   

Abstract

A one-pot two-step synthesis of 6-[18F]fluoro-l-DOPA ([18F]FDOPA) has been developed involving Cu-mediated radiofluorination of a pinacol boronate ester precursor. The method is fully automated, provides [18F]FDOPA in good activity yield (104 ± 16 mCi, 6 ± 1%), excellent radiochemical purity (>99%) and high molar activity (3799 ± 2087 Ci mmol-1), n = 3, and has been validated to produce the radiotracer for human use.

Entities:  

Year:  2019        PMID： 31536095      PMCID： PMC6812483          DOI： 10.1039/c9ob01758e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  34 in total

1.  Enhanced copper-mediated (18)F-fluorination of aryl boronic esters provides eight radiotracers for PET applications.

Authors:  Sean Preshlock; Samuel Calderwood; Stefan Verhoog; Matthew Tredwell; Mickael Huiban; Antje Hienzsch; Stefan Gruber; Thomas C Wilson; Nicholas J Taylor; Thomas Cailly; Michael Schedler; Thomas Lee Collier; Jan Passchier; René Smits; Jan Mollitor; Alexander Hoepping; Marco Mueller; Christophe Genicot; Joël Mercier; Véronique Gouverneur
Journal:  Chem Commun (Camb)       Date:  2016-06-28       Impact factor: 6.222

Review 2.  Current status of 18F-DOPA PET imaging in the detection of brain tumor recurrence.

Authors:  Ferdinando Calabria; Giuseppe Lucio Cascini
Journal:  Hell J Nucl Med       Date:  2015-07-20       Impact factor: 1.102

Review 3.  Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Authors:  Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-14       Impact factor: 15.336

4.  Modern carbon-fluorine bond forming reactions for aryl fluoride synthesis.

Authors:  Michael G Campbell; Tobias Ritter
Journal:  Chem Rev       Date:  2014-12-04       Impact factor: 60.622

5.  Copper-Mediated Oxidative Fluorination of Aryl Stannanes with Fluoride.

Authors:  Raymond F Gamache; Christopher Waldmann; Jennifer M Murphy
Journal:  Org Lett       Date:  2016-08-29       Impact factor: 6.005

6.  An azeotropic drying-free approach for copper-mediated radiofluorination without addition of base.

Authors:  Xiang Zhang; Falguni Basuli; Rolf E Swenson
Journal:  J Labelled Comp Radiopharm       Date:  2019-02-20       Impact factor: 1.921

7.  Three-step, "one-pot" radiosynthesis of 6-fluoro-3,4-dihydroxy-L-phenylalanine by isotopic exchange.

Authors:  Franziska M Wagner; Johannes Ermert; Heinz H Coenen
Journal:  J Nucl Med       Date:  2009-09-16       Impact factor: 10.057

Review 8.  6-[18F]fluoro-L-DOPA: a well-established neurotracer with expanding application spectrum and strongly improved radiosyntheses.

Authors:  M Pretze; C Wängler; B Wängler
Journal:  Biomed Res Int       Date:  2014-05-28       Impact factor: 3.411

9.  Development of Customized [18F]Fluoride Elution Techniques for the Enhancement of Copper-Mediated Late-Stage Radiofluorination.

Authors:  Andrew V Mossine; Allen F Brooks; Naoko Ichiishi; Katarina J Makaravage; Melanie S Sanford; Peter J H Scott
Journal:  Sci Rep       Date:  2017-03-22       Impact factor: 4.379

10.  Concerted nucleophilic aromatic substitution with (19)F(-) and (18)F(-).

Authors:  Constanze N Neumann; Jacob M Hooker; Tobias Ritter
Journal:  Nature       Date:  2016-05-18       Impact factor: 49.962
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  13 in total

1.  An Organometallic Gold(III) Reagent for 18F Labeling of Unprotected Peptides and Sugars in Aqueous Media.

Authors:  James W McDaniel; Julia M Stauber; Evan A Doud; Alexander M Spokoyny; Jennifer M Murphy
Journal:  Org Lett       Date:  2022-07-08       Impact factor: 6.072

2.  Synthesis of high-molar-activity [18F]6-fluoro-L-DOPA suitable for human use via Cu-mediated fluorination of a BPin precursor.

Authors:  Andrew V Mossine; Sean S Tanzey; Allen F Brooks; Katarina J Makaravage; Naoko Ichiishi; Jason M Miller; Bradford D Henderson; Thomas Erhard; Christian Bruetting; Marc B Skaddan; Melanie S Sanford; Peter J H Scott
Journal:  Nat Protoc       Date:  2020-04-08       Impact factor: 13.491

3.  Copper-Mediated Late-stage Radiofluorination: Five Years of Impact on Pre-clinical and Clinical PET Imaging.

Authors:  Jay S Wright; Tanpreet Kaur; Sean Preshlock; Sean S Tanzey; Wade P Winton; Liam S Sharninghausen; Nicholas Wiesner; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal:  Clin Transl Imaging       Date:  2020-05-26

Review 4.  Approaches to PET Imaging of Glioblastoma.

Authors:  Lindsey R Drake; Ansel T Hillmer; Zhengxin Cai
Journal:  Molecules       Date:  2020-01-28       Impact factor: 4.411

Review 5.  Advances in the automated synthesis of 6-[18F]Fluoro-L-DOPA.

Authors:  Ângela C B Neves; Ivanna Hrynchak; Inês Fonseca; Vítor H P Alves; Mariette M Pereira; Amílcar Falcão; Antero J Abrunhosa
Journal:  EJNMMI Radiopharm Chem       Date:  2021-03-10

6.  Radiosynthesis and characterization of [18F]BS224: a next-generation TSPO PET ligand insensitive to the rs6971 polymorphism.

Authors:  Sang Hee Lee; Nunzio Denora; Valentino Laquintana; Giuseppe Felice Mangiatordi; Angela Lopedota; Antonio Lopalco; Annalisa Cutrignelli; Massimo Franco; Pietro Delre; In Ho Song; Hye Won Kim; Su Bin Kim; Hyun Soo Park; Kyungmin Kim; Seok-Yong Lee; Hyewon Youn; Byung Chul Lee; Sang Eun Kim
Journal:  Eur J Nucl Med Mol Imaging       Date:  2021-11-16       Impact factor: 9.236

7.  Late-Stage Copper-Catalyzed Radiofluorination of an Arylboronic Ester Derivative of Atorvastatin.

Authors:  Gonçalo S Clemente; Tryfon Zarganes-Tzitzikas; Alexander Dömling; Philip H Elsinga
Journal:  Molecules       Date:  2019-11-20       Impact factor: 4.411

8.  Use of 55 PET radiotracers under approval of a Radioactive Drug Research Committee (RDRC).

Authors:  Isaac M Jackson; So Jeong Lee; Alexandra R Sowa; Melissa E Rodnick; Laura Bruton; Mara Clark; Sean Preshlock; Jill Rothley; Virginia E Rogers; Leslie E Botti; Bradford D Henderson; Brian G Hockley; Jovany Torres; David M Raffel; Allen F Brooks; Kirk A Frey; Michael R Kilbourn; Robert A Koeppe; Xia Shao; Peter J H Scott
Journal:  EJNMMI Radiopharm Chem       Date:  2020-11-11

Review 9.  Nucleophilic Synthesis of 6-l-[18F]FDOPA. Is Copper-Mediated Radiofluorination the Answer?

Authors:  Raisa N Krasikova
Journal:  Molecules       Date:  2020-09-23       Impact factor: 4.411

10.  A concise method for fully automated radiosyntheses of [18F]JNJ-46356479 and [18F]FITM via Cu-mediated 18F-fluorination of organoboranes.

Authors:  Gengyang Yuan; Timothy M Shoup; Sung-Hyun Moon; Anna-Liisa Brownell
Journal:  RSC Adv       Date:  2020-07-02       Impact factor: 4.036
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