Literature DB >> 27693671

Facile room temperature synthesis of fluorine-18 labeled fluoronicotinic acid-2,3,5,6-tetrafluorophenyl ester without azeotropic drying of fluorine-18.

Falguni Basuli1, Xiang Zhang2, Elaine M Jagoda3, Peter L Choyke3, Rolf E Swenson2.   

Abstract

Fluorine-18 labeled fluoronicotinic acid-2,3,5,6-tetrafluorophenyl ester has been successfully synthesized in an unprecedented way by flowing an acetonitrile solution of its quaternary ammonium salt precursor (N,N,N-trimethyl-5-((2,3,5,6-tetrafluorophenoxy)carbonyl)pyridin-2-aminium trifluoromethanesulfonate, 1) through an anion exchange cartridge. The fluorination reaction proceeded at room temperature without azeotropic drying of the fluoride. Over 75% conversion was observed with 10mg of precursor in 2:8, acetonitrile: t-butanol in 1min. The total synthesis time was 5min which is ~30min shorter than the current literature method. Published by Elsevier Inc.

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Year:  2016        PMID: 27693671      PMCID: PMC5118155          DOI: 10.1016/j.nucmedbio.2016.08.008

Source DB:  PubMed          Journal:  Nucl Med Biol        ISSN: 0969-8051            Impact factor:   2.408


  29 in total

1.  2-(3-{1-Carboxy-5-[(6-[18F]fluoro-pyridine-3-carbonyl)-amino]-pentyl}-ureido)-pentanedioic acid, [18F]DCFPyL, a PSMA-based PET imaging agent for prostate cancer.

Authors:  Ying Chen; Mrudula Pullambhatla; Catherine A Foss; Youngjoo Byun; Sridhar Nimmagadda; Srinivasan Senthamizhchelvan; George Sgouros; Ronnie C Mease; Martin G Pomper
Journal:  Clin Cancer Res       Date:  2011-10-31       Impact factor: 12.531

2.  Green approaches to late-stage fluorination: radiosyntheses of (18)F-labelled radiopharmaceuticals in ethanol and water.

Authors:  Megan N Stewart; Brian G Hockley; Peter J H Scott
Journal:  Chem Commun (Camb)       Date:  2015-08-24       Impact factor: 6.222

Review 3.  Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

Authors:  Philip W Miller; Nicholas J Long; Ramon Vilar; Antony D Gee
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Tetrabutylammonium tetra(tert-butyl alcohol)-coordinated fluoride as a facile fluoride source.

Authors:  Dong Wook Kim; Hwan-Jeong Jeong; Seok Tae Lim; Myung-Hee Sohn
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Calculation of positron range and its effect on the fundamental limit of positron emission tomography system spatial resolution.

Authors:  C S Levin; E J Hoffman
Journal:  Phys Med Biol       Date:  1999-03       Impact factor: 3.609

6.  Late-stage [18F]Fluorination: New Solutions to Old Problems.

Authors:  Allen F Brooks; Joseph J Topczewski; Naoko Ichiishi; Melanie S Sanford; Peter J H Scott
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

7.  Rapid synthesis of [18F]FDG without an evaporation step using an ionic liquid.

Authors:  Hyung Woo Kim; Jae Min Jeong; Yun-Sang Lee; Dae Yoon Chi; Kyoo-Hyun Chung; Dong Soo Lee; June-Key Chung; Myung Chul Lee
Journal:  Appl Radiat Isot       Date:  2004-12       Impact factor: 1.513

8.  Direct one-step 18F-labeling of peptides via nucleophilic aromatic substitution.

Authors:  Jessica Becaud; Linjing Mu; Mylène Karramkam; Pius A Schubiger; Simon M Ametamey; Keith Graham; Timo Stellfeld; Lutz Lehmann; Sandra Borkowski; Dietmar Berndorff; Ludger Dinkelborg; Ananth Srinivasan; René Smits; Beate Koksch
Journal:  Bioconjug Chem       Date:  2009-12       Impact factor: 4.774

9.  Automated synthesis of n.c.a. [18F]FDOPA via nucleophilic aromatic substitution with [18F]fluoride.

Authors:  B Shen; W Ehrlichmann; M Uebele; H-J Machulla; G Reischl
Journal:  Appl Radiat Isot       Date:  2009-03-20       Impact factor: 1.513

Review 10.  Late-Stage Fluorination: From Fundamentals to Application.

Authors:  Michael G Campbell; Tobias Ritter
Journal:  Org Process Res Dev       Date:  2014-03-11       Impact factor: 3.317

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  13 in total

Review 1.  18 F-Labeling of Sensitive Biomolecules for Positron Emission Tomography.

Authors:  Hema S Krishnan; Longle Ma; Neil Vasdev; Steven H Liang
Journal:  Chemistry       Date:  2017-09-01       Impact factor: 5.236

2.  Labeling Single Domain Antibody Fragments with Fluorine-18 Using 2,3,5,6-Tetrafluorophenyl 6-[18F]Fluoronicotinate Resulting in High Tumor-to-Kidney Ratios.

Authors:  Zhengyuan Zhou; Darryl McDougald; Nick Devoogdt; Michael R Zalutsky; Ganesan Vaidyanathan
Journal:  Mol Pharm       Date:  2018-11-28       Impact factor: 4.939

3.  Rapid synthesis of maleimide functionalized fluorine-18 labeled prosthetic group using "radio-fluorination on the Sep-Pak" method.

Authors:  Falguni Basuli; Xiang Zhang; Elaine M Jagoda; Peter L Choyke; Rolf E Swenson
Journal:  J Labelled Comp Radiopharm       Date:  2018-05-01       Impact factor: 1.921

4.  Fast indirect fluorine-18 labeling of protein/peptide using the useful 6-fluoronicotinic acid-2,3,5,6-tetrafluorophenyl prosthetic group: A method comparable to direct fluorination.

Authors:  Falguni Basuli; Xiang Zhang; Carolyn C Woodroofe; Elaine M Jagoda; Peter L Choyke; Rolf E Swenson
Journal:  J Labelled Comp Radiopharm       Date:  2017-02-01       Impact factor: 1.921

5.  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

6.  ImmunoPET: Concept, Design, and Applications.

Authors:  Weijun Wei; Zachary T Rosenkrans; Jianjun Liu; Gang Huang; Quan-Yong Luo; Weibo Cai
Journal:  Chem Rev       Date:  2020-03-23       Impact factor: 60.622

7.  Development of [18F]FPy-WL12 as a PD-L1 Specific PET Imaging Peptide.

Authors:  Wojciech G Lesniak; Ronnie C Mease; Samit Chatterjee; Dhiraj Kumar; Ala Lisok; Bryan Wharram; Venkateswara Rao Kalagadda; Leisha A Emens; Martin G Pomper; Sridhar Nimmagadda
Journal:  Mol Imaging       Date:  2019 Jan-Dec       Impact factor: 4.488

8.  A non-anhydrous, minimally basic protocol for the simplification of nucleophilic 18F-fluorination chemistry.

Authors:  J A H Inkster; V Akurathi; A W Sromek; Y Chen; J L Neumeyer; A B Packard
Journal:  Sci Rep       Date:  2020-04-22       Impact factor: 4.379

9.  Fluorine-18-Labeled Antibody Ligands for PET Imaging of Amyloid-β in Brain.

Authors:  Stina Syvänen; Xiaotian T Fang; Rebecca Faresjö; Johanna Rokka; Lars Lannfelt; Dag E Olberg; Jonas Eriksson; Dag Sehlin
Journal:  ACS Chem Neurosci       Date:  2020-11-25       Impact factor: 4.418

10.  Automated Synthesis of Fluorine-18 Labeled CXCR4 Ligand via the Conjugation with Nicotinic Acid N-Hydroxysuccinimide Ester (6-[18F]SFPy).

Authors:  Falguni Basuli; Xiang Zhang; Tim E Phelps; Elaine M Jagoda; Peter L Choyke; Rolf E Swenson
Journal:  Molecules       Date:  2020-08-27       Impact factor: 4.411

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