Literature DB >> 30349147

Copper-Mediated Nucleophilic Radiobromination of Aryl Boron Precursors: Convenient Preparation of a Radiobrominated PARP-1 Inhibitor.

Dong Zhou1, Wenhua Chu1, Thomas Voller1, John A Katzenellenbogen2.   

Abstract

The copper-mediated nucleophilic radiobromination of aryl boron precursors with a radiobromide ion is a novel radiolabeling method that is efficient and robust. High radiochemical conversion (RCC) was observed using a variety of solvents, temperatures and catalysts. The reaction is also clean and is feasible for purification to obtain high chemical and radiochemical purity. This method provides a very useful route for the preparation of radiobrominated pharmaceuticals, including a radiobromine labeled PARP-1 inhibitor, and it is a valuable addition to the family of copper-mediated radiolabeling processes.

Entities:  

Keywords:  Auger electron radiation; Labelling method; PET imaging; boron reagents; bromine-76; bromine-77; nucleophilic radiobromination

Year:  2018        PMID： 30349147      PMCID： PMC6195330          DOI： 10.1016/j.tetlet.2018.04.024

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  16 in total

1.  Radiosynthesis of SPECT tracers via a copper mediated 123I iodination of (hetero)aryl boron reagents.

Authors:  Thomas C Wilson; Greg McSweeney; Sean Preshlock; Stefan Verhoog; Matthew Tredwell; Thomas Cailly; Véronique Gouverneur
Journal:  Chem Commun (Camb)       Date:  2016-11-03       Impact factor: 6.222

2.  [11C]Cyanation of arylboronic acids in aqueous solutions.

Authors:  Longle Ma; Michael S Placzek; Jacob M Hooker; Neil Vasdev; Steven H Liang
Journal:  Chem Commun (Camb)       Date:  2017-06-05       Impact factor: 6.222

3.  No-carrier-added radiobromination via cuprous chloride-assisted nucleophilic aromatic bromodeiodination.

Authors:  S M Moerlein; D R Hwang; M J Welch
Journal:  Int J Rad Appl Instrum A       Date:  1988

4.  Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors.

Authors:  Dong Zhou; Sung Hoon Kim; Wenhua Chu; Thomas Voller; John A Katzenellenbogen
Journal:  J Labelled Comp Radiopharm       Date:  2017-06-14       Impact factor: 1.921

5.  Alcohol-Enhanced Cu-Mediated Radiofluorination.

Authors:  Johannes Zischler; Niklas Kolks; Daniel Modemann; Bernd Neumaier; Boris D Zlatopolskiy
Journal:  Chemistry       Date:  2017-01-18       Impact factor: 5.236

6.  Non-invasive PET Imaging of PARP1 Expression in Glioblastoma Models.

Authors:  Brandon Carney; Giuseppe Carlucci; Beatriz Salinas; Valentina Di Gialleonardo; Susanne Kossatz; Axel Vansteene; Valerie A Longo; Alexander Bolaender; Gabriela Chiosis; Kayvan R Keshari; Wolfgang A Weber; Thomas Reiner
Journal:  Mol Imaging Biol       Date:  2016-06       Impact factor: 3.488

7.  Bromination from the macroscopic level to the tracer radiochemical level: (76)Br radiolabeling of aromatic compounds via electrophilic substitution.

Authors:  Dong Zhou; Haibing Zhou; Carl C Jenks; Jason S Lewis; John A Katzenellenbogen; Michael J Welch
Journal:  Bioconjug Chem       Date:  2009-04       Impact factor: 4.774

8.  A general copper-mediated nucleophilic 18F fluorination of arenes.

Authors:  Matthew Tredwell; Sean M Preshlock; Nicholas J Taylor; Stefan Gruber; Mickael Huiban; Jan Passchier; Joël Mercier; Christophe Génicot; Véronique Gouverneur
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

9.  Synthesis and Evaluation of a Radioiodinated Tracer with Specificity for Poly(ADP-ribose) Polymerase-1 (PARP-1) in Vivo.

Authors:  Filip Zmuda; Gaurav Malviya; Adele Blair; Marie Boyd; Anthony J Chalmers; Andrew Sutherland; Sally L Pimlott
Journal:  J Med Chem       Date:  2015-10-27       Impact factor: 7.446

10.  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
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  8 in total

1.  Radiosynthesis and PET Bioimaging of 76Br-Bedaquiline in a Murine Model of Tuberculosis.

Authors:  Alvaro A Ordonez; Laurence S Carroll; Sudhanshu Abhishek; Filipa Mota; Camilo A Ruiz-Bedoya; Mariah H Klunk; Alok K Singh; Joel S Freundlich; Ronnie C Mease; Sanjay K Jain
Journal:  ACS Infect Dis       Date:  2019-07-29       Impact factor: 5.084

2.  Exploration of alcohol-enhanced Cu-mediated radiofluorination toward practical labeling.

Authors:  Dong Zhou; Wenhua Chu; John A Katzenellenbogen
Journal:  J Labelled Comp Radiopharm       Date:  2021-10-19       Impact factor: 1.921

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

4.  Improved production of 76Br, 77Br and 80mBr via CoSe cyclotron targets and vertical dry distillation.

Authors:  Paul A Ellison; Aeli P Olson; Todd E Barnhart; Sabrina L V Hoffman; Sean W Reilly; Mehran Makvandi; Jennifer L Bartels; Dhanabalan Murali; Onofre T DeJesus; Suzanne E Lapi; Bryan Bednarz; Robert J Nickles; Robert H Mach; Jonathan W Engle
Journal:  Nucl Med Biol       Date:  2019-09-05       Impact factor: 2.947

5.  PARP Theranostic Auger Emitters Are Cytotoxic in BRCA Mutant Ovarian Cancer and Viable Tumors from Ovarian Cancer Patients Enable Ex-Vivo Screening of Tumor Response.

Authors:  Aladdin Riad; Sarah B Gitto; Hwan Lee; Harrison D Winters; Paul M Martorano; Chia-Ju Hsieh; Kuiying Xu; Dalia K Omran; Daniel J Powell; Robert H Mach; Mehran Makvandi
Journal:  Molecules       Date:  2020-12-19       Impact factor: 4.411

6.  A general design of caging-group-free photoactivatable fluorophores for live-cell nanoscopy.

Authors:  Richard Lincoln; Mariano L Bossi; Michael Remmel; Elisa D'Este; Alexey N Butkevich; Stefan W Hell
Journal:  Nat Chem       Date:  2022-07-21       Impact factor: 24.274

7.  Investigation on the reactivity of nucleophilic radiohalogens with arylboronic acids in water: access to an efficient single-step method for the radioiodination and astatination of antibodies.

Authors:  Marion Berdal; Sébastien Gouard; Romain Eychenne; Séverine Marionneau-Lambot; Mikaël Croyal; Alain Faivre-Chauvet; Michel Chérel; Joëlle Gaschet; Jean-François Gestin; François Guérard
Journal:  Chem Sci       Date:  2020-11-23       Impact factor: 9.825

8.  Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations.

Authors:  Christoph Fricke; Kristina Deckers; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-20       Impact factor: 16.823
  8 in total

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