Literature DB >> 29561158

Rapid Cu-Catalyzed [211At]Astatination and [125I]Iodination of Boronic Esters at Room Temperature.

Sean W Reilly1, Mehran Makvandi1, Kuiying Xu1, Robert H Mach1.   

Abstract

Access to 211At- and 125I-radiolabeled compounds in excellent RCCs and RCYs was achieved in just 10 min at room temperature using a Cu catalyst. The reaction conditions are applicable to a broad class of aryl and heteroaryl boronic reagents with varying steric and electronic properties as well as late-stage astatination and iodination of anticancer PARP inhibitors. This protocol eliminates the traditional need for toxic organotin reagents, elevated temperatures, and extended reaction times, providing a more practical and environmentally friendly approach to developing α-emitting radiotherapeutics.

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Year:  2018        PMID: 29561158      PMCID: PMC5973503          DOI: 10.1021/acs.orglett.8b00232

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  26 in total

1.  Ionic liquid supported organotin reagents to prepare molecular imaging and therapy agents.

Authors:  Holisoa Rajerison; Djibril Faye; Aurélia Roumesy; Nicolas Louaisil; Fabien Boeda; Alain Faivre-Chauvet; Jean-François Gestin; Stéphanie Legoupy
Journal:  Org Biomol Chem       Date:  2016-02-14       Impact factor: 3.876

2.  Enigmatic astatine.

Authors:  D Scott Wilbur
Journal:  Nat Chem       Date:  2013-03       Impact factor: 24.427

3.  Development of a stable radioiodinating reagent to label monoclonal antibodies for radiotherapy of cancer.

Authors:  D S Wilbur; S W Hadley; M D Hylarides; P G Abrams; P A Beaumier; A C Morgan; J M Reno; A R Fritzberg
Journal:  J Nucl Med       Date:  1989-02       Impact factor: 10.057

4.  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

5.  Radiopharmaceutical chemistry of targeted radiotherapeutics, Part 3: alpha-particle-induced radiolytic effects on the chemical behavior of (211)At.

Authors:  Oscar R Pozzi; Michael R Zalutsky
Journal:  J Nucl Med       Date:  2007-06-15       Impact factor: 10.057

6.  Cu-catalyzed fluorination of diaryliodonium salts with KF.

Authors:  Naoko Ichiishi; Allan J Canty; Brian F Yates; Melanie S Sanford
Journal:  Org Lett       Date:  2013-09-24       Impact factor: 6.005

7.  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

8.  A Radiotracer Strategy to Quantify PARP-1 Expression In Vivo Provides a Biomarker That Can Enable Patient Selection for PARP Inhibitor Therapy.

Authors:  Mehran Makvandi; Kuiying Xu; Brian P Lieberman; Redmond-Craig Anderson; Samuel Sander Effron; Harrison D Winters; Chenbo Zeng; Elizabeth S McDonald; Daniel A Pryma; Roger A Greenberg; Robert H Mach
Journal:  Cancer Res       Date:  2016-06-03       Impact factor: 13.312

9.  Copper-catalyzed [18F]fluorination of (mesityl)(aryl)iodonium salts.

Authors:  Naoko Ichiishi; Allen F Brooks; Joseph J Topczewski; Melissa E Rodnick; Melanie S Sanford; Peter J H Scott
Journal:  Org Lett       Date:  2014-06-03       Impact factor: 6.005

10.  Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids.

Authors:  Andrew V Mossine; Allen F Brooks; Katarina J Makaravage; Jason M Miller; Naoko Ichiishi; Melanie S Sanford; Peter J H Scott
Journal:  Org Lett       Date:  2015-11-14       Impact factor: 6.005

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  20 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.  Targeting PARP-1 with Alpha-Particles Is Potently Cytotoxic to Human Neuroblastoma in Preclinical Models.

Authors:  Mehran Makvandi; Hwan Lee; Laura N Puentes; Sean W Reilly; Komal S Rathi; Chi-Chang Weng; Ho Sze Chan; Catherine Hou; Pichai Raman; Daniel Martinez; Kuiying Xu; Sean D Carlin; Roger A Greenberg; Bruce R Pawel; Robert H Mach; John M Maris; Daniel A Pryma
Journal:  Mol Cancer Ther       Date:  2019-05-09       Impact factor: 6.261

Review 3.  Overview of the Most Promising Radionuclides for Targeted Alpha Therapy: The "Hopeful Eight".

Authors:  Romain Eychenne; Michel Chérel; Férid Haddad; François Guérard; Jean-François Gestin
Journal:  Pharmaceutics       Date:  2021-06-18       Impact factor: 6.321

4.  Synthesis and characterization of [125I]TZ6544, a promising radioligand for investigating sphingosine-1-phosphate receptor 2.

Authors:  Zonghua Luo; Qianwa Liang; Hui Liu; Joshi Sumit; Hao Jiang; Robyn S Klein; Zhude Tu
Journal:  Nucl Med Biol       Date:  2020-07-27       Impact factor: 2.408

5.  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

6.  Synthesis and preliminary evaluation of 211At-labeled inhibitors of prostate-specific membrane antigen for targeted alpha particle therapy of prostate cancer.

Authors:  Ganesan Vaidyanathan; Ronnie C Mease; Il Minn; Jaeyeon Choi; Ying Chen; Hassan Shallal; Choong Mo Kang; Darryl McDougald; Vivek Kumar; Martin G Pomper; Michael R Zalutsky
Journal:  Nucl Med Biol       Date:  2021-01-23       Impact factor: 2.408

7.  PARP Targeted Alpha-Particle Therapy Enhances Response to PD-1 Immune-Checkpoint Blockade in a Syngeneic Mouse Model of Glioblastoma.

Authors:  Hannah Dabagian; Tahereh Taghvaee; Paul Martorano; Daniel Martinez; Minu Samanta; Carolyn M Watkins; Richard Chai; Adam Mansfield; Thomas J Graham; John M Maris; Daniel A Pryma; Robert H Mach; Mehran Makvandi
Journal:  ACS Pharmacol Transl Sci       Date:  2021-01-26

8.  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

9.  Radiosynthesis and Evaluation of Talazoparib and Its Derivatives as PARP-1-Targeting Agents.

Authors:  Dong Zhou; Huaping Chen; Cedric Mpoy; Sadia Afrin; Buck E Rogers; Joel R Garbow; John A Katzenellenbogen; Jinbin Xu
Journal:  Biomedicines       Date:  2021-05-18

10.  Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution.

Authors:  Yoshifumi Shirakami; Tadashi Watabe; Honoka Obata; Kazuko Kaneda; Kazuhiro Ooe; Yuwei Liu; Takahiro Teramoto; Atsushi Toyoshima; Atsushi Shinohara; Eku Shimosegawa; Jun Hatazawa; Koichi Fukase
Journal:  Sci Rep       Date:  2021-06-21       Impact factor: 4.379

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