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Modular One-Pot Strategy for the Synthesis of Heterobivalent Tracers

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Modular One-Pot Strategy for the Synthesis of Heterobivalent Tracers
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  • Thibaud Bailly
    Thibaud Bailly
    Institut de Chimie Moléculaire de l’Université de Bourgogne, UMR CNRS 6302, Université de Bourgogne, 21000 Dijon, France
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  • Sacha Bodin
    Sacha Bodin
    University of Bordeaux, CNRS, EPHE, INCIA, UMR 5287, Bordeaux F-33000, France
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    Orcidhttps://orcid.org/0000-0001-7331-8536
  • Victor Goncalves
    Victor Goncalves
    Institut de Chimie Moléculaire de l’Université de Bourgogne, UMR CNRS 6302, Université de Bourgogne, 21000 Dijon, France
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    Orcidhttps://orcid.org/0000-0001-9854-4409
  • Franck Denat
    Franck Denat
    Institut de Chimie Moléculaire de l’Université de Bourgogne, UMR CNRS 6302, Université de Bourgogne, 21000 Dijon, France
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  • Clément Morgat
    Clément Morgat
    University of Bordeaux, CNRS, EPHE, INCIA, UMR 5287, Bordeaux F-33000, France
    Nuclear Medicine Department, University Hospital of Bordeaux, Bordeaux F-33000, France
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    Orcidhttps://orcid.org/0000-0002-9432-9223
  • Aurélie Prignon
    Aurélie Prignon
    UMS28 Laboratoire d’Imagerie Moléculaire Positonique (LIMP), Sorbonne Université, Paris 75020, France
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    Orcidhttps://orcid.org/0000-0002-3963-863X
  • Ibai E. Valverde*
    Ibai E. Valverde
    Institut de Chimie Moléculaire de l’Université de Bourgogne, UMR CNRS 6302, Université de Bourgogne, 21000 Dijon, France
    *Mailing Address: Ibai E. Valverde, Institut de Chimie Moléculaire de L’Université de Bourgogne, UMR 6302, Univ. Bourgogne Franche-Comté, 9, Avenue Alain Savary, 21078 Dijon Cedex, France; Email: [email protected], Phone: +33 380 39 90 48.
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    Orcidhttps://orcid.org/0000-0002-5802-4131
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ACS Medicinal Chemistry Letters

Cite this: ACS Med. Chem. Lett. 2023, 14, 5, 636–644
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https://doi.org/10.1021/acsmedchemlett.3c00057
Published April 21, 2023
Copyright © 2023 American Chemical Society
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Abstract

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Bivalent ligands, i.e., molecules having two ligands covalently connected by a linker, have been gathering attention since the first description of their pharmacological potential in the early 80s. However, their synthesis, particularly of labeled heterobivalent ligands, can still be cumbersome and time-consuming. We herein report a straightforward procedure for the modular synthesis of labeled heterobivalent ligands (HBLs) using dual reactive 3,6-dichloro-1,2,4,5-tetrazine as a starting material and suitable partners for sequential SNAr and inverse electron-demand Diels–Alder (IEDDA) reactions. This assembly method conducted in a stepwise or in a sequential one-pot manner provides quick access to multiple HBLs. A conjugate combining ligands toward the prostate-specific membrane antigen (PSMA) and the gastrin-releasing peptide receptor (GRPR) was radiolabeled, and its biological activity was assessed in vitro and in vivo (receptor binding affinity, biodistribution, imaging) as an illustration that the assembly methodology preserves the tumor targeting properties of the ligands.

Copyright © 2023 American Chemical Society

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Supporting Information

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsmedchemlett.3c00057.

  • Synthesis and full characterization of compounds 4 to 22 and [68Ga]22 (γ-HPLC), examples of other compounds synthesized via the one-pot procedure, radiolabeling procedures, and experimental protocols of in vitro and in vivo experiments (PDF)

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This article is cited by 3 publications.

  1. Zhihao Zha, Karl Ploessl, Seok Rye Choi, Ruiyue Zhao, Wenbin Jin, Ran Wang, David Alexoff, Lin Zhu, Hank F. Kung. Lu-177-Labeled Hetero-Bivalent Agents Targeting PSMA and Bone Metastases for Radionuclide Therapy. Journal of Medicinal Chemistry 2023, 66 (17) , 12602-12613. https://doi.org/10.1021/acs.jmedchem.3c01294
  2. Honghu Zhang, Lin Qi, Yi Cai, Xiaomei Gao. Gastrin-releasing peptide receptor (GRPR) as a novel biomarker and therapeutic target in prostate cancer. Annals of Medicine 2024, 56 (1) https://doi.org/10.1080/07853890.2024.2320301
  3. Claudia Chambers, Broc Chitwood, Charles J. Smith, Yubin Miao. Elevating theranostics: The emergence and promise of radiopharmaceutical cell‐targeting heterodimers in human cancers. iRADIOLOGY 2024, 2 (2) , 128-155. https://doi.org/10.1002/ird3.62
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ACS Medicinal Chemistry Letters

Cite this: ACS Med. Chem. Lett. 2023, 14, 5, 636–644
Click to copy citationCitation copied!
https://doi.org/10.1021/acsmedchemlett.3c00057
Published April 21, 2023
Copyright © 2023 American Chemical Society
Request reuse permissions

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