BAILLY, Thibaud; BODIN, Sacha; GONCALVES, Victor; DENAT, Franck; MORGAT, Clement; PRIGNON, Aurelie; VALVERDE, Ibai E

doi:10.1021/acsmedchemlett.3c00057

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BAILLY, Thibaud

BODIN, Sacha
Institut de Neurosciences cognitives et intégratives d'Aquitaine [INCIA]

GONCALVES, Victor

Idioma

Article de revue

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ACS Medicinal Chemistry Letters. 2023-05-11, vol. 14, n° 5, p. 636-644

Resumen en inglés

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 SAr 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 and (receptor binding affinity, biodistribution, imaging) as an illustration that the assembly methodology preserves the tumor targeting properties of the ligands.< Leer menos

Palabras clave en inglés

Bioconjugation

Click chemistry

Drug delivery

Heterobivalent ligands

Radiopharmaceuticals

URI

https://oskar-bordeaux.fr/handle/20.500.12278/183228

DOI

http://dx.doi.org/10.1021/acsmedchemlett.3c00057

Proyecto ANR

France Life Imaging - ANR-11-INBS-0006

Centros de investigación

Institut de neurosciences cognitives et intégratives d'Aquitaine (INCIA) - UMR 5287