Work

From Desferrioxamine B Umpolung to an Enantiopure Bifunctional Chelator for 89 Zr‐immunoPET

Year: 2025

Type: article

Abstract: Promising results in preclinical diagnosis based on 89 Zr‐immunoPET have fostered the development of efficient chelators for this tetravalent metal. Leads in this area are octadentate ligands obtained by extension of the desferrioxamine B trihydroxamic acid DFO with a fourth bidentate ligand. In the approach reported here, the latter is a natural 6‐membered cyclic hydroxamic acid deriving from ( L )‐ornithine. Its coupling to DFO via an ( L )‐lysine spacer required that the genuine amine function of the DFO terminus be changed to a carboxylic acid. Such a requirement prompted us to explore short sequences of chemical transformations that would challenge total syntheses leading to the same products. As a matter of fact, the target C ‐terminal DFO analogue was obtained in benzyl‐protected form in three steps from commercially available DFO in 16% overall yield. Our short‐step approach allowed us to implement other functionalities without DFO extension: ‐OH, ‐OTs, ‐CHO, ‐C(O)CH 3 , and ‐CH═CH 2 .

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202501114

Authors: Laurie Zujew, Laurent Raibaut, Jean‐Claude Chambron

Institutions: Centre National de la Recherche Scientifique, Institut de Chimie de Strasbourg, Université de Strasbourg

Language: English

Topic: Radiopharmaceutical Chemistry and Applications

Subfield: Radiology, Nuclear Medicine and Imaging

Field: Medicine

Domain: Health Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funders: Université de Strasbourg, Centre National de la Recherche Scientifique