Combining Desferriferrioxamine B and 1‐Hydroxy‐2‐Piperidone ((PIPO)H) to Chelate Zirconium. Solution Structure of a Model Complex of the [ 89 Zr]Zr−DFOcyclo*−mAb Radioimmunoconjugate - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue ChemPlusChem Année : 2024

Combining Desferriferrioxamine B and 1‐Hydroxy‐2‐Piperidone ((PIPO)H) to Chelate Zirconium. Solution Structure of a Model Complex of the [ 89 Zr]Zr−DFOcyclo*−mAb Radioimmunoconjugate

Résumé

89Zr−immunoPET is a hot topic as 89Zr cumulates the advantages of 64Cu and 124I without their drawbacks. We report the synthesis of a model ligand of a chiral bioconjugable tetrahydroxamic chelator combining the desferriferrioxamine B siderophore and 1-hydroxy-2-piperidone ((PIPO)H), a chiral cyclic hydroxamic acid derivative, and the study by NMR spectroscopy of its zirconium complex. Nuclear Overhauser effect measurements (ROESY) indicated that the complex exists in the form of two diastereomers, in 77 : 23 ratio, resulting from the combination of the central chiralities at the 3-C of the (PIPO)H component and at the Zr4+ cation. The 44 lowest energy structures out of more than 1000 configurations/conformations returned by calculations based on density functional theory were examined. Comparison of the ROESY data and the calculated interatomic H⋅⋅⋅H distances allowed us to select the most probable configuration and conformations of the major complex.
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hal-04570228 , version 1 (06-05-2024)

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Floriane Mangin, Osian Fonquernie, Pawel Jewula, Stéphane Brandès, Marie‐josé Penouilh, et al.. Combining Desferriferrioxamine B and 1‐Hydroxy‐2‐Piperidone ((PIPO)H) to Chelate Zirconium. Solution Structure of a Model Complex of the [ 89 Zr]Zr−DFOcyclo*−mAb Radioimmunoconjugate. ChemPlusChem, In press, ⟨10.1002/cplu.202400062⟩. ⟨hal-04570228⟩
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