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Investigation of the complexation of nat Zr(IV) and 89 Zr(IV) by hydroxypyridinones for the development of chelators for PET imaging applications

Abstract : Three hydroxypyridinone (HOPO) positional isomers – 1,2-HOPO (L 1 H) and its water soluble analogue (L 1' H), 3,2-HOPO (L 2 H) and 3,4-HOPO (L 3 H) have been investigated for the complexation of Zr(IV). Potentiometric and UV-Vis spectrometric studies show a higher thermodynamic stability for the formation of Zr(L 1') 4 in comparison with Zr(L 2) 4 and Zr(L 3) 4 as well as a higher kinetic inertness in competition studies with EDTA or Fe 3+ at a radiotracer concentration with 89 Zr. Besides the low pK a of L 1 H or L 1' H (pK a = 5.01) in comparison with L 2 H and L 3 H (pK a = 8.83 and 9.55, respectively), the higher stability of Zr(L 1') 4 can be attributed in part to the presence of the amide group next to the chelating oxygen that induces intramolecular H-bond and amide/π interactions that were observed by X-ray crystallography and confirmed by quantum chemical calculations. The data presented here indicate that the 1,2-HOPO L 1' exhibits the best characteristics for Zr(IV) complexation. However, 3,2-HOPO and 3,4-HOPO patterns, if appropriately tuned, for instance with the addition of an amide group as in the 1,2-HOPO ligand, may also become interesting alternatives for the design of Zr(IV) chelators with improved characteristics for applications in nuclear imaging with 89 Zr.
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Submitted on : Monday, March 27, 2017 - 3:51:56 PM
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François Guérard, Maryline Beyler, Y.-S Lee, Raphaël Tripier, Jean-François Gestin, et al.. Investigation of the complexation of nat Zr(IV) and 89 Zr(IV) by hydroxypyridinones for the development of chelators for PET imaging applications. Dalton Transactions, Royal Society of Chemistry, 2017, 46, pp.4749-4758. ⟨10.1039/c6dt04625h⟩. ⟨inserm-01496515⟩

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