Hydroxypyridinones, HOPOs, are powerful chelating groups for hard metal ions that have been a subject of much investigation due to their therapeutic and diagnostic potential. Several synthetic siderophores, carrying the hydroxypyridinone ligand preorganized on various platforms, have been synthesized and their coordination chemistry and biomedical utility have been studied. This presentation describes a convenient methodology for the preparation of bifunctional 3, 2- HOPO ligands/linkers that will allow the preparation of a new class of siderophores and lanthanide complexing agents. In addition, the bifunctional nature of the linkers facilitates their attachment to various platforms including biomolecules and probes. The key step in the preparation of these linkers involves both intermolecular and intramolecular Grubbs metathesis of precursors prepared from 2,3-dihydroxypyridine. The preparation of the bifunctional ligands as well as examples of their utility to prepare new classes of siderophores will be presented. The choice of substituents X and Y in the bifunctional HOPO linkers allows much flexibility in their attachment to various platforms.

New methodology for the synthesis of an array of bifunctional 3-hydroxy-2-pyridinone ligands for applications to therapeutic and diagnostic metal ion chelation

253rd National Meeting (2017)

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