Self-assembly of azamacrocyclic ligands into vesicular structures: from design to functional properties and applications

Abstract

We report on the design and synthesis of novel scorpiand-like macrocyclic ligands that self-assemble into vesicular structures. These ligands, derived from a 6-(2-aminoethyl)-3,6,9-triaza-1-(2,6)-pyridinacyclo-decaphane scaffold, are functionalized with hydrophobic alkyl chains to facilitate vesicle formation. Their properties in solution and their complexation with Cu(II) are thoroughly investigated. These supramolecular assemblies were characterized using TEM and DLS. The studied systems were non-toxic as inferred from an HET-CAM assay. Additionally, the copper complexes exhibit varying degrees of superoxide dismutase (SOD)-like activity, underscoring their potential as enzyme mimetics. Our findings highlight the promise of these macrocyclic ligands as building blocks for functional materials with applications in drug delivery and other biomedical fields in that they combine efficient vesicle formation with SOD-like activity.