NMR studies of inclusion complexation of the pyrrolizidine alkaloid retronecine and p-sulfonic acid calix[6]arene

Accidental or intentional drug toxicity in humans and animals is a major concern and the search for detoxificant agents is a challenge. Pyrrolizidine-producing forages are a threat not only to livestock, but also to humans as a consequence of food contamination. Supramolecular systems are promising as detoxificant agents by decreasing the bioavailability of toxic compounds in biological environment. Cyclodextrin and calix[ n ]arenes are well known hosts for a variety of molecules and/or ions. Surprisingly, only few studies describe the potential of calix[ n ]arenes as host for toxic molecules. This study focused on the use of NMR techniques as tools for the investigation of the interactions between p -sulfonic acid calix[6]arene and retronecine, a toxic pyrrolizidine alkaloid.