Inclusion complexing by water-soluble β-cyclodextrin polymers

Abstract

Cross-linked β-cyclodextrin with a molecular weight of less than 10000 has good solubility in water, and it is a better inclusion complexing agent than the parent β-cyclodextrin. By including lipophilic guest molecules into the apolar cyclodextrin cavity, their apparent lipophilicity is reduced because the outer surface of the molecular ‘wrapping’ (the crosslinked β-CD) is highly hydrophilic. The relative stability of the inclusion complexes can be rapidly determined by reversed-phase thin-layer chromatography. The reversed-phase TLC behaviour of 25 triphenylmethane derivatives and analogues were studied in the presence of β-cyclodextrin polymers containing neutral and carboxyl groups. Increasing the molecular weight results in an increased complex-forming capacity. The carboxyl group modifies the accessibility of the CD cavity which in turn results in increased or decreased complex stability, depending on the guest molecule. The presence of organic solvents diminishes the stability of the CD complexes.