Synthesis of Glyco-Cluster-Modified Cyclodextrins and Dual Recognition for Lectin Proteins and Drugs

Abstract

The efficient synthesis of the high mannose-type oligosaccharide-branched cyclodextrins was carried out. Evaluation of the dual molecular recognition consisting of saccharide-recognition with concanavalin A of the lectin protein, and the inclusion interactions with immobilized cholic acid and doxorubicin as a model drug analyzed by SPR assay. The high mannosyl type oligosaccharide-branched CD (M6CD and M7CD) showed a tight interaction both with lectin and a drug, showing a K_a of 10⁷M^-1 or more. The number of sugar antennas and the length of the spacer arm are quite important for the dual recognition with protein and drug. We can foresee applications of the sugar cluster-branched CD to a targeting drug delivery system.