Synthesis, structure, and evaluation of a β-cyclodextrin-artificial carbohydrate conjugate for use as a doxorubicin-carrying molecule

Abstract

This paper describes the synthesis of a β-cyclodextrin (β-CyD) derivative conjugated with a C,C-glucopyranoside containing a benzene unit. Its doxorubicin-inclusion ability and structure are also discussed. SPR analysis revealed that the β-CyD conjugate had a high inclusion association value of 3.8×10(6)M(-1) for immobilized doxorubicin. NMR structural analysis suggested that its high doxorubicin-inclusion ability was due to the formation of the inclusion complex as a result of the π-π stacking interaction between the benzene ring of the conjugate and the A ring of doxorubicin.

Keywords: Conjugate with a carbohydrate; Cyclodextrin; Doxorubicin; Drug carrier; NMR; Stacking complex.