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

This paper describes the synthesis of a beta-cyclodextrin (beta-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 beta-CyD conjugate had a high inclusion association value of 3.8 x 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 pi-pi stacking interaction between the benzene ring of the conjugate and the A ring of doxorubicin. (c) 2015 Elsevier Ltd. All rights reserved.