Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 24, Issue 4, Pages 635-642Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2015.12.030
Keywords
Cyclodextrin; Conjugate with a carbohydrate; Doxorubicin; Drug carrier; Stacking complex; NMR
Funding
- Grants-in-Aid for Scientific Research [25410186] Funding Source: KAKEN
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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.
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