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Type: Journal article
Title: Cooperative binding and stabilization of the medicinal pigment curcumin by diamide linked γ-Cyclodextrin Dimers: a spectroscopic characterization
Other Titles: Cooperative binding and stabilization of the medicinal pigment curcumin by diamide linked gamma-Cyclodextrin Dimers: a spectroscopic characterization
Author: Harada, T.
Pham, D.
Leung, H.
Ngo, H.
Lincoln, S.
Easton, C.
Kee, T.
Citation: The Journal of Physical Chemistry B: Biophysical Chemistry, Biomaterials, Liquids, and Soft Matter, 2011; 115(5):1268-1274
Publisher: Amer Chemical Soc
Issue Date: 2011
ISSN: 1520-6106
Statement of
Takaaki Harada, Duc-Truc Pham, Mandy H. M. Leung, Huy Tien Ngo, Stephen F. Lincoln, Christopher J. Easton, and Tak W. Kee
Abstract: Diamide linked γ-cyclodextrin (γ-CD) dimers are used to capture curcumin and suppress its decomposition in water. In this study, succinamide and urea linked γ-CD dimers joined through the C6A carbon on each γ-CD are used. The γ-CD dimers, 66γCD2su and 66γCD2ur, show a remarkable ability to suppress the decomposition of curcumin and extend its half-life from less than 30 min to greater than 16 h. The 1:1 association of curcumin with 66γCD2su and 66γCD2ur has high stability constants of 8.7 × 106 M−1 and 2.0 × 106 M−1, respectively. In addition, 2D 1H NOESY NMR results show specific hydrogen interactions in the association of curcumin with 66γCD2su and 66γCD2ur, consistent with the cooperative binding of curcumin by both γ-CD annuli of 66γCD2su and 66γCD2ur. The interactions between curcumin in the linked γ-CD dimers and surfactant micelles were studied using fluorescence spectroscopy. While linked γ-CD dimer-bound curcumin has a negligible fluorescence quantum yield, a significant increase in fluorescence intensity (Φfl > 2%) in the presence of micelles suggests that curcumin is delivered to the micelle. The overall results indicate that the diamide linked γ-CD dimers are highly promising systems for curcumin delivery in vivo due to effective curcumin stabilization.
Keywords: Diamide
Spectrometry, Fluorescence
Magnetic Resonance Spectroscopy
Hydrogen-Ion Concentration
Quantum Theory
Description: Publication Date (Web): December 31, 2010
Rights: Copyright © 2010 American Chemical Society
DOI: 10.1021/jp1096025
Grant ID:
Appears in Collections:Aurora harvest 5
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