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 66γCD 2su 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 66γCD 2su 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.
Original language | English |
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Pages (from-to) | 1268-1274 |
Number of pages | 7 |
Journal | Journal of Physical Chemistry B |
Volume | 115 |
Issue number | 5 |
DOIs | |
Publication status | Published - 10 Feb 2011 |