Journal of Physical Chemistry B, Vol.115, No.5, 1268-1274, 2011
Cooperative Binding and Stabilization of the Medicinal Pigment Curcumin by Diamide Linked gamma-Cyclodextrin Dimers: A Spectroscopic Characterization
Diamide linked gamma-cyclodextrin (gamma-CD) dimers are used to capture curcumin and suppress its decomposition in water. In this study, succinamide and urea linked gamma-CD dimers joined through the C6(A) carbon on each gamma-CD are used. The gamma-CD dimers, 66 gamma CD(2)su and 66 gamma CD(2)ur, 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 666 gamma CD(2)su and 66yCD(2)ur has high stability constants of 8.7 x 10 M-1 and 2.0 x 10(6) M-1, respectively. In addition, 2D H-1-NOESY NMR results show specific hydrogen interactions in the association of curcumin with 66 gamma CD(2)su and 66yCD2ur, consistent with the cooperative binding of curcumin by both gamma-CD annuli of 66 gamma CD(2)su and 66yCD2ur. The interactions between curcumin in the linked gamma-CD dimers and surfactant micelles were studied using fluorescence spectroscopy. While linked gamma-CD dimer-bound curcumin has a negligible fluorescence quantum yield, a significant increase in fluorescence intensity (Phi(a) > 2%) in the presence of micelles suggests that curcumin is delivered to the micelle. The overall results indicate that the diamide linked gamma-CD dimers are highly promising systems for curcumin delivery in vivo due to effective curcumin stabilization.