Mono-Dendronized beta-Cyclodextrin Derivatives as Multitasking Containers for Curcumin. Impacting Its Solubility, Loading, and Tautomeric Form
Por:
Citlali Cabrera-Quinones, Neyra, Jose Lopez-Mendez, Luis, Ramos, Estrella, Rojas-Aguirre, Yareli, GUADARRAMA, PATRICIA
Publicada:
24 feb 2022
Resumen:
In this study, three mono-dendronized beta-cyclodextri n (beta CD)
derivatives (beta CD-1G, beta CD-2G, and beta CD-3G) were used as
multitasking containers of curcumin (CUR) to influence its aqueous
solubility and tautomerism, both of which are related to its biological
activity. We evaluated the relevant physicochemical properties of these
containers associated with their potential hosting capacity. All
mono-dendronized derivatives exhibited enhanced solubility in different
solvents, including water, in comparison with native beta CD. Gas-phase
geometry optimizations by density functional theory (DFT) confirmed that
none of the dendrons blocked the passage of CUR into the beta CD cavity,
and depending on the generation, different preorganization scenarios
were promoted before complex-ation. Phase solubility diagrams showed
that all the dendronized containers have superior performance for
solubilizing CUR compared to native beta CD. We proved that
coprecipitation is most efficient than lyophilization for forming
inclusion complexes (ICs) with dendronized containers. Even though beta
CD-3G with the largest 3G dendron exhibited the highest CUR loading, the
complexation of CUR with beta CD-2G provided the supramolecular system
that contains CUR preferentially in its diketo tautomer, which is known
for its antioxidant activity.
Filiaciones:
Citlali Cabrera-Quinones, Neyra:
Univ Nacl Autonoma Mexico, Inst Invest Mat, Lab Mat Supramol SupraMatLab, Mexico City 04510, DF, Mexico
Jose Lopez-Mendez, Luis:
Univ Nacl Autonoma Mexico, Inst Invest Mat, Lab Mat Supramol SupraMatLab, Mexico City 04510, DF, Mexico
Ramos, Estrella:
Univ Nacl Autonoma Mexico, Inst Invest Mat, Mexico City 04510, DF, Mexico
Rojas-Aguirre, Yareli:
Univ Nacl Autonoma Mexico, Inst Invest Mat, Lab Mat Supramol SupraMatLab, Mexico City 04510, DF, Mexico
GUADARRAMA, PATRICIA:
Univ Nacl Autonoma Mexico, Inst Invest Mat, Lab Mat Supramol SupraMatLab, Mexico City 04510, DF, Mexico
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