Physical properties and biological activities of hesperetin and naringenin in complex with methylated ?-cyclodextrin.

ABSTRACT: The aim of this work is to improve physical properties and biological activities of the two flavanones hesperetin and naringenin by complexation with ?-cyclodextrin (?-CD) and its methylated derivatives (2,6-di-O-methyl-?-cyclodextrin, DM-?-CD and randomly methylated-?-CD, RAMEB). The free energies of inclusion complexes between hesperetin with cyclodextrins (?-CD and DM-?-CD) were theoretically investigated by molecular dynamics simulation. The free energy values obtained suggested a more stable inclusion complex with DM-?-CD. The vdW force is the main guest-host interaction when hesperetin binds with CDs. The phase solubility diagram showed the formation of a soluble complex of AL type, with higher increase in solubility and stability when hesperetin and naringenin were complexed with RAMEB. Solid complexes were prepared by freeze-drying, and the data from differential scanning calorimetry (DSC) confirmed the formation of inclusion complexes. The data obtained by the dissolution method showed that complexation with RAMEB resulted in a better release of both flavanones to aqueous solution. The flavanones-?-CD/DM-?-CD complexes demonstrated a similar or a slight increase in anti-inflammatory activity and cytotoxicity towards three different cancer cell lines. The overall results suggested that solubilities and bioactivities of both flavanones were increased by complexation with methylated ?-CDs.

SUBMITTER: Sangpheak W 

PROVIDER: S-EPMC4734351 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature