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|Title:||Non-covalent inclusion of ferulic acid with alpha-cyclodextrin improves photo-stability and delivery: NMR and modeling studies||Authors:||Anselmi, Cecilia
MAFFEI FACINO, R.
|Keywords:||Ferulic acid; alpha-cyclodextrin; Inclusion complex; NMR; Molecular modeling; Photostability; Antioxidant activity; Delivery||Issue Date:||2008||Project:||None||Journal:||JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS||Abstract:||
Ferulic acid (FA) is a highly effective antioxidant and photo-protective agent, already approved in Japan as a sunscreen, but it is poorly suited forcosmetic application because of its low physicochemical stability.We prepared the inclusion complex of FA with -cyclodextrin by co-precipitationfrom an aqueous solution, and used 1HNMRand molecular dynamics to investigate the most probable structure of the inclusion complex. In rotatingframe nuclear Overhouser effect spectroscopy (ROESY) experiments FA penetrated the -CD hydrophobic cavity with the ,-unsaturated part ofthe molecule and some of its aromatic skeleton. In proton chemical shift measurements of FA and -cyclodextrins we determined the stoichiometryof the association complex (1:1) by Job’s method, and its stability constant (K1:1 1162±140M−1) and described the molecular dynamics of thecomplex on the basis of theoretical studies. Encapsulation with -cyclodextrin improves (i) the chemical stability of FA against UVB stress (10MED [Minimal Erythemal Dose: 1 MED= 25 mJ/cm2 for skin phototype II: 30]), since no degradation products are formed after irradiation, and(ii) the bioavailability of FA on the skin, slowing its delivery (Strainer cell model).
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