Non-covalent inclusion of ferulic acid with alpha-cyclodextrin improves photo-stability and delivery: NMR and modeling studies

Journal of Pharmaceutical and Biomedical Analysis
Cecilia AnselmiRoberto Maffei Facino

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 for cosmetic application because of its low physicochemical stability. We prepared the inclusion complex of FA with alpha-cyclodextrin by co-precipitation from an aqueous solution, and used (1)H NMR and molecular dynamics to investigate the most probable structure of the inclusion complex. In rotating frame nuclear Overhouser effect spectroscopy (ROESY) experiments FA penetrated the alpha-CD hydrophobic cavity with the alpha,beta-unsaturated part of the molecule and some of its aromatic skeleton. In proton chemical shift measurements of FA and alpha-cyclodextrins we determined the stoichiometry of the association complex (1:1) by Job's method, and its stability constant (K(1:1) 1162+/-140 M(-1)) and described the molecular dynamics of the complex on the basis of theoretical studies. Encapsulation with alpha-cyclodextrin improves (i) the chemical stability of FA against UVB stress (10 MED [Minimal Erythemal Dose: 1 MED=25 mJ/cm(2) 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...Continue Reading

References

Nov 21, 2001·Journal of Agricultural and Food Chemistry·M F Maggi-CapeyronB Descomps
Mar 21, 2002·Journal of Agricultural and Food Chemistry·Hiroe KikuzakiHisaji Taniguchi
Nov 8, 2003·Acta Diabetologica·M Sri BalasubashiniV P Menon

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Citations

Jul 25, 2008·Biogerontology·Eugenio BaroneCesare Mancuso
Mar 30, 2013·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Hanane MessiadOmar Houache
Feb 18, 2016·Journal of Pharmaceutical Sciences·Carolina AloisioMarcela Longhi
Aug 18, 2010·International Journal of Pharmaceutics·Deng-Guang YuLi-Min Zhu
Jan 8, 2015·International Journal of Cosmetic Science·D MontiC Anselmi
Dec 5, 2013·Carbohydrate Polymers·Eva PinhoMariana Henriques
May 24, 2014·Pharmaceutical Development and Technology·Marisanna CentiniCecilia Anselmi
May 9, 2015·Food Chemistry·Gortzi OlgaRoussis G Ioannis
Aug 19, 2014·Journal of Pharmaceutical and Biomedical Analysis·Carolina AloisioMarcela Longhi
Apr 30, 2016·Materials Science & Engineering. C, Materials for Biological Applications·Jessica Mendes NadalSandra Maria Warumby Zanin
Jan 1, 2011·Pharmaceutics·Aude Munin, Florence Edwards-Lévy
Feb 6, 2019·International Journal of Molecular Sciences·Simone Braga CarneiroÁdley Antonini Neves de Lima
Oct 10, 2014·Beilstein Journal of Organic Chemistry·Miriana KfourySophie Fourmentin
Oct 18, 2019·Journal of Nutritional Science and Vitaminology·Cecilia AnselmiAnna Buonocore
Apr 18, 2018·Environmental Science and Pollution Research International·Mengbi WeiHuihui Liu
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Layan DahabraMouhamad Khoder
Aug 8, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Julia A H KaeswurmMaria Buchweitz

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