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Influence of hydroxypropyl-β-cyclodextrin on the photostability and antiradical activity of Trolox

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Abstract

Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), a derivative of vitamin E, can undergo photolysis upon UV irradiation. In the present study the photodegradation kinetics of Trolox were thus investigated in different systems in the absence and in the presence of titanium dioxide, a physical sunscreen present in several cosmetic products, that can act as photocatalyst. In all the considered media Trolox degraded under UVB light following pseudo-zero order kinetics, probably by a mechanism of photooxidation. The rate of Trolox photodegradation was lower in O/W emulsions than in aqueous solution and in gel; furthermore it was significantly influenced by the presence of TiO2. Aiming to increase Trolox stability, it was complexed with hydroxypropyl-β-cyclodextrin: the inclusion complex was characterized by phase solubility studies, spectrophotometry and differential scanning calorimetry. The irradiation experiments indicated that complexation with hydroxypropyl-β-cyclodextrin was effective in reducing the photodegradation rate of Trolox. Moreover the host molecule favored the uptake of Trolox into the porcine skin, as shown by in vitro permeation studies. Nevertheless the assay of peroxidation, based on the reaction of malondialdehyde with thiobarbituric acid, indicated that the antioxidant activity of Trolox was maintained even after inclusion in cyclodextrin.

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Authors and Affiliations

  1. Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, via P.Giuria 9, 10125, Torino, Italy

    M. E. Carlotti, S. Sapino, S. Marino, E. Ugazio, D. Chirio & R. Cavalli

  2. Dipartimento di Chimica IFM, Università degli Studi di Torino, via P.Giuria 7, 10125, Torino, Italy

    F. Trotta

  3. Dipartimento di Chimica Analitica, Università degli Studi di Torino, via P.Giuria 5, 10125, Torino, Italy

    D. Vione

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  1. M. E. Carlotti
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  2. S. Sapino
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  3. S. Marino
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  4. E. Ugazio
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  5. F. Trotta
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  6. D. Vione
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  7. D. Chirio
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  8. R. Cavalli
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Correspondence to M. E. Carlotti.

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Carlotti, M.E., Sapino, S., Marino, S. et al. Influence of hydroxypropyl-β-cyclodextrin on the photostability and antiradical activity of Trolox. J Incl Phenom Macrocycl Chem 61, 279–287 (2008). https://doi.org/10.1007/s10847-008-9420-x

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  • DOI: https://doi.org/10.1007/s10847-008-9420-x

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