| Synthesis, hydrolysis, and skin retention of amino acid esters of alpha-tocopherol. | |
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MedLine Citation:
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PMID: 18973192 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The aim of this work was to synthesize new pro-vitamins of alpha-tocopherol (VE) able to release another moiety such as an amino acid, in order to obtain a combined antioxidant and moisturizing effect upon topical application. The new derivatives were characterized and tested for sensitivity to chemical and enzymatic hydrolysis. Lipophilicity was estimated using Log capacity factor and skin retention was determined in vitro, using rabbit ear skin as barrier. Five molecules were synthesized using L-proline, L-serine, L-tyrosine, L-asparagine, and L-citrulline as amino acidic moiety. All pro-vitamins showed similar or lower lipophilicity than alpha-tocopheryl acetate (VEAc), taken as reference, and similar stability in aqueous solutions. All pro-vitamins showed to be sensitive to enzymatic hydrolysis. None of the pro-vitamins crossed the skin in significant amounts, whereas they accumulated into the skin, in both the dermis and the epidermis. They are more hydrophilic and more water-soluble than the currently used acetate. |
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Authors:
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Fabio Marra; Carmine Ostacolo; Sonia Laneri; Antonietta Bernardi; Antonia Sacchi; Cristina Padula; Sara Nicoli; Patrizia Santi |
Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of pharmaceutical sciences Volume: 98 ISSN: 1520-6017 ISO Abbreviation: J Pharm Sci Publication Date: 2009 Jul |
Date Detail:
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Created Date: 2009-06-02 Completed Date: 2009-08-19 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985195R Medline TA: J Pharm Sci Country: United States |
Other Details:
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Languages: eng Pagination: 2364-76 Citation Subset: IM |
Affiliation:
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Dipartimento Farmaceutico, University of Parma, Viale G.P. Usberti 27/A, 43100 Parma, Italy. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis*,
chemistry Animals Antioxidants / chemical synthesis, chemistry, metabolism Esterases / metabolism Hydrolysis Lipids / chemistry Liver / enzymology Rabbits Skin / metabolism* Skin Absorption Solubility Swine Vitamin E / analogs & derivatives, chemical synthesis*, chemistry, metabolism* alpha-Tocopherol / analogs & derivatives, chemical synthesis*, chemistry, metabolism* |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Antioxidants; 0/Lipids; 1406-18-4/Vitamin E; 59-02-9/alpha-Tocopherol; EC 3.1.-/Esterases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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