| Evaluation of salicylic acid fatty ester prodrugs for UV protection. | |
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MedLine Citation:
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PMID: 21244220 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The purpose of this study was to investigate the physicochemical properties and in vitro evaluation of fatty ester prodrugs of salicylic acid for ultraviolet (UV) protection. The physicochemical properties such as lipophilicity, chemical stability and enzymatic hydrolysis were investigated with the following fatty ester prodrugs of salicylic acid: octanoyl (C8SA), nonanoyl (C9SA), decanoyl (C10SA), lauroyl (C12SA), myristoyl (C14SA) and palmitoyl oxysalicylate (C16SA). Furthermore, their skin permeation and accumulation were evaluated using a combination of common permeation enhancing techniques such as the use of a lipophilic receptor solution, removal of stratum corneum and delipidization of skin. Their k' values were proportional to the degree of carbon-carbon saturation in the side chain. All these fatty esters were highly stable in 2-propanol, acetonitrile and glycerin, but unstable in methanol and ethanol. They were relatively unstable in liver and skin homogenates. In particular, C16SA was mostly hydrolyzed to its parent compound in hairless mouse liver and skin homogenates, suggesting that it might be converted to salicylic acid after its topical administration. In the skin permeation and accumulation study, C16SA showed the poorest permeation in all skins, suggesting that it could not be permeated in the skin. Furthermore, C14SA and C16SA were less accumulated in delipidized skin compared with normal skin or stripped skin, suggesting that these esters had relatively strong affinities for lipids compared with the other prodrugs in the skin. C16SA showed significantly higher dermal accumulation in all skins compared with its parent salicylic acid. Thus, the palmitoyl oxysalicylate (C16SA) might be a potential candidate for UV protection due to its absence of skin permeation, smaller uptake in the lipid phase and relatively lower skin accumulation. |
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Authors:
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Jong Seob Im; Prabagar Balakrishnan; Dong Hoon Oh; Jung Sun Kim; Eun-Mi Jeon; Dae-Duk Kim; Chul Soon Yong; Han-Gon Choi |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-1-18 |
Journal Detail:
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Title: Drug development and industrial pharmacy Volume: - ISSN: 1520-5762 ISO Abbreviation: - Publication Date: 2011 Jan |
Date Detail:
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Created Date: 2011-1-19 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7802620 Medline TA: Drug Dev Ind Pharm Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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College of Pharmacy, Yeungnam University, Dae-Dong, Gyongsan, South Korea. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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