Evaluation of salicylic acid fatty ester prodrugs for UV protection

Title
Evaluation of salicylic acid fatty ester prodrugs for UV protection
Author(s)
용철순입종섭[입종섭]프라바가[프라바가]오동훈[오동훈]김정선[김정선]전은미[전은미]김대덕[김대덕]최한곤[최한곤]
Keywords
NONSTEROIDAL ANTIINFLAMMATORY DRUGS; PERMEABILITY BARRIER FUNCTION; SKIN PERMEATION ENHANCEMENT; TRANSDERMAL DELIVERY; IN-VITRO; PERCUTANEOUS-ABSORPTION; PENETRATION ENHANCERS; ALCOHOLS; INVITRO
Issue Date
201101
Publisher
INFORMA HEALTHCARE
Citation
DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY, v.37, no.7, pp.841 - 848
Abstract
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.</.
URI
http://hdl.handle.net/YU.REPOSITORY/25731http://dx.doi.org/10.3109/03639045.2010.545417
ISSN
0363-9045
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약학대학 > 약학부 > Articles
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