Evaluation of salicylic acid fatty ester prodrugs for UV protection

Autor:	Eun Mi Jeon, Prabagar Balakrishnan, Dae-Duk Kim, Dong Hoon Oh, Jong Seob Im, Jungsun Kim, Chul Soon Yong, Han-Gon Choi
Rok vydání:	2011
Předmět:	Ultraviolet Rays Skin Absorption Drug Evaluation Preclinical Pharmaceutical Science In Vitro Techniques Mice chemistry.chemical_compound Hydrolysis Drug Stability Enzymatic hydrolysis Drug Discovery Stratum corneum medicine Animals Organic chemistry Prodrugs Skin Pharmacology Mice Hairless Ethanol Chromatography integumentary system Fatty Acids Organic Chemistry Permeation Prodrug Salicylates medicine.anatomical_structure chemistry Lipophilicity Sunscreening Agents Salicylic acid
Zdroj:	Drug Development and Industrial Pharmacy. 37:841-848
ISSN:	1520-5762 0363-9045
DOI:	10.3109/03639045.2010.545417
Popis:	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.
Databáze:	OpenAIRE
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