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Esters of terpene alcohols as highly potent, reversible, and low toxic skin penetration enhancers
M. Kopečná, M. Macháček, A. Nováčková, G. Paraskevopoulos, J. Roh, K. Vávrová,
Jazyk angličtina Země Velká Británie
Typ dokumentu časopisecké články, práce podpořená grantem
NLK
Directory of Open Access Journals
od 2011
Free Medical Journals
od 2011
PubMed Central
od 2011
Europe PubMed Central
od 2011
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od 2011-01-01 do 2019-12-31
Open Access Digital Library
od 2011-01-01
Open Access Digital Library
od 2011-01-01
Health & Medicine (ProQuest)
od 2011-01-01 do 2019-12-31
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- MeSH
- alkoholy chemie farmakologie MeSH
- aplikace kožní MeSH
- buňky 3T3 MeSH
- cidofovir aplikace a dávkování chemie farmakokinetika MeSH
- epidermis účinky léků metabolismus MeSH
- estery chemie farmakologie MeSH
- farmaceutická chemie MeSH
- farmaceutické pomocné látky chemie farmakologie MeSH
- hydrokortison aplikace a dávkování chemie farmakokinetika MeSH
- keratinocyty MeSH
- lidé MeSH
- metabolismus lipidů účinky léků MeSH
- monoterpeny chemie MeSH
- myši MeSH
- permeabilita účinky léků MeSH
- perspiratio insensibilis účinky léků MeSH
- příprava léků metody MeSH
- terpeny chemie farmakologie MeSH
- testy akutní toxicity MeSH
- theofylin aplikace a dávkování chemie farmakokinetika MeSH
- vztahy mezi strukturou a aktivitou MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Skin penetration/permeation enhancers are compounds that improve (trans)dermal drug delivery. We designed hybrid terpene-amino acid enhancers by conjugating natural terpenes (citronellol, geraniol, nerol, farnesol, linalool, perillyl alcohol, menthol, borneol, carveol) or cinnamyl alcohol with 6-(dimethylamino)hexanoic acid through a biodegradable ester linker. The compounds were screened for their ability to increase the delivery of theophylline and hydrocortisone through and into human skin ex vivo. The citronellyl, bornyl and cinnamyl esters showed exceptional permeation-enhancing properties (enhancement ratios up to 82) while having low cellular toxicities. The barrier function of enhancer-treated skin (assessed by transepidermal water loss and electrical impedance) recovered within 24 h. Infrared spectroscopy suggested that these esters fluidized the stratum corneum lipids. Furthermore, the citronellyl ester increased the epidermal concentration of topically applied cidofovir, which is a potent antiviral and anticancer drug, by 15-fold. In conclusion, citronellyl 6-(dimethylamino)hexanoate is an outstanding enhancer with an advantageous combination of properties, which may improve the delivery of drugs that have a limited ability to cross biological barriers.
Citace poskytuje Crossref.org
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- $a Kopečná, Monika $u Skin Barrier Research Group, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
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- $a Skin penetration/permeation enhancers are compounds that improve (trans)dermal drug delivery. We designed hybrid terpene-amino acid enhancers by conjugating natural terpenes (citronellol, geraniol, nerol, farnesol, linalool, perillyl alcohol, menthol, borneol, carveol) or cinnamyl alcohol with 6-(dimethylamino)hexanoic acid through a biodegradable ester linker. The compounds were screened for their ability to increase the delivery of theophylline and hydrocortisone through and into human skin ex vivo. The citronellyl, bornyl and cinnamyl esters showed exceptional permeation-enhancing properties (enhancement ratios up to 82) while having low cellular toxicities. The barrier function of enhancer-treated skin (assessed by transepidermal water loss and electrical impedance) recovered within 24 h. Infrared spectroscopy suggested that these esters fluidized the stratum corneum lipids. Furthermore, the citronellyl ester increased the epidermal concentration of topically applied cidofovir, which is a potent antiviral and anticancer drug, by 15-fold. In conclusion, citronellyl 6-(dimethylamino)hexanoate is an outstanding enhancer with an advantageous combination of properties, which may improve the delivery of drugs that have a limited ability to cross biological barriers.
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- $a Roh, Jaroslav $u Department of Organic and Bioorganic Chemistry, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
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