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Dodecyl Amino Glucoside Enhances Transdermal and Topical Drug Delivery via Reversible Interaction with Skin Barrier Lipids
M. Kopečná, M. Macháček, E. Prchalová, P. Štěpánek, P. Drašar, M. Kotora, K. Vávrová,
Jazyk angličtina Země Spojené státy americké
Typ dokumentu časopisecké články
NLK
ProQuest Central
od 1997-01-01 do Před 1 rokem
Medline Complete (EBSCOhost)
od 2010-01-01 do Před 1 rokem
Nursing & Allied Health Database (ProQuest)
od 1997-01-01 do Před 1 rokem
Health & Medicine (ProQuest)
od 1997-01-01 do Před 1 rokem
- MeSH
- antivirové látky aplikace a dávkování metabolismus MeSH
- aplikace kožní MeSH
- aplikace lokální MeSH
- buněčné linie MeSH
- cytosin aplikace a dávkování analogy a deriváty metabolismus MeSH
- epidermis účinky léků metabolismus MeSH
- farmaceutická chemie MeSH
- glukosidy chemická syntéza farmakologie MeSH
- hexosy farmakologie MeSH
- hydrofobní a hydrofilní interakce MeSH
- keratinocyty účinky léků metabolismus MeSH
- kožní absorpce MeSH
- kůže účinky léků metabolismus MeSH
- lékové transportní systémy MeSH
- lidé MeSH
- lipidy fyziologie MeSH
- organofosfonáty aplikace a dávkování metabolismus MeSH
- permeabilita MeSH
- theofylin aplikace a dávkování metabolismus MeSH
- viabilita buněk MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
PURPOSE: Skin permeation/penetration enhancers are substances that enable drug delivery through or into the skin. METHODS: To search for new enhancers with high but reversible activity and acceptable toxicity, we synthesized a series of D-glucose derivatives, both hydrophilic and amphiphilic. RESULTS: Initial evaluation of the ability of these sugar derivatives to increase permeation and penetration of theophylline through/into human skin compared with a control (no enhancer) or sorbitan monolaurate (Span 20; positive control) revealed dodecyl 6-amino-6-deoxy-α-D-glucopyranoside 5 as a promising enhancer. Furthermore, this amino sugar 5 increased epidermal concentration of a highly hydrophilic antiviral cidofovir by a factor of 7. The effect of compound 5 on skin electrical impedance suggested its direct interaction with the skin barrier. Infrared spectroscopy of isolated stratum corneum revealed no effect of enhancer 5 on the stratum corneum proteins but an overall decrease in the lipid chain order. The enhancer showed acceptable toxicity on HaCaT keratinocyte and 3T3 fibroblast cell lines. Finally, transepidermal water loss returned to baseline values after enhancer 5 had been removed from the skin. CONCLUSIONS: Compound 5, a dodecyl amino glucoside, is a promising enhancer that acts through a reversible interaction with the stratum corneum lipids.
Citace poskytuje Crossref.org
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- $a Kopečná, Monika $u Skin Barrier Research Group, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
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- $a Dodecyl Amino Glucoside Enhances Transdermal and Topical Drug Delivery via Reversible Interaction with Skin Barrier Lipids / $c M. Kopečná, M. Macháček, E. Prchalová, P. Štěpánek, P. Drašar, M. Kotora, K. Vávrová,
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- $a PURPOSE: Skin permeation/penetration enhancers are substances that enable drug delivery through or into the skin. METHODS: To search for new enhancers with high but reversible activity and acceptable toxicity, we synthesized a series of D-glucose derivatives, both hydrophilic and amphiphilic. RESULTS: Initial evaluation of the ability of these sugar derivatives to increase permeation and penetration of theophylline through/into human skin compared with a control (no enhancer) or sorbitan monolaurate (Span 20; positive control) revealed dodecyl 6-amino-6-deoxy-α-D-glucopyranoside 5 as a promising enhancer. Furthermore, this amino sugar 5 increased epidermal concentration of a highly hydrophilic antiviral cidofovir by a factor of 7. The effect of compound 5 on skin electrical impedance suggested its direct interaction with the skin barrier. Infrared spectroscopy of isolated stratum corneum revealed no effect of enhancer 5 on the stratum corneum proteins but an overall decrease in the lipid chain order. The enhancer showed acceptable toxicity on HaCaT keratinocyte and 3T3 fibroblast cell lines. Finally, transepidermal water loss returned to baseline values after enhancer 5 had been removed from the skin. CONCLUSIONS: Compound 5, a dodecyl amino glucoside, is a promising enhancer that acts through a reversible interaction with the stratum corneum lipids.
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- $a Macháček, Miloslav $u Department of Biochemical Sciences, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
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- $a Prchalová, Eva $u Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo náměstí 2, 166 10, Praha 6, Czech Republic.
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- $a Štěpánek, Petr $u Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Technická 5, 166 28, Praha 6, Dejvice, Czech Republic.
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- $a Kotora, Martin $u Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo náměstí 2, 166 10, Praha 6, Czech Republic. Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 123 43, Praha 2, Czech Republic.
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- $a Vávrová, Kateřina $u Skin Barrier Research Group, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic. katerina.vavrova@faf.cuni.cz.
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