Dodecyl Amino Glucoside Enhances Transdermal and Topical Drug Delivery via Reversible Interaction with Skin Barrier Lipids
Language English Country United States Media print-electronic
Document type Journal Article
PubMed
28070753
DOI
10.1007/s11095-016-2093-z
PII: 10.1007/s11095-016-2093-z
Knihovny.cz E-resources
- Keywords
- penetration enhancers, sugar, topical drug delivery, transdermal drug delivery,
- MeSH
- Antiviral Agents administration & dosage metabolism MeSH
- Administration, Cutaneous MeSH
- Administration, Topical MeSH
- Cell Line MeSH
- Chemistry, Pharmaceutical MeSH
- Cidofovir MeSH
- Cytosine administration & dosage analogs & derivatives metabolism MeSH
- Epidermis drug effects metabolism MeSH
- Glucosides chemical synthesis pharmacology MeSH
- Hexoses pharmacology MeSH
- Hydrophobic and Hydrophilic Interactions MeSH
- Keratinocytes drug effects metabolism MeSH
- Skin Absorption MeSH
- Skin drug effects metabolism MeSH
- Humans MeSH
- Lipids physiology MeSH
- Organophosphonates administration & dosage metabolism MeSH
- Permeability MeSH
- Drug Delivery Systems MeSH
- Theophylline administration & dosage metabolism MeSH
- Cell Survival MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Antiviral Agents MeSH
- Cidofovir MeSH
- Cytosine MeSH
- Glucosides MeSH
- Hexoses MeSH
- Lipids MeSH
- Organophosphonates MeSH
- sorbitan monolaurate MeSH Browser
- Theophylline 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.
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