Synthesis and self-assembling of hyaluronan grafted with ceramide NP for topical drug delivery
Language English Country England, Great Britain Media print-electronic
Document type Journal Article
PubMed
37739524
DOI
10.1016/j.carbpol.2023.121283
PII: S0144-8617(23)00748-8
Knihovny.cz E-resources
- Keywords
- Amphiphilic polysaccharides, Ceramides, Hyaluronan, IL-6, Self-assembling, Skin penetration,
- MeSH
- Ceramides MeSH
- Esterification MeSH
- Hyaluronic Acid * MeSH
- Drug Delivery Systems * MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Ceramides MeSH
- Hyaluronic Acid * MeSH
- phytosphingosine MeSH Browser
In this work, amphiphilic hyaluronan was synthesized by grafting succinylated N-oleoyl-phytosphingosine via esters bonds. Succinylated N-oleoyl-phytosphingosine (sCER) was first prepared by esterification of hydroxyl moieties of the ceramide with succinic anhydride. The esterification of hyaluronan was governed by crowding effect. The oligomeric HA-sCER derivatives exhibited a strong self-aggregation as evidenced by a very low critical aggregation concentration (1.9 μg mL-1), higher pyrene binding constant (KB), and the smallest particle size (30 nm) in solution. The self-aggregation properties demonstrated to be a function of the substitution degree and molecular weight of HA. The prepared derivatives were non-cytotoxic towards cell lines NIH-3T3. Nanoparticles prepared using oligomeric HA-sCER derivatives improved the penetration of Nile red dye through the stratum corneum due to their smaller size (≤50 nm). The fluorescence intensity localized at the stratum corneum was higher for oligomeric HA-sCER. A significant inhibition of the pro-inflammatory cytokine interleukin-6 production was observed in vitro in macrophages differentiated from THP-1 cells. These findings showed that HA-sCER constituted a promising active ingredient for cosmetics use.
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