Synthesis and self-assembling of hyaluronan grafted with ceramide NP for topical drug delivery

0575039 - ÚMCH 2024 RIV NL eng J - Článek v odborném periodiku
Juhaščik, M. - Štarmanová, K. - Brandejsová, M. - Večeřová, P. - Hermannová, M. - Exnerová, A. - Vagnerová, H. - Štrympl, O. - Nešporová, K. - Kováčik, A. - Velebný, V. - Huerta-Ángeles, Gloria
Synthesis and self-assembling of hyaluronan grafted with ceramide NP for topical drug delivery.
Carbohydrate Polymers. Roč. 321, 1 December (2023), č. článku 121283. ISSN 0144-8617. E-ISSN 1879-1344
Institucionální podpora: RVO:61389013
Klíčová slova: ceramides * hyaluronan * skin penetration
Obor OECD: Polymer science
Impakt faktor: 11.2, rok: 2022
Způsob publikování: Omezený přístup
https://www.sciencedirect.com/science/article/pii/S0144861723007488?via%3Dihub

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.
Trvalý link: https://hdl.handle.net/11104/0345061