Oleate-modified hyaluronan: Controlling the number and distribution of side chains by varying the reaction conditions

0543196 - ÚFCH JH 2022 RIV GB eng J - Journal Article
Štrympl, O. - Vohlídal, J. - Hermannová, M. - Maldonado-Domínguez, Mauricio - Brandejsová, M. - Kopecká, K. - Velebný, V. - Huerta-Ángeles, G.
Oleate-modified hyaluronan: Controlling the number and distribution of side chains by varying the reaction conditions.
Carbohydrate Polymers. Roč. 267, SEP2021 (2021), č. článku 118197. ISSN 0144-8617. E-ISSN 1879-1344
Institutional support: RVO:61388955
Keywords : Amphiphiles * Hyaluronan * Mixed anhydrides * Oleic acid (PubChem CID: 445639) * Pyrene (PubChem CID: 31423) * Self-assembly * Sodium hyaluronate (PubChem CID: 53447380) * Solvent effect * Substituent distribution pattern
OECD category: Physical chemistry
Impact factor: 10.723, year: 2021
Method of publishing: Limited access

In this work, low molecular weight hyaluronan was chemically modified by oleoyl moieties utilising mixed anhydrides methodology. The activation of oleic acid with benzoyl chloride in organic solvents miscible with water was followed by NMR spectroscopy. The product selectivity correlates with the solvent's Hildebrand solubility parameter. Furthermore, the effect of the solvent for the mixed anhydride formation was elucidated by density functional theory (DFT) and showed that the reactions are faster in acetonitrile or alcohols than in hexane. Furthermore, the solvent demonstrated to control the substituent distribution pattern along HA chain during esterification. An even distribution of substituents was observed in reactions performed in water mixed with ethers. The substituent distribution pattern clearly influenced the aggregation behaviour of amphiphilic HA, controlling the stability of the delivery system, while increasing the encapsulation capacity.
Permanent Link: http://hdl.handle.net/11104/0320467