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Oleate-modified hyaluronan: Controlling the number and distribution of side chains by varying the reaction conditions
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SYSNO ASEP 0543196 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Oleate-modified hyaluronan: Controlling the number and distribution of side chains by varying the reaction conditions Author(s) Štrympl, O. (CZ)
Vohlídal, J. (CZ)
Hermannová, M. (CZ)
Maldonado-Domínguez, Mauricio (UFCH-W) ORCID
Brandejsová, M. (CZ)
Kopecká, K. (CZ)
Velebný, V. (CZ)
Huerta-Ángeles, G. (CZ)Article number 118197 Source Title Carbohydrate Polymers. - : Elsevier - ISSN 0144-8617
Roč. 267, SEP2021 (2021)Number of pages 10 s. Language eng - English Country GB - United Kingdom 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 Subject RIV CF - Physical ; Theoretical Chemistry OECD category Physical chemistry Method of publishing Limited access Institutional support UFCH-W - RVO:61388955 UT WOS 000694014300008 EID SCOPUS 85107071968 DOI 10.1016/j.carbpol.2021.118197 Annotation 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. Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2022 Electronic address http://hdl.handle.net/11104/0320467
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