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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F21%3A00543196" target="_blank" >RIV/61388955:_____/21:00543196 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/21:10431416

Výsledek na webu

<a href="http://hdl.handle.net/11104/0320467" target="_blank" >http://hdl.handle.net/11104/0320467</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.carbpol.2021.118197" target="_blank" >10.1016/j.carbpol.2021.118197</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Carbohydrate Polymers

ISSN

0144-8617

e-ISSN

1879-1344

Svazek periodika

267

Číslo periodika v rámci svazku

SEP2021

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

118197

Kód UT WoS článku

000694014300008

EID výsledku v databázi Scopus

2-s2.0-85107071968