Synthesis of novel amphiphilic hyaluronan containing-aromatic fatty acids for fabrication of polymeric micelles

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F16%3A39915942" target="_blank" >RIV/00216275:25310/16:39915942 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/70883521:28110/16:43874585

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/abs/pii/S0144861716307603" target="_blank" >https://www.sciencedirect.com/science/article/abs/pii/S0144861716307603</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.carbpol.2016.06.085" target="_blank" >10.1016/j.carbpol.2016.06.085</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of novel amphiphilic hyaluronan containing-aromatic fatty acids for fabrication of polymeric micelles

Popis výsledku v původním jazyce

Novel hydrophobized hyaluronan (HA) derivatives, containing omega-phenylalkanoic acids (omega-PAA, 4-phenylbutyric acid, 6-phenylhexanoic, 8-phenyloctanoic or 11-tolylundecanoic acids) were prepared by esterification. Mixed anhydrides obtained after reaction of the carboxyl acid moiety and benzoyl chloride were found to be active acylating agents, affording hydrophobized HA in good yield and under mild conditions. The reactivity of the aromatic fatty acids towards esterification has decreased with the increasing length of the aliphatic spacer between the aromatic substituent and carboxylic acid moiety. The novel HA derivatives self-assembled from very low concentrations and were found to be non-cytotoxic. The potential use of omega-phenylalkanoic acids grafted-HA towards drug delivery applications was demonstrated by hydrophobic drugs (resveratrol and retinyl palmitate) encapsulation. The drug loading capacity of the novel HA derivatives was significantly improved most likely because of pi center dot center dot center dot pi interactions between the micelle core and loaded hydrophobic aromatic compound.

Název v anglickém jazyce

Synthesis of novel amphiphilic hyaluronan containing-aromatic fatty acids for fabrication of polymeric micelles

Popis výsledku anglicky

Novel hydrophobized hyaluronan (HA) derivatives, containing omega-phenylalkanoic acids (omega-PAA, 4-phenylbutyric acid, 6-phenylhexanoic, 8-phenyloctanoic or 11-tolylundecanoic acids) were prepared by esterification. Mixed anhydrides obtained after reaction of the carboxyl acid moiety and benzoyl chloride were found to be active acylating agents, affording hydrophobized HA in good yield and under mild conditions. The reactivity of the aromatic fatty acids towards esterification has decreased with the increasing length of the aliphatic spacer between the aromatic substituent and carboxylic acid moiety. The novel HA derivatives self-assembled from very low concentrations and were found to be non-cytotoxic. The potential use of omega-phenylalkanoic acids grafted-HA towards drug delivery applications was demonstrated by hydrophobic drugs (resveratrol and retinyl palmitate) encapsulation. The drug loading capacity of the novel HA derivatives was significantly improved most likely because of pi center dot center dot center dot pi interactions between the micelle core and loaded hydrophobic aromatic compound.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

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

—

Svazek periodika

151

Číslo periodika v rámci svazku

October

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

"1175–1183"

Kód UT WoS článku

000380943900132

EID výsledku v databázi Scopus

2-s2.0-84978042707