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

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dc.title Synthesis of novel amphiphilic hyaluronan containing-aromatic fatty acids for fabrication of polymeric micelles en
dc.contributor.author Matelová, Alena
dc.contributor.author Huerta-Angeles, Gloria
dc.contributor.author Šmejkalová, Daniela
dc.contributor.author Brůnová, Zdislava
dc.contributor.author Dušek, Jan
dc.contributor.author Vícha, Robert
dc.contributor.author Velebný, Vladimír
dc.relation.ispartof Carbohydrate Polymers
dc.identifier.issn 0144-8617 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2016
utb.relation.volume 151
dc.citation.spage 1175
dc.citation.epage 1183
dc.type article
dc.language.iso en
dc.publisher Pergamon Elsevier Science Ltd.
dc.identifier.doi 10.1016/j.carbpol.2016.06.085
dc.relation.uri https://www.sciencedirect.com/science/article/pii/S0144861716307603
dc.subject Amphiphilic polysaccharides en
dc.subject Hyaluronic acid en
dc.subject Topical application en
dc.subject ω-Phenylalkanoic acids en
dc.description.abstract Novel hydrophobized hyaluronan (HA) derivatives, containing ω-phenylalkanoic acids (ω-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 ω-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 π⋯π interactions between the micelle core and loaded hydrophobic aromatic compound. © 2016 Elsevier Ltd en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1006569
utb.identifier.obdid 43875210
utb.identifier.scopus 2-s2.0-84978042707
utb.identifier.wok 000380943900132
utb.identifier.pubmed 27474668
utb.identifier.coden CAPOD
utb.source j-scopus
dc.date.accessioned 2016-09-21T13:12:19Z
dc.date.available 2016-09-21T13:12:19Z
dc.description.sponsorship Tomas Bata University in Zlin [IGA/FT/2016/001]; program "Institute CONTIPRO"; Ministry of Education, Youth and Sports of the Czech Republic
utb.contributor.internalauthor Matelová, Alena
utb.contributor.internalauthor Vícha, Robert
utb.fulltext.affiliation Alena Matelová a,b, Gloria Huerta-Angeles a∗, Daniela Šmejkalová a, Zdislava Brůnová a, Jan Dušek c, Robert Vícha b, Vladimír Velebný a a Contipro a.s., Dolní Dobrouč 401, 561 02 Dolní Dobrouč, Czech Republic b Department of Chemistry, Faculty of Technology, Tomáš Bat’a University in Zlín, Vavrečkova 275, 760 01 Zlín, Czech Republic c Institute of Organic Chemistry and Technology, Faculty of Chemical Technology University Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic ∗ Corresponding author. E-mail address: huerta-angeles@contipro.com (G. Huerta-Angeles).
utb.fulltext.dates Received 11 May 2016 Received in revised form 19 June 2016 Accepted 20 June 2016 Available online 21 June 2016
utb.fulltext.faculty Faculty of Technology
utb.fulltext.faculty Faculty of Technology
utb.fulltext.ou Department of Chemistry
utb.fulltext.ou Department of Chemistry
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