N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties

Two samples of N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan (DPCat) with different av-erage degrees of quaternization named as DPCat35 (DQ = 35%) and DPCat80 (DQ = 80%), were successfully syn-thesized by reacting glycidyltrimethylammonium chloride (GTMAC) with O-palmitoyl chitosan...

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Detalles Bibliográficos
Autores: Silva, Daniella Souza [UNESP], Facchinatto, William Marcondes, Santos, Danilo Martins dos, Boni, Fernanda Isadora [UNESP], Valdes, Talita Alvarenga, Leitao, Andrei, Gremiao, Maria Palmira Daflon [UNESP], Colnago, Luiz Alberto, Campana-Filho, Sergio Paulo, Ribeiro, Sidney Jose Lima [UNESP]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:Brasil
Institución:Universidade Estadual Paulista (UNESP)
Repositorio:Repositório Institucional da UNESP
Idioma:inglés
OAI Identifier:oai:repositorio.unesp.br:11449/210763
Acceso en línea:http://dx.doi.org/10.1016/j.ijbiomac.2021.02.031
http://hdl.handle.net/11449/210763
Access Level:acceso abierto
Palabra clave:Positively-charged amphiphilic chitosan
Mucoadhesive
Cytocompatible
Cancer therapy
Descripción
Sumario:Two samples of N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan (DPCat) with different av-erage degrees of quaternization named as DPCat35 (DQ = 35%) and DPCat80 (DQ = 80%), were successfully syn-thesized by reacting glycidyltrimethylammonium chloride (GTMAC) with O-palmitoyl chitosan (DPCh) derivative (DS = 12%). Such amphiphilic derivatives of chitosan were fully water-soluble at 1.0 < pH < 12.0 and showed significant electrostatic stability enhancement of a self-assembly micellar nanostructure (100 & ndash;320 nm) due to its positively-charged out-layer. In vitro mucoadhesive and cytotoxicity essays toward healthy fibroblast cells (Balb/C 3T3 clone A31 cell), human prostate cancer (DU145) and liver cancer (HepG2/ C3A) cell lines revealed that the biological properties of DPCat derivatives were strongly dependent on DQ. Ad-ditionally, DPCat35 had better interactions with the biological tissue and with mucin glycoproteins at pH 7.4 as well as exhibited potential to be used on the development of drug delivery systems for prostate and liver cancer treatment. (c) 2021 Elsevier B.V. All rights reserved.

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