N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.ijbiomac.2021.02.031 http://hdl.handle.net/11449/210763 |
Resumo: | 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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N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological propertiesPositively-charged amphiphilic chitosanMucoadhesiveCytocompatibleCancer therapyTwo 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.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Auxilio Financeiro a Projeto Educacional ou de PesquisaSao Paulo State Univ, Inst Chem, Av Prof Francisco Degni 55,237, BR-14800900 Araraquara, SP, BrazilUniv Sao Paulo, Sao Carlos Inst Chem, Av Trabalhador Sao Carlense 400,780, BR-13566590 Sao Carlos, SP, BrazilBrazilian Corp Agr Res, Embrapa Instrumentat, Rua XV Novembro 1452, BR-13560970 Sao Carlos, SP, BrazilSao Paulo State Univ, Sch Pharmaceut Sci, Rod Araraquara Jau Km 01 S-N, BR-14800903 Araraquara, SP, BrazilSao Paulo State Univ, Inst Chem, Av Prof Francisco Degni 55,237, BR-14800900 Araraquara, SP, BrazilSao Paulo State Univ, Sch Pharmaceut Sci, Rod Araraquara Jau Km 01 S-N, BR-14800903 Araraquara, SP, BrazilFAPESP: FAPESP 2016/20970-2FAPESP: 2017/20973-4FAPESP: 2019/13656-8CNPq: CNPq 141353/2016-3CNPq: 150964/2017-0CNPq: 309568/2019-6CAPES: 001Auxilio Financeiro a Projeto Educacional ou de Pesquisa: AUXPE 139/2015Elsevier B.V.Universidade Estadual Paulista (Unesp)Universidade de São Paulo (USP)Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA)Silva, Daniella Souza [UNESP]Facchinatto, William MarcondesSantos, Danilo Martins dosBoni, Fernanda Isadora [UNESP]Valdes, Talita AlvarengaLeitao, AndreiGremiao, Maria Palmira Daflon [UNESP]Colnago, Luiz AlbertoCampana-Filho, Sergio PauloRibeiro, Sidney Jose Lima [UNESP]2021-06-26T06:17:21Z2021-06-26T06:17:21Z2021-05-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article558-568http://dx.doi.org/10.1016/j.ijbiomac.2021.02.031International Journal Of Biological Macromolecules. Amsterdam: Elsevier, v. 178, p. 558-568, 2021.0141-8130http://hdl.handle.net/11449/21076310.1016/j.ijbiomac.2021.02.031WOS:000643948500008Web of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengInternational Journal Of Biological Macromoleculesinfo:eu-repo/semantics/openAccess2024-06-24T13:45:30Zoai:repositorio.unesp.br:11449/210763Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T16:51:42.412791Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties |
title |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties |
spellingShingle |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties Silva, Daniella Souza [UNESP] Positively-charged amphiphilic chitosan Mucoadhesive Cytocompatible Cancer therapy |
title_short |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties |
title_full |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties |
title_fullStr |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties |
title_full_unstemmed |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties |
title_sort |
N-(2-hydroxy)-propyl-3-trimethylammonium, O-palmitoyl chitosan: Synthesis, physicochemical and biological properties |
author |
Silva, Daniella Souza [UNESP] |
author_facet |
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] |
author_role |
author |
author2 |
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] |
author2_role |
author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) Universidade de São Paulo (USP) Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA) |
dc.contributor.author.fl_str_mv |
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] |
dc.subject.por.fl_str_mv |
Positively-charged amphiphilic chitosan Mucoadhesive Cytocompatible Cancer therapy |
topic |
Positively-charged amphiphilic chitosan Mucoadhesive Cytocompatible Cancer therapy |
description |
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. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-06-26T06:17:21Z 2021-06-26T06:17:21Z 2021-05-01 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.ijbiomac.2021.02.031 International Journal Of Biological Macromolecules. Amsterdam: Elsevier, v. 178, p. 558-568, 2021. 0141-8130 http://hdl.handle.net/11449/210763 10.1016/j.ijbiomac.2021.02.031 WOS:000643948500008 |
url |
http://dx.doi.org/10.1016/j.ijbiomac.2021.02.031 http://hdl.handle.net/11449/210763 |
identifier_str_mv |
International Journal Of Biological Macromolecules. Amsterdam: Elsevier, v. 178, p. 558-568, 2021. 0141-8130 10.1016/j.ijbiomac.2021.02.031 WOS:000643948500008 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
International Journal Of Biological Macromolecules |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
558-568 |
dc.publisher.none.fl_str_mv |
Elsevier B.V. |
publisher.none.fl_str_mv |
Elsevier B.V. |
dc.source.none.fl_str_mv |
Web of Science reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808128711166263297 |