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An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives

Chitosan, a chitin-derivative polysaccharide, known for its non-toxicity, biocompatibility and biodegradability, presents limited applications due to its low solubility in neutral or basic pH medium. Quaternization stands out as an alternative to modify this natural polymer, aiming to improve its so...

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Autores principales: Freitas, Emanuelle Dantas, Moura Jr., Celso Fidelis, Kerwald, Jonas, Beppu, Marisa Masumi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7759937/
https://www.ncbi.nlm.nih.gov/pubmed/33266285
http://dx.doi.org/10.3390/polym12122878
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author Freitas, Emanuelle Dantas
Moura Jr., Celso Fidelis
Kerwald, Jonas
Beppu, Marisa Masumi
author_facet Freitas, Emanuelle Dantas
Moura Jr., Celso Fidelis
Kerwald, Jonas
Beppu, Marisa Masumi
author_sort Freitas, Emanuelle Dantas
collection PubMed
description Chitosan, a chitin-derivative polysaccharide, known for its non-toxicity, biocompatibility and biodegradability, presents limited applications due to its low solubility in neutral or basic pH medium. Quaternization stands out as an alternative to modify this natural polymer, aiming to improve its solubility over a wide pH range and, consequently, expand its range of applications. Quaternization occurs by introducing a quaternary ammonium moiety onto or outside the chitosan backbone, via chemical reactions with primary amino and hydroxyl groups, under vast experimental conditions. The oldest and most common forms of quaternized chitosan involve N,N,N-trimethyl chitosan (TMC) and N-[(2-hydroxy-3-trimethyl ammonium) propyl] chitosan (HTCC) and, more recently, quaternized chitosan by insertion of pyridinium or phosphonium salts. By modifying chitosan through the insertion of a quaternary moiety, permanent cationic charges on the polysaccharide backbone are achieved and properties such as water solubility, antimicrobial activity, mucoadhesiveness and permeability are significantly improved, enabling the application mainly in the biomedical and pharmaceutical areas. In this review, the main quaternized chitosan compounds are addressed in terms of their structure, properties, synthesis routes and applications. In addition, other less explored compounds are also presented, involving the main findings and future prospects regarding the field of quaternized chitosans.
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spelling pubmed-77599372020-12-26 An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives Freitas, Emanuelle Dantas Moura Jr., Celso Fidelis Kerwald, Jonas Beppu, Marisa Masumi Polymers (Basel) Review Chitosan, a chitin-derivative polysaccharide, known for its non-toxicity, biocompatibility and biodegradability, presents limited applications due to its low solubility in neutral or basic pH medium. Quaternization stands out as an alternative to modify this natural polymer, aiming to improve its solubility over a wide pH range and, consequently, expand its range of applications. Quaternization occurs by introducing a quaternary ammonium moiety onto or outside the chitosan backbone, via chemical reactions with primary amino and hydroxyl groups, under vast experimental conditions. The oldest and most common forms of quaternized chitosan involve N,N,N-trimethyl chitosan (TMC) and N-[(2-hydroxy-3-trimethyl ammonium) propyl] chitosan (HTCC) and, more recently, quaternized chitosan by insertion of pyridinium or phosphonium salts. By modifying chitosan through the insertion of a quaternary moiety, permanent cationic charges on the polysaccharide backbone are achieved and properties such as water solubility, antimicrobial activity, mucoadhesiveness and permeability are significantly improved, enabling the application mainly in the biomedical and pharmaceutical areas. In this review, the main quaternized chitosan compounds are addressed in terms of their structure, properties, synthesis routes and applications. In addition, other less explored compounds are also presented, involving the main findings and future prospects regarding the field of quaternized chitosans. MDPI 2020-11-30 /pmc/articles/PMC7759937/ /pubmed/33266285 http://dx.doi.org/10.3390/polym12122878 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Freitas, Emanuelle Dantas
Moura Jr., Celso Fidelis
Kerwald, Jonas
Beppu, Marisa Masumi
An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives
title An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives
title_full An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives
title_fullStr An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives
title_full_unstemmed An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives
title_short An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives
title_sort overview of current knowledge on the properties, synthesis and applications of quaternary chitosan derivatives
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7759937/
https://www.ncbi.nlm.nih.gov/pubmed/33266285
http://dx.doi.org/10.3390/polym12122878
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