Synthesis of a New Poly(ε‐caprolactone)‐g‐Chitosan Amphiphilic Graft Copolymer with a “Reverse” Structure

Author:

Delorme Victor1,David Ghislain2,Dejean Stéphane1,Mouton Julia34,Garric Xavier15,Coudane Jean1ORCID,Van Den Berghe Hélène1

Affiliation:

1. IBMM (Institut des Biomolécules Max Mousseron) CNRS Department Polymers for Health and Biomaterials Montpellier University ENSCM Pôle Chimie Balard 1919 route de Mende cedex 5 Montpellier 34090 France

2. ICG (Institut Charles Gerhardt) CNRS Montpellier University ENSCM Pôle Chimie Balard 1919 route de Mende cedex 5 Montpellier 34090 France

3. Polymers composites and hybrids (PCH) IMT Mines d'Alès Alès 30100 France

4. EPF Graduate School of Engineering Montpellier 34000 France

5. Department of Pharmacy Nîmes University Hospital Nimes 30900 France

Abstract

AbstractHydrophilic chitosan (CHT) and hydrophobic polyε‐caprolactone (PCL) are well‐known biocompatible and biodegradable polymers that have many applications in the biomedical and pharmaceutical fields. But the mixtures of these two compounds are considered incompatible, which makes them not very interesting. To avoid this problem and to further extend the properties of these homopolymers, the synthesis of a new graft copolymer, the fully biodegradable amphiphilic poly(ε‐caprolactone‐g‐chitosan) (PCL‐g‐CHT) is described, with an unusual “reverse” structure formed by a PCL backbone with CHT grafts, unlike the “classic” CHT‐g‐PCL structure with a CHT main chain and PCL grafts. This copolymer is prepared via a copper‐catalyzed 1,3‐dipolar Huisgen cycloaddition between propargylated PCL (PCL‐yne) and a new azido‐chitosan (CHT‐N3). In order to obtain an amphiphilic copolymer regardless of the pH, chitosan oligomers, soluble at any pH, are prepared and used. The amphiphilic PCL‐g‐CHT copolymer spontaneously self‐assembles in water into nanomicelles that may incorporate hydrophobic drugs to give novel drug delivery systems.

Funder

Ministère de l'Enseignement Supérieur et de la Recherche

Publisher

Wiley

Subject

Materials Chemistry,Polymers and Plastics,Organic Chemistry

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