Synthesis, characterization and self-assemble behavior of chitosan-O-poly(ε-caprolactone)

Biodegradable tri-component graft copolymers, chitosan-poly(ε-caprolactone)-poly(ethylene glycol) (CPP), were synthesized via a mild route, using sodium dodecyl sulfate-chitosan complex (SCC) as a precursor. Both PCL and PEG could be conveniently conjugated to the hydroxyl sites of chitosan without the need of tedious chemical protection/deprotection processes, thereby leaving the amino groups of chitosan intact. The self-assembly and release behavior of the copolymer micelles were investigated. Paclitaxel and rutin were used as model drugs. Spherical micelles could be formed through self-assembly of CPP in aqueous media. The micelle diameter increased with PEGylation degree and ranged from 30 to 45 nm. The incorporation of drugs into the micelles significantly raised the micelle diameter and diversified the micelle morphologies. The micelles were further subjected to glutaraldehyde treatment to prolong the release of the incorporated drugs. It was found that the crosslinking process shrunk the drug-loaded micelles. In addition, the micelles were endowed with self-luminescent properties after crosslinked with glutaraldehyde. By increasing crosslinking density, the release duration of the model drugs could be prolonged.

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“…SCC‐ O ‐PCL and PEG‐NCO were synthesized according to the procedures previously reported 27. 0.5 g of SCC‐ O ‐PCL was dissolved in 15 mL of DMSO.…”

Section: Methodsmentioning

confidence: 99%

Chitosan‐poly(ε‐caprolactone)‐poly(ethylene glycol) graft copolymers: Synthesis, self‐assembly, and drug release behavior

Chen

Cai

Zhang

et al. 2010

J Biomedical Materials Res

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“…It is known that chitosan, with a repeating unit of glucosamine, which possesses unique polycationic nature in acidic condition, can form complex with anions. For example, Cai, Jiang, Chen, et al (2009); prepared sodium dodecyl sulfate-chitosan complex (SCC), which substantially enhances the solubility of chitosan in organic solvents. And it should be noted that SCC is a good intermediate for regioselectively grafting polymers onto chitosan through hydroxyl groups.…”

Section: Synthesis and Nmr Analysismentioning

confidence: 99%

Modification of chitosan with monomethyl fumaric acid in an ionic liquid solution

Wang

Zheng

et al. 2015

Carbohydrate Polymers

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“…In order to synthesize macromolecular RAFT agent, chitosan was first reacted with 4-methylbenzenesulfonic acid according to the modified literature method [31], and then with DDACT to serve as RAFT agent (Scheme S1). The structures of MBSA-chitosan complex and MBSA-Chitosan-RAFT agent were confirmed by 1 H NMR spectra (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…MBSA-chitosan complex was prepared according to the modified literature method [31]. After chitosan (0.322 g, 2 mmol repeating unit) and MBSA (0.412 g, 2.4 mmol) were completely dissolved in 20 mL of distilled water at room temperature, the mixture was poured into 10-fold acetone.…”

Section: Preparation Of Mbsa-chitosan Complexmentioning

confidence: 99%

Synthesis and property of chitosan graft copolymer by RAFT polymerization with tosylic acid–chitosan complex

Jiang

Pan

Cao

et al. 2012

International Journal of Biological Macromolecules

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Synthesis, characterization and self-assemble behavior of chitosan-O-poly(ε-caprolactone)

Cited by 39 publications

References 30 publications

Chitosan‐poly(ε‐caprolactone)‐poly(ethylene glycol) graft copolymers: Synthesis, self‐assembly, and drug release behavior

Chitosan‐poly(ε‐caprolactone)‐poly(ethylene glycol) graft copolymers: Synthesis, self‐assembly, and drug release behavior

Modification of chitosan with monomethyl fumaric acid in an ionic liquid solution

Synthesis and property of chitosan graft copolymer by RAFT polymerization with tosylic acid–chitosan complex

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