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Synthesis and micellization of an amphiphilic biodegradable β-cyclodextrin/poly(γ-benzyl L-glutamate) copolymer

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Abstract

β-Cyclodextrin/poly(γ-benzyl L-glutamate) (β-CD-PBLG) copolymers were synthesized by ring-opening polymerization of N-carboxy-γ-benzyl L-glutamate anhydride (BLG-NCA) in N,N-dimethylformamide(DMF) initiated by mono-6-amino-β-cyclodextrin(H2N-β-CD). The structures of the copolymers were determined by IR, 1H NMR and GPC. The fluorescence technique was used to determine the critical micelle concentration (CMC) of copolymer micelle solution. The diameter and the distribution of micelles were characterized by dynamic light scattering(DLS) and its shape was observed by transmission electron microscopy(TEM). The results showed that BLG-NCA could be initiated by H2N-β-CD to produce copolymer. These copolymers showed an amphiphilic nature and could self-assemble into nano-micelles in water. The CMC of copolymer solution and the size of micelle reduced with the increasing of the proportion of hydrophobic parts. TEM images demonstrated the micelles are all spherical. Such copolymers could be expected to find applications in drug delivery systems and other biomedical domains.

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Abbreviations

β-CD-PBLG :

β-Cyclodextrin/poly(γ-benzyl L-glutamate)

BLG-NCA :

N-carboxy-γ-benzyl L-glutamate anhydride

DMF :

N,N-dimethylformamide

H 2 N-β-CD :

mono-6-amino-β-cyclodextrin

CMC :

critical micelle concentrations

DLS :

dynamic light scattering

TEM :

transmission electron microscopy

PAA :

poly(α-amino acid)s

PEG :

poly(ethylene glycol)

TsCl :

p-toluenesulfonyl chloride

THF :

tetrahydrofuran

TsO-β-CD :

mono-6-(p-tolylsulfonyl)-β-cyclodextrin

N 3 -β-CD :

mono-6-azido-β-cyclodextrin

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Acknowledgements

The authors are indebted to the Natural Science Foundation for Education Department of Liaoning Province of China (No. 2007T051).

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Authors and Affiliations

  1. Key Laboratory of Green Synthesis and Preparative Chemistry of Advanced Materials, The Education Department of Liaoning Province, College of Chemistry, Liaoning University, Shenyang, 110036, People’s Republic of China

    Qiu Hua Wu, Fang Liang, Tian Zhu Wei, Xi Ming Song, Da Liang Liu & Guo Lin Zhang

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  1. Qiu Hua Wu
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  2. Fang Liang
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  3. Tian Zhu Wei
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Correspondence to Guo Lin Zhang.

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The Natural Science Foundation for Education Department of Liaoning Province of China (No. 2007T051).

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Wu, Q.H., Liang, F., Wei, T.Z. et al. Synthesis and micellization of an amphiphilic biodegradable β-cyclodextrin/poly(γ-benzyl L-glutamate) copolymer. J Polym Res 17, 183–190 (2010). https://doi.org/10.1007/s10965-009-9304-9

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