New amphiphilic biodegradable β-cyclodextrin/poly(L-leucine) copolymers: Synthesis, characterization, and micellization

被引:17
作者
Zhang, Guolin [1 ]
Liang, Fang [1 ]
Song, Ximing [1 ]
Liu, Daliang [1 ]
Li, Mengjiang [1 ]
Wu, Qiuhua [1 ]
机构
[1] Liaoning Univ, Key Lab Green Synth & Preparat Chem Adv Mat, Educ Dept Liaoning Prov, Coll Chem, Shenyang 110036, Peoples R China
关键词
beta-Cyclodextrin; Poly(L-leucine); Amphiphilic biodegradable copolymers; Micelles; POLYION COMPLEX MICELLES; BLOCK-COPOLYMER; DRUG-DELIVERY; N-CARBOXYANHYDRIDES; BETA-CYCLODEXTRIN; POLY(AMINO ACID)S; POLY(ETHYLENE; POLYMERIZATION; OXIDE);
D O I
10.1016/j.carbpol.2010.01.003
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new amphiphilic biodegradable beta-cyclodextrin/poly(L-leucine) (beta-CD-PLLA) copolymer was synthesized by ring-opening polymerization of N-carboxy-L-alanine anhydride (LL-NCA) in N,N-dimethylformamide (DMF) initiated by mono-6-amino-beta-cyclodextrin (H2N-beta-CD). The structures of the copolymers were determined by IR, H-1 NMR and GPC. The fluorescence technique was used to determine the critical micelle concentrations (CMC) of copolymer micelle solution. The diameter and distribution of micelles were characterized by dynamic light scattering (DLS) and its shape was observed by transmission electron microscopy (TEM). The results showed that LL-NCA could be initiated by H2N-beta-CD to produce the copolymer. These copolymers could self-assemble into nano-micelles in water. The CMC of copolymer solution and the size of micelle reduced with increasing proportion of the hydrophobic part. TEM images demonstrated the micelles are all spherical. Such block copolymers could be expected to find applications in drug delivery systems and other biomedical fields. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:885 / 890
页数:6
相关论文
共 24 条
[1]   Biodegradable poly(ethylene glycol)-co-poly(L-lysine)-g-histidine multiblock copolymers for nonviral gene delivery [J].
Bikram, M ;
Ahn, CH ;
Chae, SY ;
Lee, MY ;
Yockman, JW ;
Kim, SW .
MACROMOLECULES, 2004, 37 (05) :1903-1916
[2]   THE PREPARATION OF N-CARBOXYANHYDRIDES OF ALPHA-AMINO-ACIDS USING BIS(TRICHLOROMETHYL)CARBONATE [J].
DALY, WH ;
POCHE, D .
TETRAHEDRON LETTERS, 1988, 29 (46) :5859-5862
[3]   A biodegradable triblock copolymer poly(ethylene glycol)-b-poly(L-lactide)-b-poly(L-lysine): Synthesis, self-assembly and RGD peptide modification [J].
Deng, Chao ;
Chen, Xuesi ;
Yu, Haijun ;
Sun, Jing ;
Lu, Tiancheng ;
Jing, Xiabin .
POLYMER, 2007, 48 (01) :139-149
[4]   Polymerization of polyfunctional macromolecules: Synthesis of a new class of high molecular weight poly(amino acid)s by oxidative coupling of phenol-containing precursor polymers [J].
Fukuoka, T ;
Uyama, H ;
Kobayashi, S .
BIOMACROMOLECULES, 2004, 5 (03) :977-983
[5]   Synthesis of a biodegradable tadpole-shaped polymer via the coupling reaction of polylactide onto mono(6-(2-aminoethyl)amino-6-deoxy)-β-cyclodextrin and its properties as the new carrier of protein delivery system [J].
Gao, H ;
Wang, YN ;
Fan, YG ;
Ma, JB .
JOURNAL OF CONTROLLED RELEASE, 2005, 107 (01) :158-173
[6]   Polymerisation of β-cyclodextrin with succinic anhydride.: Synthesis, characterisation, and ion flotation of transition metals [J].
Girek, T ;
Kozlowski, CA ;
Koziol, JJ ;
Walkowiak, W ;
Korus, I .
CARBOHYDRATE POLYMERS, 2005, 59 (02) :211-215
[7]   AMINO-TERMINED POLY(L-LACTIDE)S AS INITIATORS FOR THE POLYMERIZATION OF N-CARBOXYANHYDRIDES - SYNTHESIS OF POLY(L-LACTIDE)-BLOCK-POLY(ALPHA-AMINO ACID)S [J].
GOTSCHE, M ;
KEUL, H ;
HOCKER, H .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 1995, 196 (12) :3891-3903
[9]   FORMATION OF POLYION COMPLEX MICELLES IN AN AQUEOUS MILIEU FROM A PAIR OF OPPOSITELY-CHARGED BLOCK-COPOLYMERS WITH POLY(ETHYLENE GLYCOL) SEGMENTS [J].
HARADA, A ;
KATAOKA, K .
MACROMOLECULES, 1995, 28 (15) :5294-5299
[10]   A novel surgical glue composed of gelatin and N-hydroxysuccinimide activated poly(L-glutamic acid):: Part 1.: Synthesis of activated poly(L-glutamic acid) and its gelation with gelatin [J].
Iwata, H ;
Matsuda, S ;
Mitsuhashi, K ;
Itoh, E ;
Ikada, Y .
BIOMATERIALS, 1998, 19 (20) :1869-1876