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

被引:7
作者
Wu, Qiu Hua [1 ]
Liang, Fang [1 ]
Wei, Tian Zhu [1 ]
Song, Xi Ming [1 ]
Liu, Da Liang [1 ]
Zhang, Guo Lin [1 ]
机构
[1] Liaoning Univ, Coll Chem, Educ Dept Liaoning Prov, Key Lab Green Synth & Preparat Chem Adv Mat, Shenyang 110036, Peoples R China
关键词
beta-Cyclodextrin; Poly(gamma-benzyl-L-glutamate); Amphiphilic biodegradable copolymers; Micelles; POLYION COMPLEX MICELLES; BLOCK-COPOLYMER; DRUG-DELIVERY; BETA-CYCLODEXTRIN; POLY(AMINO ACID)S; POLY(ETHYLENE; POLYMERIZATION; DERIVATIVES; OXIDE);
D O I
10.1007/s10965-009-9304-9
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
beta-Cyclodextrin/poly(gamma-benzyl L-glutamate) (beta-CD-PBLG) copolymers were synthesized by ring-opening polymerization of N-carboxy-gamma-benzyl L-glutamate anhydride (BLG-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 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-beta-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.
引用
收藏
页码:183 / 190
页数:8
相关论文
共 27 条
[1]   Fluorescent indolizine-β-cyclodextrin derivatives for the detection of Volatile Organic Compounds [J].
Becuwe, Matthieu ;
Landy, David ;
Delattre, Francois ;
Cazier, Francine ;
Fourmentin, Sophie .
SENSORS, 2008, 8 (06) :3689-3705
[2]   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
[3]   POLYPEPTIDES .3. THE SYNTHESIS OF HIGH MOLECULAR WEIGHT POLY-GAMMA-BENZYL-L-GLUTAMATES [J].
BLOUT, ER ;
KARLSON, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (05) :941-946
[4]   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
[5]   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
[6]   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
[7]   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
[8]  
Goshen M., 1995, MACROMOL CHEM PHYS, V196, P3891
[10]   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