Synthesis of a novel structural triblock copolymer of poly(γ-benzyl-L-glutamic acid)-b-poly(ethylene oxide)-b-poly(ε-caprolactone)

被引:53
作者
Deng, MX [1 ]
Wang, R [1 ]
Rong, GZ [1 ]
Sun, JR [1 ]
Zhang, XF [1 ]
Chen, XS [1 ]
Jing, XB [1 ]
机构
[1] Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Jilin, Peoples R China
基金
中国国家自然科学基金;
关键词
biodegradation; poly(epsilon-caprolactone); poly(ethylene oxide); poly(gamma-benzyl-L-glutamic acid); triblock copolymer;
D O I
10.1016/j.biomaterials.2003.10.018
中图分类号
R318 [生物医学工程];
学科分类号
0831 ;
摘要
A novel structural triblock copolymer of poly(gamma-benzyl-L-glutamic acid)-b-poly(ethylene oxide)-b-poly(epsilon-caprolactone) (PBLG-PEO-PCL) was synthesized by a new approach in the following three steps: (1) sequential anionic ring opening polymerization (ROP) of ethylene oxide and epsilon-caprolactone with an acetonitrile/potassium naphthalene initiator system to obtain a diblock copolymer CN-PEO-PCL with a cyano end-group; (2) conversion of the CN end-group into NH2 end-group by hydrogenation to obtain NH2-PEO-PCL; (3) ROP of gamma-benzyl-L-glutamate-N-carboxyanhydrides (Bz-L-GluNCA) with NH2-PEO-PCL as macroinitiator to obtain the target triblock copolymer. The structures from CN-PEO precursor to the triblock copolymers were confirmed by FT-IR and H-1 NMR spectroscopy, and their molecular weights were measured by gel permeation chromatography. The monomer of Bz-L-GluNCA can react almost quantitatively with the amino end-groups of NH2-PEO-PCL macroinitiator by ROP. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3553 / 3558
页数:6
相关论文
共 22 条
[1]   LACTONE POLYMERIZATION AND POLYMER PROPERTIES [J].
BRODE, GL ;
KOLESKE, JV .
JOURNAL OF MACROMOLECULAR SCIENCE-CHEMISTRY, 1972, A 6 (06) :1109-1144
[2]   HETEROBIFUNCTIONAL POLY(ETHYLENE OXIDE) - SYNTHESIS OF ALPHA-METHOXY-OMEGA-AMINO AND ALPHA-HYDROXY-OMEGA-AMINO PEOS WITH THE SAME MOLECULAR-WEIGHTS [J].
CAMMAS, S ;
NAGASAKI, Y ;
KATAOKA, K .
BIOCONJUGATE CHEMISTRY, 1995, 6 (02) :226-230
[3]   Synthesis of a barbell-like triblock copolymer, poly(L-lysine) dendrimer-block-poly(ethylene glycol)-block-poly(L-lysine) dendrimer, and its self-assembly with plasmid DNA [J].
Choi, JS ;
Joo, DK ;
Kim, CH ;
Kim, K ;
Park, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (03) :474-480
[4]  
CHRISTINE A, 2000, J CONTROL RELEASE, V63, P275
[5]   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
[6]   MACROMOLECULAR ENGINEERING OF POLYLACTONES AND POLYLACTIDES .9. SYNTHESIS, CHARACTERIZATION, AND APPLICATION OF OMEGA-PRIMARY AMINE POLY(EPSILON-CAPROLACTONE) [J].
DEGEE, P ;
DUBOIS, P ;
JEROME, R ;
TEYSSIE, P .
MACROMOLECULES, 1992, 25 (17) :4242-4248
[7]   BIOLOGICAL RESPONSES TO POLYETHYLENE OXIDE MODIFIED POLYETHYLENE TEREPHTHALATE SURFACES [J].
DESAI, NP ;
HUBBELL, JA .
JOURNAL OF BIOMEDICAL MATERIALS RESEARCH, 1991, 25 (07) :829-843
[8]   SIMPLE PREPARATION OF A VERY ACTIVE RANEY NICKEL CATALYST [J].
DOMINGUEZ, X ;
LOPEZ, IC ;
FRANCO, R .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) :1625-&
[9]   THE CLINICAL EFFICACY OF POLY(ETHYLENE GLYCOL)-MODIFIED PROTEINS [J].
FUERTGES, F ;
ABUCHOWSKI, A .
JOURNAL OF CONTROLLED RELEASE, 1990, 11 (1-3) :139-148
[10]   OXIDATION OF POLYETHYLENE GLYCOLS BY ALCOHOL-DEHYDROGENASE [J].
HEROLD, DA ;
KEIL, K ;
BRUNS, DE .
BIOCHEMICAL PHARMACOLOGY, 1989, 38 (01) :73-76