Novel amphiphilic diblock copolymers bearing acid-labile oxazolidine moieties: Synthesis, self-assembly and responsive behavior in aqueous solution

被引:20
作者
Cui, Qianling [1 ,2 ]
Wu, Feipeng [1 ]
Wang, Erjian [1 ]
机构
[1] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China
关键词
Amphiphilic diblock copolymers; pH-responsivity; RAFT polymerization; TRANSFER RADICAL POLYMERIZATION; WATER-SOLUBLE POLYMERS; DRUG-DELIVERY SYSTEMS; CROSS-LINKED MICELLES; BLOCK-COPOLYMERS; POLY(ORTHO ESTERS); HYDROLYSIS; RELEASE; GLYCOL); MICELLIZATION;
D O I
10.1016/j.polymer.2011.02.022
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A novel oxazolidine based acid-labile monomer N-acryloyl-2,2-dimethyl-1,3-oxazolidine (ADMO) was synthesized and polymerized by reversible addition fragmentation chain transfer (RAFT) polymerization using poly(ethylene glycol) based chain transfer agent (PEG-CTA). The diblock copolymers PEG-b-PADMO were composed of hydrophilic PEG with fixed length and hydrophobic PADMO with different lengths, which formed core-shell micelles in water. Morphologies and sizes of micelles were obtained by transmission electron microscopy (TEM) and dynamic light scattering (DLS), which showed that the shapes of polymeric aggregates developed from small spherical micelles, worm-like micelles to larger size of vesicles, as the length of PADMO increased. The hydrolysis kinetics of the micelles was studied using H-1 NMR, DLS and release of loaded Nile Red dye, whose rate strongly depended on pH and micellar structure. It led to the disruption of polymeric micelles and concomitant release of the guest molecules, due to the transformation of hydrophobic PADMO into hydrophilic poly(2-hydroxyethyl acrylamide) (PHEAM). (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1755 / 1765
页数:11
相关论文
共 76 条
[51]   Stereoelectronic control of oxazolidine ring-opening:: structural and chemical evidences [J].
Sélambarom, J ;
Monge, S ;
Carré, F ;
Roque, JP ;
Pavia, AA .
TETRAHEDRON, 2002, 58 (47) :9559-9566
[52]   Block length dependence of morphological phase diagrams of the ternary system of PS-b-PAA/dioxane/H2O [J].
Shen, HW ;
Eisenberg, A .
MACROMOLECULES, 2000, 33 (07) :2561-2572
[53]   Acid-labile polyvinylamine micro- and nanogel capsules [J].
Shi, Lianjun ;
Berkland, Cory .
MACROMOLECULES, 2007, 40 (13) :4635-4643
[54]   Tuning Nanostructure Morphology and Gold Nanoparticle "Locking" of Multi-Responsive Amphiphilic Diblock Copolymers [J].
Smith, Adam E. ;
Xu, Xuewei ;
Abell, Thomas U. ;
Kirkland, Stacey E. ;
Hensarling, Ryan M. ;
McCormick, Charles L. .
MACROMOLECULES, 2009, 42 (08) :2958-2964
[55]   Physicochemical characterization of degradable thermosensitive polymeric micelles [J].
Soga, O ;
van Nostrum, CF ;
Ramzi, A ;
Visser, T ;
Soulimani, F ;
Frederik, PM ;
Bomans, PHH ;
Hennink, WE .
LANGMUIR, 2004, 20 (21) :9388-9395
[56]   RAFT polymerization: an avenue to functional polymeric micelles for drug delivery [J].
Stenzel, Martina Heide .
CHEMICAL COMMUNICATIONS, 2008, (30) :3486-3503
[57]   Superparamagnetic Iron Oxide Nanoparticles Encapsulated in Biodegradable Thermosensitive Polymeric Micelles: Toward a Targeted Nanomedicine Suitable for Image-Guided Drug Delivery [J].
Talelli, Marina ;
Rijcken, Cristianne J. F. ;
Lammers, Twan ;
Seevinck, Peter R. ;
Storm, Gert ;
van Nostrum, Cornelus F. ;
Hennink, Wim E. .
LANGMUIR, 2009, 25 (04) :2060-2067
[58]   Amphiphilic Block Copolymers Bearing Ortho Ester Side-Chains: pH-Dependent Hydrolysis and Self-Assembly in Water [J].
Tang, Rupei ;
Ji, Weihang ;
Wang, Chun .
MACROMOLECULAR BIOSCIENCE, 2010, 10 (02) :192-201
[59]   Poly(ortho ester amides): Acid-Labile Temperature-Responsive Copolymers for Potential Biomedical Applications [J].
Tang, Rupei ;
Palumbo, R. Noelle ;
Ji, Weihang ;
Wang, Chun .
BIOMACROMOLECULES, 2009, 10 (04) :722-727
[60]   AN INVESTIGATION OF THE ROTATIONAL ISOMERS OF N-ACETYL-2,2-DIMETHYLOXAZOLIDINE AND RELATED-COMPOUNDS BY NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPY AND MOLECULAR MECHANICS [J].
TAYLOR, WG ;
HALL, TW ;
SCHRECK, CE .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (01) :165-172