Maleimide-Based Thiol Reactive Multiarm Star Polymers via Diels-Alder/Retro Diels-Alder Strategy

被引:34
作者
Gok, Ozgul [1 ]
Durmaz, Hakan [2 ]
Ozdes, Emrah Soner [1 ]
Hizal, Gurkan [2 ]
Tunca, Umit [2 ]
Sanyal, Amitav [1 ]
机构
[1] Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey
[2] Istanbul Tech Univ, Dept Chem, TR-34469 Istanbul, Turkey
关键词
atom transfer polymerization; click conjugation; click reaction; dendrimers; Diels-Alder reaction; functionalizaton of polymers; maleimide polymer; multiarm star polymers; star polymers; LIVING RADICAL POLYMERIZATION; DOUBLE CLICK REACTIONS; BLOCK-COPOLYMERS; MULTIFUNCTIONAL INITIATORS; FUNCTIONALIZED POLYMERS; CHEMISTRY; CORE; DOXORUBICIN; DENDRIMERS; IMMOBILIZATION;
D O I
10.1002/pola.24030
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Multiarm star polymers containing thiol-reactive maleimide groups at their core have been synthesized by utilization of atom transfer radical polymerization (ATRP) of various methacrylates using a masked maleimide containing multiarm initiator One end of the initiator contains multiple halogen groups that produce the star architecture upon polymerization and the other end contains a masked maleimide functional group. Unmasking of the maleimide group after the polymerization provides the thiol reactive maleimide core that is widely used in bioconjugation. Functionalization of the core maleimide group with a thiol containing tripeptide was used to demonstrate facile reactivity of the core of these multiarm polymers under reagent-free conditions (C) 2010 Wiley Periodicals, Inc J Polym Sci Part A. Polym Chem 48 2546-2556, 2010
引用
收藏
页码:2546 / 2556
页数:11
相关论文
共 56 条
[1]   Atom transfer radical polymerization of styrene using a novel octafunctional initiator: Synthesis of well-defined polystyrene stars [J].
Angot, S ;
Murthy, KS ;
Taton, D ;
Gnanou, Y .
MACROMOLECULES, 1998, 31 (21) :7218-7225
[2]   Star-shaped polymers by metal-catalyzed living radical polymerization. 1. Design of Ru(II)-based systems and divinyl linking agents [J].
Baek, KY ;
Kamigaito, M ;
Sawamoto, M .
MACROMOLECULES, 2001, 34 (02) :215-221
[3]   Masked Michael acceptors in poly(phenyleneethynylene)s for facile conjugation [J].
Bailey, GC ;
Swager, TM .
MACROMOLECULES, 2006, 39 (08) :2815-2818
[4]   Synthesis of Semitelechelic Maleimide Poly(PEGA) for Protein Conjugation By RAFT Polymerization [J].
Bays, Emmanuelle ;
Tao, Lei ;
Chang, Chien-Wen ;
Maynard, Heather D. .
BIOMACROMOLECULES, 2009, 10 (07) :1777-1781
[5]   Bioapplications of RAFT Polymerization [J].
Boyer, Cyrille ;
Bulmus, Volga ;
Davis, Thomas P. ;
Ladmiral, Vincent ;
Liu, Jingquan ;
Perrier, Sebastien .
CHEMICAL REVIEWS, 2009, 109 (11) :5402-5436
[6]   Polymeric Phosphorylcholine-Camptothecin Conjugates Prepared by Controlled Free Radical Polymerization and Click Chemistry [J].
Chen, Xiangji ;
McRae, Samantha ;
Parelkar, Sangram ;
Emrick, Todd .
BIOCONJUGATE CHEMISTRY, 2009, 20 (12) :2331-2341
[7]   Synthesis of multiarm star poly(glycerol)-block-poly(2-hydroxyethyl methacrylate) [J].
Chen, Y ;
Shen, Z ;
Barriau, E ;
Kautz, H ;
Frey, H .
BIOMACROMOLECULES, 2006, 7 (03) :919-926
[8]   Heterograft Copolymers via Double Click Reactions Using One-Pot Technique [J].
Dag, Aydan ;
Durmaz, Hakan ;
Demir, Emrah ;
Hizal, Gurkan ;
Tunca, Umit .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (20) :6969-6977
[9]   Preparation of 3-arm star polymers (A3) via Diels-Alder click reaction [J].
Dag, Aydan ;
Durmaz, Hakan ;
Hizal, Gurkan ;
Tunca, Umit .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (01) :302-313
[10]   Multiarm Star Block Copolymers via Diels-Alder Click Reaction [J].
Dag, Aydan ;
Durmaz, Hakan ;
Tunca, Umit ;
Hizal, Gurkan .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (01) :178-187