Click reactions in chitosan chemistry

被引:47
作者
Kritchenkov, A. S. [1 ,2 ]
Skorik, Yu. A. [1 ,3 ]
机构
[1] Russian Acad Sci, Inst Macromol Cpds, 31 Bolshoi Prosp Vasilevskogo Ostrova, St Petersburg 199004, Russia
[2] RUDN Univ, 6 Ul Miklukho-Maklaya, Moscow 117198, Russia
[3] Fed Almazov North West Med Res Ctr, 2 Ul Akkuratova, St Petersburg 197341, Russia
基金
俄罗斯基础研究基金会;
关键词
chitosan; click reactions; azide-alkyne cycloaddition; thiol-ene addition; chitosan derivatives; pre-click modification; CONTROLLED DRUG-RELEASE; FUNCTIONALIZED CHITOSAN; HYDROGELS; DERIVATIVES; CHITIN; CYCLOADDITION; BIOMATERIALS; NANOPARTICLES; COPOLYMERS; CATALYSIS;
D O I
10.1007/s11172-017-1809-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The review provides the first generalized and systematized information on the use of click reactions in chitosan chemistry for the preparation of novel polymers with attractive physicochemical and biological properties. The reactions of copper-catalyzed azide-alkyne cycloaddition and the click reactions of chitosan derivatives occurring in the absence of salts or metal complexes are discussed in detail. The data on the pre-click modification of chito-san (i.e., the introduction of azide function, alkyne fragment, highly dipolarophilic moieties, and thiol group into the polymer) are reviewed. Special attention is given to the application of new chitosan derivatives obtained by click modification.
引用
收藏
页码:769 / 781
页数:13
相关论文
共 74 条
[21]   Preparation of highly regioselective chitosan derivatives via "click chemistry" [J].
Ifuku, Shinsuke ;
Wada, Masahiro ;
Morimoto, Minoru ;
Saimoto, Hiroyuki .
CARBOHYDRATE POLYMERS, 2011, 85 (03) :653-657
[22]   Biomaterials based on chitin and chitosan in wound dressing applications [J].
Jayakumar, R. ;
Prabaharan, M. ;
Kumar, P. T. Sudheesh ;
Nair, S. V. ;
Tamura, H. .
BIOTECHNOLOGY ADVANCES, 2011, 29 (03) :322-337
[23]   Rapid Cu-Free Click Chemistry with Readily Synthesized Biarylazacyclooctynones [J].
Jewett, John C. ;
Sletten, Ellen M. ;
Bertozzi, Carolyn R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3688-+
[24]   Rapid Hybridization of Chitosan-Gold-Antibodies via Metal-free Click in Water-based Systems: A Model Approach for Naked-eye Detectable Antigen Sensors [J].
Jirawutthiwongchai, Jatesuda ;
Draeger, Gerald ;
Chirachanchai, Suwabun .
MACROMOLECULAR RAPID COMMUNICATIONS, 2014, 35 (13) :1204-1210
[25]   Chitosan-Oxanorbornadiene: A Convenient Chitosan Derivative for Click Chemistry without Metal Catalyst Problem [J].
Jirawutthiwongchai, Jatesuda ;
Krause, Andreas ;
Draeger, Gerald ;
Chirachanchai, Suwabun .
ACS MACRO LETTERS, 2013, 2 (03) :177-180
[26]   Fabrication of Chitosan-Poly(ethylene glycol) Hybrid Hydrogel Microparticles via Replica Molding and Its Application toward Facile Conjugation of Biomolecules [J].
Jung, Sukwon ;
Yi, Hyunmin .
LANGMUIR, 2012, 28 (49) :17061-17070
[27]   Fluorescently Labeled Risedronate and Related Analogues: "Magic Linker" Synthesis [J].
Kashemirov, Boris A. ;
Bala, Joy Lynn F. ;
Chen, Xiaolan ;
Ebetino, F. H. ;
Xia, Zhidao ;
Russell, R. Graham G. ;
Coxon, Fraser P. ;
Roelofs, Anke J. ;
Rogers, Michael J. ;
McKenna, Charles E. .
BIOCONJUGATE CHEMISTRY, 2008, 19 (12) :2308-2310
[28]  
Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO
[29]  
2-5
[30]   C6-Modifications on chitosan to develop chitosan-based glycopolymers and their lectin-affinities with sigmoidal binding profiles [J].
Koshiji, Kazuhiro ;
Nonaka, Yuki ;
Iwamura, Maho ;
Dai, Fumiko ;
Matsuoka, Ryoji ;
Hasegawa, Teruaki .
CARBOHYDRATE POLYMERS, 2016, 137 :277-286