Direct synthesis of well-defined heterotelechelic polymers for bioconjugations

被引：132

作者：

Boyer, Cyrille ^{[1
]}

Liu, Jingquan ^{[1
]}

Bulmus, Volga ^{[1
]}

Davis, Thomas P. ^{[1
]}

Barner-Kowollik, Christopher ^{[1
]}

Stenzel, Martina H. ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem Sci & Engn, CAMD, Sydney, NSW 2052, Australia

来源：

MACROMOLECULES | 2008年 / 41卷 / 15期

关键词：

D O I：

10.1021/ma800289u

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Direct synthesis of well-defined heterotelechelic polymers having functional groups allowing the chemoselective bioconjugations would be desirable to enhance the versatility of polymers for bioconjugations and bio-related applications. Considering this, well-defined alpha-azide, omega-dithiopyridine polymers were synthesized in one step via the reversible addition-fragmentation chain transfer (RAFT) polymerization. The telechelic functionality (i.e., mole ratio of the omega-dithiopyridine to the alpha-azide end group) of polymers was above 0.90, indicating the efficient generation of well-defined heterotelechelic polymers. The heterotelechelic functionality for chemoselective bioconjugations was tested by reacting alpha-azide, omega-dithiopyridine poly(NIPAAm) with model biomolecules, i.e., biotin/avidin, glutathione, and bovine serum albumin, via click and thiol-disulfide exchange chemistries. Near-stoichiometric conjugation with biomolecules indicated high functionality of the polymer end groups.

引用

页码：5641 / 5650

页数：10

共 72 条

[1] Complex macromolecular architectures by reversible addition fragmentation chain transfer chemistry: Theory and practice [J].

Barner, Leonie ;

Davis, Thomas P. ;

Stenzel, Martina H. ;

Barner-Kowollik, Christopher .

MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (05) :539-559

[2] Versatile precursors of functional RAFT agents. Application to the synthesis of bio-related end-functionalized polymers [J].

Bathfield, M ;

D'Agosto, F ;

Spitz, R ;

Charreyre, MT ;

Delair, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2546-2547

[3] One-step synthesis of low polydispersity, biotinylated poly(N-isopropylacrylamide) by ATRP [J].

Bontempo, D ;

Li, RC ;

Ly, T ;

Brubaker, CE ;

Maynard, HD .

CHEMICAL COMMUNICATIONS, 2005, (37) :4702-4704

[4] Cysteine-reactive polymers synthesized by atom transfer radical polymerization for conjugation to proteins [J].

Bontempo, D ;

Heredia, KL ;

Fish, BA ;

Maynard, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15372-15373

[5] Telechelic oligomers and macromonomers by radical techniques [J].

Boutevin, B. ;

David, G. ;

Boyer, C. .

OLIGOMERS POLYMER COMPOSTIES MOLECULAR IMPRINTING, 2007, 206 (31-135) :31-135

[6]

BOUTEVIN B, 2007, MACROMOLECULAR ENG, V2

[7] Well-defined protein-polymer conjugates via in situ RAFT polymerization [J].

Boyer, Cyrille ;

Bulmus, Volga ;

Liu, Jingquan ;

Davis, Thomas P. ;

Stenzel, Martina H. ;

Barner-Kowollik, Christopher .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (22) :7145-7154

[8] Direct synthesis of thermally responsive DMA/NIPAM diblock and DMA/NIPAM/DMA triblock copolymers via aqueous, room temperature RAFT polymerization [J].

Convertine, AJ ;

Lokitz, BS ;

Vasileva, Y ;

Myrick, LJ ;

Scales, CW ;

Lowe, AB ;

McCormick, CL .

MACROMOLECULES, 2006, 39 (05) :1724-1730

[9] Folate-conjugated thermoresponsive block copolymers: Highly efficient conjugation and solution self-assembly [J].

De, Priyadarsi ;

Gondi, Sudershan R. ;

Sumerlin, Brent S. .

BIOMACROMOLECULES, 2008, 9 (03) :1064-1070

[10] Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae [J].

Deiters, A ;

Cropp, TA ;

Mukherji, M ;

Chin, JW ;

Anderson, JC ;

Schultz, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11782-11783

← 1 2 3 4 5 6 7 8 →