GRGDS-Functionalized Poly(lactide)-graft-poly(ethylene glycol) Copolymers: Combining Thiol-Ene Chemistry with Staudinger Ligation

被引:40
作者
Borchmann, Dorothee E.
ten Brummelhuis, Niels
Weck, Marcus [1 ]
机构
[1] NYU, Inst Mol Design, New York, NY 10003 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
AZIDE; CYCLOADDITION; NANOPARTICLES; POLYMERS;
D O I
10.1021/ma4005633
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 tri(ethylene glycol)-containing lactide analogue was synthesized via thiol-ene chemistry between a bifunctional triethylene glycol and allyl lactide. Subsequent tin octoate catalyzed ring opening polymerization yielded well poly(lactide)-graft-poly(ethylene glycol) copolymers with molecular weights of 6 x 10(3) g/mol and polydispersity indices of 1.6. The tri(ethylene glycol) chains along the copolymers contain azide termini that are capable of efficient postpolymerization functionalization. The utility of this strategy was demonstrated via successful Staudinger ligation to install the Gly-Arg-Gly-Asp-Ser (GRGDS) peptide.
引用
收藏
页码:4426 / 4431
页数:6
相关论文
共 29 条
  • [1] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems
    Agard, NJ
    Prescher, JA
    Bertozzi, CR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) : 15046 - 15047
  • [2] Development of thermal and photochemical strategies for thiol-ene click polymer functionalization
    Campos, Luis M.
    Killops, Kato L.
    Sakai, Ryosuke
    Paulusse, Jos M. J.
    Damiron, Denis
    Drockenmuller, Eric
    Messmore, Benjamin W.
    Hawker, Craig J.
    [J]. MACROMOLECULES, 2008, 41 (19) : 7063 - 7070
  • [3] Copper-Free Clickable Coatings
    Canalle, Luiz A.
    van Berkel, Sander S.
    de Haan, Laurens T.
    van Hest, Jan C. M.
    [J]. ADVANCED FUNCTIONAL MATERIALS, 2009, 19 (21) : 3464 - 3470
  • [4] Well-Defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side Chains
    Castillo, Jose A.
    Borchmann, Dorothee E.
    Cheng, Amy Y.
    Wang, Yufeng
    Hu, Chunhua
    Garcia, Andres J.
    Weck, Marcus
    [J]. MACROMOLECULES, 2012, 45 (01) : 62 - 69
  • [5] C-terminal site-specific PEGylation of a truncated thrombomodulin mutant with retention of full bioactivity
    Cazalis, CS
    Haller, CA
    Sease-Cargo, L
    Chaikof, EL
    [J]. BIOCONJUGATE CHEMISTRY, 2004, 15 (05) : 1005 - 1009
  • [6] Azide: A Unique Dipole for Metal-Free Bioorthogonal Ligations
    Debets, Marjoke F.
    van der Doelen, Christianus W. J.
    Rutjes, Floris P. J. T.
    van Delft, Floris L.
    [J]. CHEMBIOCHEM, 2010, 11 (09) : 1168 - 1184
  • [7] Degradable polyester scaffolds with controlled surface chemistry combining minimal protein adsorption with specific bioactivation
    Grafahrend, Dirk
    Heffels, Karl-Heinz
    Beer, Meike V.
    Gasteier, Peter
    Moeller, Martin
    Boehm, Gabriele
    Dalton, Paul D.
    Groll, Juergen
    [J]. NATURE MATERIALS, 2011, 10 (01) : 67 - 73
  • [8] Water-soluble thermoresponsive polylactides
    Jiang, Xuwei
    Smith, Milton R., III
    Baker, Gregory L.
    [J]. MACROMOLECULES, 2008, 41 (02) : 318 - 324
  • [9] Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation
    Kiick, KL
    Saxon, E
    Tirrell, DA
    Bertozzi, CR
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (01) : 19 - 24
  • [10] Poly(ethylene glycol) in Drug Delivery: Pros and Cons as Well as Potential Alternatives
    Knop, Katrin
    Hoogenboom, Richard
    Fischer, Dagmar
    Schubert, Ulrich S.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (36) : 6288 - 6308