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
来源：
MACROMOLECULES | 2013年 / 46卷 / 11期
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
  • [11] Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO
  • [12] 2-X
  • [13] Synthesis of Poly(ethylene glycol)/Polypeptide/Poly(D,L-lactide) Copolymers and Their Nanoparticles
    Lee, Hyunpyo
    Park, Jun Beum
    Chang, Ji Young
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (13) : 2859 - 2865
  • [14] Synthesis and characterization of allyl functionalized poly(α-hydroxy)acids and their further dihydroxylation and epoxidation
    Leemhuis, Mark
    Akeroyd, Niels
    Kruijtzer, John A. W.
    van Nostrum, Cornelus F.
    Hennink, Wim E.
    [J]. EUROPEAN POLYMER JOURNAL, 2008, 44 (02) : 308 - 317
  • [15] Biodegradable polymers applied in tissue engineering research: a review
    Martina, Monique
    Hutmacher, Dietmar W.
    [J]. POLYMER INTERNATIONAL, 2007, 56 (02) : 145 - 157
  • [16] Staudinger ligation: A peptide from a thioester and azide
    Nilsson, BL
    Kiessling, LL
    Raines, RT
    [J]. ORGANIC LETTERS, 2000, 2 (13) : 1939 - 1941
  • [17] Strain-Promoted Alkyne Azide Cycloaddition for the Functionalization of Poly(amide)-Based Dendrons and Dendrimers
    Ornelas, Catia
    Broichhagen, Johannes
    Weck, Marcus
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) : 3923 - 3931
  • [18] Targeting of polyamidoamine-DNA nanoparticles using the Staudinger ligation: Attachment of an RGD motif either before or after complexation
    Parkhouse, Susan M.
    Garnett, Martin C.
    Chan, Weng C.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (13) : 6641 - 6650
  • [19] Combining RAFT and Staudinger Ligation: A Potentially New Synthetic Tool for Bioconjugate Formation
    Poetzsch, Robert
    Fleischmann, Sven
    Tock, Christian
    Komber, Hartmut
    Voit, Brigitte I.
    [J]. MACROMOLECULES, 2011, 44 (09) : 3260 - 3269
  • [20] ARG-GLY-ASP - A VERSATILE CELL RECOGNITION SIGNAL
    RUOSLAHTI, E
    PIERSCHBACHER, MD
    [J]. CELL, 1986, 44 (04) : 517 - 518
123