Phosphine-mediated one-pot thiol-ene "click'' approach to polymer-protein conjugates

被引：102
作者：
Jones, Mathew W. [1 ]
Mantovani, Giuseppe [2 ]
Ryan, Sinead M. [3 ,4 ]
Wang, Xuexuan [3 ,4 ]
Brayden, David J. [3 ,4 ]
Haddleton, David M. [1 ]
机构：
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
[2] Univ Nottingham, Sch Pharm, Nottingham NG7 2RD, England
[3] Univ Coll Dublin, Sch Agr Food Sci & Vet Med, Dublin 4, Ireland
[4] Univ Coll Dublin, Conway Inst, Dublin 4, Ireland
来源：
CHEMICAL COMMUNICATIONS | 2009年 / 35期
基金：
爱尔兰科学基金会;
关键词：
SITE-SPECIFIC PEGYLATION; NATIVE DISULFIDE BONDS; THERAPEUTIC PROTEINS; ORTHOGONAL SYNTHESIS; CHEMISTRY; REDUCTION; EFFICIENT; DELIVERY; ROBUST; BRIDGE;
D O I：
10.1039/b906865a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We employ water-soluble organic phosphines as key reagents in a one-pot synthetic protocol where a (poly)peptide disulfide bridge is first reduced followed by subsequent reaction of the two thiols in situ with poly(monomethoxy ethylene glycol)-(meth) acrylates (p(mPEG)(M)A); we use salmon calcitonin (sCT) as a disulfide bridge-containing peptide, which contains a disulfide bridge-Cys1-Cys7-that can be reduced to give two sulfhydryl units available for thiol functionalisation; bioactivity is retained.
引用
收藏
页码：5272 / 5274
页数：3
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共 35 条
  • [1] Site-specific PEGylation of protein disulfide bonds using a three-carbon bridge
    Balan, Sibu
    Choi, Ji-won
    Godwin, Antony
    Teo, Ian
    Laborde, Carlos M.
    Heidelberger, Sibylle
    Zloh, Mire
    Shaunak, Sunil
    Brocchini, Steve
    [J]. BIOCONJUGATE CHEMISTRY, 2007, 18 (01) : 61 - 76
  • [2] Development of a tandem base-catalyzed, triphenylphosphine-mediated disulfide reduction-Michael addition
    Bartolozzi, Alessandra
    Foudoulakis, Hope M.
    Cole, Bridget M.
    [J]. SYNTHESIS-STUTTGART, 2008, (13): : 2023 - 2032
  • [3] Cysteine-reactive polymers synthesized by atom transfer radical polymerization for conjugation to proteins
    Bontempo, D
    Heredia, KL
    Fish, BA
    Maynard, HD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) : 15372 - 15373
  • [4] Efficient Usage of Thiocarbonates for Both the Production and the Biofunctionalization of Polymers
    Boyer, Cyrille
    Bulmus, Volga
    Davis, Thomas P.
    [J]. MACROMOLECULAR RAPID COMMUNICATIONS, 2009, 30 (07) : 493 - 497
  • [5] Disulfide bridge based PEGylation of proteins
    Brocchini, Steve
    Godwin, Antony
    Balan, Sibu
    Choi, Ji-won
    Zloh, Mire
    Shaunak, Sunil
    [J]. ADVANCED DRUG DELIVERY REVIEWS, 2008, 60 (01) : 3 - 12
  • [6] PEGylation of native disulfide bonds in proteins
    Brocchini, Steve
    Balan, Sibu
    Godwin, Antony
    Choi, Ji-Won
    Zloh, Mire
    Shaunak, Sunil
    [J]. NATURE PROTOCOLS, 2006, 1 (05) : 2241 - 2252
  • [7] SELECTIVE REDUCTION OF DISULFIDES BY TRIS(2-CARBOXYETHYL)PHOSPHINE
    BURNS, JA
    BUTLER, JC
    MORAN, J
    WHITESIDES, GM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) : 2648 - 2650
  • [8] Highly Versatile and Robust Materials for Soft Imprint Lithography Based on Thiol-ene Click Chemistry
    Campos, Luis M.
    Meinel, Ines
    Guino, Rosette G.
    Schierhorn, Martin
    Gupta, Nalini
    Stucky, Galen D.
    Hawker, Craig J.
    [J]. ADVANCED MATERIALS, 2008, 20 (19) : 3728 - +
  • [9] Convergent synthesis of 3-arm star polymers from RAFT-prepared poly(N,N-diethylacrylamide) via a thiol-ene click reaction
    Chan, Justin W.
    Yu, Bing
    Hoyle, Charles E.
    Lowe, Andrew B.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (40) : 4959 - 4961
  • [10] Photopolymerization of Thiol-Alkynes: Polysulfide Networks
    Chan, Justin W.
    Zhou, Hui
    Hoyle, Charles E.
    Lowe, Andrew B.
    [J]. CHEMISTRY OF MATERIALS, 2009, 21 (08) : 1579 - 1585
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