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
相关论文
共 35 条
  • [21] Synthesis of protein-polymer conjugates
    Heredia, Karina L.
    Maynard, Heather D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) : 45 - 53
  • [22] Thiol-enes: Chemistry of the past with promise for the future
    Hoyle, CE
    Lee, TY
    Roper, T
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (21) : 5301 - 5338
  • [23] Synthesis, Characterization and Cleavage of Surface-Bound Linear Polymers Formed Using Thiol-Ene Photopolymerizations
    Khire, Vaibhav S.
    Lee, Tai Yeon
    Bowman, Christopher N.
    [J]. MACROMOLECULES, 2008, 41 (20) : 7440 - 7447
  • [24] Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "Click" chemistry
    Killops, Kato L.
    Campos, Luis M.
    Hawker, Craig J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) : 5062 - +
  • [25] Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO
  • [26] 2-X
  • [27] Isolation, characterization, and stability of positional isomers of mono-PEGylated salmon calcitonins
    Lee, KC
    Moon, SC
    Park, MO
    Lee, JT
    Na, DH
    Yoo, SD
    Lee, HS
    DeLuca, PP
    [J]. PHARMACEUTICAL RESEARCH, 1999, 16 (06) : 813 - 818
  • [28] Thiol-allyl ether-methacrylate ternary systems. Polymerization mechanism
    Lee, Tai Yeon
    Smith, Zachary
    Reddy, Sirish K.
    Cramer, Neil B.
    Bowman, Christopher N.
    [J]. MACROMOLECULES, 2007, 40 (05) : 1466 - 1472
  • [29] Polymer-drug conjugation, recent achievements and general strategies
    Pasut, G.
    Veronese, F. M.
    [J]. PROGRESS IN POLYMER SCIENCE, 2007, 32 (8-9) : 933 - 961
  • [30] Metal free thiol-maleimide 'Click' reaction as a mild functionalisation strategy for degradable polymers
    Pounder, Ryan J.
    Stanford, Matthew J.
    Brooks, Paul
    Richards, Stephen P.
    Dove, Andrew P.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (41) : 5158 - 5160
1234