In Situ Conjugation of Dithiophenol Maleimide Polymers and Oxytocin for Stable and Reversible Polymer-Peptide Conjugates

被引：45
作者：
Collins, Jennifer [1 ]
Tanaka, Joji [1 ]
Wilson, Paul [1 ,2 ]
Kempe, Kristian [1 ]
Davis, Thomas P. [1 ,2 ]
McIntosh, Michelle P. [2 ]
Whittaker, Michael R. [2 ]
Haddleton, David M. [1 ,2 ]
机构：
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
[2] Monash Univ, Monash Inst Pharmaceut Sci, ARC Ctr Excellence Convergent Bionano Sci & Techn, Parkville, Vic 3052, Australia
来源：
BIOCONJUGATE CHEMISTRY | 2015年 / 26卷 / 04期
基金：
英国工程与自然科学研究理事会; 澳大利亚研究理事会;
关键词：
DIVALENT METAL-IONS; DRUG-DELIVERY; STABILIZE OXYTOCIN; AQUEOUS-SOLUTION; DISULFIDE BONDS; PEGYLATION; BIOCONJUGATION; PROTEINS; BUFFER; BROMOMALEIMIDES;
D O I：
10.1021/bc5006202
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
The in situ one-pot synthesis of peptidepolymer bioconjugates is reported. Conjugation occurs efficiently without the need for purification of dithiophenol maleimide functionalized polymer as a disulfide bridging agent for the therapeutic oxytocin. Conjugation of polymers was demonstrated to be reversible and to significantly improve the solution stability of oxytocin.
引用
收藏
页码：633 / 638
页数：6
相关论文
共 54 条
  • [1] Anderson ME, 1998, CHEM-BIOL INTERACT, V112, P1
  • [2] The formation of oxytocin dimers is suppressed by the zinc-aspartate-oxytocin complex
    Avanti, Christina
    Hinrichs, Wouter L. J.
    Casini, Angela
    Eissens, Anko C.
    Van Dam, Annie
    Kedrov, Alexej
    Driessen, Arnold J. M.
    Frijlink, Henderik W.
    Permentier, Hjalmar P.
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 2013, 102 (06) : 1734 - 1741
  • [3] Aspartate buffer and divalent metal ions affect oxytocin in aqueous solution and protect it from degradation
    Avanti, Christina
    Oktaviani, Nur Alia
    Hinrichs, Wouter L. J.
    Frijlink, Henderik W.
    Mulder, Frans A. A.
    [J]. INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2013, 444 (1-2) : 139 - 145
  • [4] A New Strategy To Stabilize Oxytocin in Aqueous Solutions: II. Suppression of Cysteine-Mediated Intermolecular Reactions by a Combination of Divalent Metal Ions and Citrate
    Avanti, Christina
    Permentier, Hjalmar P.
    van Dam, Annie
    Poole, Robert
    Jiskoot, Wim
    Frijlink, Henderik W.
    Hinrichs, Wouter L. J.
    [J]. MOLECULAR PHARMACEUTICS, 2012, 9 (03) : 554 - 562
  • [5] A New Strategy to Stabilize Oxytocin in Aqueous Solutions: I. The Effects of Divalent Metal Ions and Citrate Buffer
    Avanti, Christina
    Amorij, Jean-Pierre
    Setyaningsih, Dewi
    Hawe, Andrea
    Jiskoot, Wim
    Visser, Jan
    Kedrov, Alexej
    Driessen, Arnold J. M.
    Hinrichs, Wouter L. J.
    Frijlink, Henderik W.
    [J]. AAPS JOURNAL, 2011, 13 (02): : 284 - 290
  • [6] 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
  • [7] SOME PHARMACOLOGICAL ACTIONS OF 4 SYNTHETIC ANALOGUES OF OXYTOCIN
    BERDE, B
    DOEPFNER, W
    KONZETT, H
    [J]. BRITISH JOURNAL OF PHARMACOLOGY AND CHEMOTHERAPY, 1957, 12 (02): : 209 - 214
  • [8] 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
  • [9] Emerging synthetic approaches for protein-polymer conjugations
    Broyer, Rebecca M.
    Grover, Gregory N.
    Maynard, Heather D.
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (08) : 2212 - 2226
  • [10] A mild synthesis of N-functionalised bromomaleimides, thiomaleimides and bromopyridazinediones
    Castaneda, Lourdes
    Wright, Zoe V. F.
    Marculescu, Cristina
    Tran, Trang M.
    Chudasama, Vijay
    Maruani, Antoine
    Hull, Elizabeth A.
    Nunes, Joao P. M.
    Fitzmaurice, Richard J.
    Smith, Mark E. B.
    Jones, Lyn H.
    Caddick, Stephen
    Baker, James R.
    [J]. TETRAHEDRON LETTERS, 2013, 54 (27) : 3493 - 3495
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