A phospha-oseltamivir-biotin conjugate as a strong and selective adhesive for the influenza virus

被引：5
作者：
Streicher, Hansjoerg [1 ]
Martin, Stephen R. [2 ]
Coombs, Peter J. [2 ]
McCauley, John [3 ]
Neill-Hall, David [1 ]
Stanley, Mathew [1 ]
机构：
[1] Univ Sussex, Sch Life Sci, Div Chem, Brighton BN1 9QJ, E Sussex, England
[2] MRC Natl Inst Med Res, Div Phys Biochem, London NW7 1AA, England
[3] MRC Natl Inst Med Res, Div Virol, London NW7 1AA, England
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 07期
基金：
英国医学研究理事会;
关键词：
Influenza virus; Oseltamivir; Neuraminidase inhibitor; Biosensors; Virus immobilisation; RECEPTOR-BINDING; A VIRUSES; NEURAMINIDASE; HEMAGGLUTININS;
D O I：
10.1016/j.bmcl.2014.02.021
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
We present the synthesis and application of a molecule containing both the powerful influenza neuraminidase (NA) inhibitor phospha-oseltamivir and D-biotin, connected via an undecaethylene glycol spacer. It inhibits influenza virus neuraminidase (from the H3N2 X31 virus) in the same range as oseltamivir, with a slow off-rate, and produces a stable NA-coated surface when loaded onto streptavidin-coated biosensors. Purified X31 virus binds to these loaded biosensors with an apparent dissociation constant in the low picomolar range and binding of antibodies to the immobilized virus could be readily detected. The compound is thus a potential candidate for the selective immobilization of influenza virus in influenza diagnosis, vaccine choice, development or testing. (c) 2014 The Authors. Published by Elsevier Ltd.
引用
收藏
页码：1805 / 1807
页数：3
相关论文
共 12 条
  • [1] Efficient Synthesis of Highly Active Phospha-Isosteres of the Influenza Neuraminidase Inhibitor Oseltamivir
    Carbain, Benoit
    Collins, Patrick J.
    Callum, Lori
    Martin, Stephen R.
    Hay, Alan J.
    McCauley, John
    Streicher, Hansjoerg
    [J]. CHEMMEDCHEM, 2009, 4 (03) : 335 - 337
  • [2] Crystal structures of oseltamivir-resistant influenza virus neuraminidase mutants
    Collins, Patrick J.
    Haire, Lesley F.
    Lin, Yi Pu
    Liu, Junfeng
    Russell, Rupert J.
    Walker, Philip A.
    Skehel, John J.
    Martin, Stephen R.
    Hay, Alan J.
    Gamblin, Steven J.
    [J]. NATURE, 2008, 453 (7199) : 1258 - U61
  • [3] ANTIGENIC ANALYSES OF INFLUENZA-VIRUS HEMAGGLUTININS WITH DIFFERENT RECEPTOR-BINDING SPECIFICITIES
    DANIELS, RS
    DOUGLAS, AR
    SKEHEL, JJ
    WILEY, DC
    NAEVE, CW
    WEBSTER, RG
    ROGERS, GN
    PAULSON, JC
    [J]. VIROLOGY, 1984, 138 (01) : 174 - 177
  • [4] The annual production cycle for influenza vaccine
    Gerdil, C
    [J]. VACCINE, 2003, 21 (16) : 1776 - 1779
  • [5] Detection of intact influenza viruses using biotinylated biantennary S-sialosides
    Kale, Ramesh R.
    Mukundan, Harshini
    Price, Dominique N.
    Harris, J. Foster
    Lewallen, Daniel M.
    Swanson, Basil I.
    Schmidt, Jurgen G.
    Lyer, Suri S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (26) : 8169 - +
  • [6] Evolution of the receptor binding properties of the influenza A(H3N2) hemagglutinin
    Lin, Yi Pu
    Xiong, Xiaoli
    Wharton, Stephen A.
    Martin, Stephen R.
    Coombs, Peter J.
    Vachieri, Sebastien G.
    Christodoulou, Evangelos
    Walker, Philip A.
    Liu, Junfeng
    Skehel, John J.
    Gamblin, Steven J.
    Hay, Alan J.
    Daniels, Rodney S.
    McCauley, John W.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (52) : 21474 - 21479
  • [7] Neuraminidase Receptor Binding Variants of Human Influenza A(H3N2) Viruses Resulting from Substitution of Aspartic Acid 151 in the Catalytic Site: a Role in Virus Attachment?
    Lin, Yi Pu
    Gregory, Victoria
    Collins, Patrick
    Kloess, Johannes
    Wharton, Stephen
    Cattle, Nicholas
    Lackenby, Angie
    Daniels, Rodney
    Hay, Alan
    [J]. JOURNAL OF VIROLOGY, 2010, 84 (13) : 6769 - 6781
  • [8] Tethered neuraminidase inhibitors that bind an influenza virus: A first step towards a diagnostic method for influenza
    McKimm-Breschkin, JL
    Colman, PM
    Jin, B
    Krippner, GY
    McDonald, M
    Reece, PA
    Tucker, SP
    Waddington, L
    Watson, KG
    Wu, WY
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (27) : 3118 - 3121
  • [9] Ndiofon W., 2011, VIRUSES, V5, P206
  • [10] Avian and human receptor binding by hemagglutinins of influenza A viruses
    Russell, RJ
    Stevens, DJ
    Haire, LF
    Gamblin, SJ
    Skehel, JJ
    [J]. GLYCOCONJUGATE JOURNAL, 2006, 23 (1-2) : 85 - 92
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