Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides

Song, Hong Y. and Ngai, Mun H. and Song, Zhen Y. and MacAry, Paul A. and Hobley, Jonathan and Lear, Martin J. (2009) Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides. Organic & Biomolecular Chemistry, 7 (17). pp. 3400-3406. ISSN 1477-0520

Full content URL: http://dx.doi.org/10.1039/b904060a

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Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides

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Abstract

The cellular tracking, detection and sensing of protein or antibody movement are important aspects to advance our understanding of biomolecular interactions and activity. Antibodies modified with fluorescent dyes are also valuable tools, especially in immunology research. We describe here a proof-of-principle study of a new water-soluble coumarin probe with a maleimide thiol-reacting unit to fluorescently tag biomolecules. Highlights include: (1) a convenient water-based preparation of N-substituted maleimides, (2) a one-pot preparation of activated maleimido-esters, and (3) a bio-conjugation protocol for the selenol-promoted reduction of native disulfide bonds and the ‘site-specific’ labelling of antibodies with no significant loss of activity.

Keywords:Fluorescent-labeled probes, Antibody labelling, Maleimide reagents
Subjects:F Physical Sciences > F165 Biomolecular Chemistry
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F163 Bio-organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:17115
Deposited On:17 Apr 2015 10:16

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