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

Hong Y. Song, Mun H. Ngai, Zhen Y. Song, Paul A. MacAry, Jonathan Hobley, Martin J. Lear

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72 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3400-3406
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number17
DOIs
Publication statusPublished - 2009

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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