Michael-type addition as a tool for surface functionalization

Martin Heggli, Nicola Tirelli, Andreas Zisch, Jeffrey A. Hubbell

Research output: Contribution to journalArticle

49 Scopus citations

Abstract

Michael-type addition (conjugate addition reaction between electron-poor olefins and nucleophiles, such as thiols) has been successfully used as a convenient tool for surface functionalization. Due to its mild character, this method is potentially useful for the introduction of sensitive groups, which can provide bioactivity and targeting possibilities to surfaces of, for example, colloidal carriers. As reaction partners, in our study we have used thiols, possibly present in peptidic structures, and acrylates, at the end of protein-repellant PEG chains. Satisfactory results were obtained with thiols in solution and acrylic groups bound to the surface. Alternatively, the use of thiols on the particles, even if generated in situ, did not provide useful results.

Original languageEnglish (US)
Pages (from-to)967-973
Number of pages7
JournalBioconjugate Chemistry
Volume14
Issue number5
DOIs
StatePublished - Sep 1 2003

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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    Heggli, M., Tirelli, N., Zisch, A., & Hubbell, J. A. (2003). Michael-type addition as a tool for surface functionalization. Bioconjugate Chemistry, 14(5), 967-973. https://doi.org/10.1021/bc0340621