Michael-type addition as a tool for surface functionalization

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

Research output: Contribution to journalArticle

48 Citations (Scopus)

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

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Sulfhydryl Compounds
Nucleophiles
Addition reactions
Acrylates
Bioactivity
Polyethylene glycols
Olefins
Acrylics
Alkenes
Proteins
Electrons

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

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

Michael-type addition as a tool for surface functionalization. / Heggli, Martin; Tirelli, Nicola; Zisch, Andreas; Hubbell, Jeffrey A.

In: Bioconjugate Chemistry, Vol. 14, No. 5, 01.09.2003, p. 967-973.

Research output: Contribution to journalArticle

Heggli, M, Tirelli, N, Zisch, A & Hubbell, JA 2003, 'Michael-type addition as a tool for surface functionalization', Bioconjugate Chemistry, vol. 14, no. 5, pp. 967-973. https://doi.org/10.1021/bc0340621
Heggli, Martin ; Tirelli, Nicola ; Zisch, Andreas ; Hubbell, Jeffrey A. / Michael-type addition as a tool for surface functionalization. In: Bioconjugate Chemistry. 2003 ; Vol. 14, No. 5. pp. 967-973.
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