Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells

Jan Dommerholt, Samuel Schmidt, Rinske Temming, L.J.A. Hendriks, F.P.J.T. Rutjes, J.C.M. Hest, van, D.J. Lefeber, Peter Friedl, F.L. van Delft

Research output: Contribution to journalArticleAcademicpeer-review

458 Citations (Scopus)

Abstract

I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are demonstrated in vitro and subcellular-resolved imaging of glycan expression was achieved in metastatic melanoma cells during invasive migration into three-dimensional collagen lattices.

Original languageEnglish
Pages (from-to)9422-9425
Number of pages4
JournalAngewandte Chemie - International Edition
Volume49
Issue number49
DOIs
Publication statusPublished - 3 Dec 2010
Externally publishedYes

Keywords

  • cycloadditions
  • cycloalkynes
  • imaging
  • kinetics
  • protein modification

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