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  • Open Access

Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells

Authors

  • Jan Dommerholt,

    1. Radboud University Nijmegen, Institute for Molecules and Materials, Heijendaalseweg 135, 6525 AJ, Nijmegen (The Netherlands)
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    • These authors contributed equally to this work.

  • Samuel Schmidt,

    1. Radboud University Nijmegen, Nijmegen Center for Molecular Life Sciences, Department of Cell Biology, 6500 HB Nijmegen (The Netherlands)
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    • These authors contributed equally to this work.

  • Rinske Temming,

    1. Radboud University Nijmegen, Institute for Molecules and Materials, Heijendaalseweg 135, 6525 AJ, Nijmegen (The Netherlands)
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  • Linda J. A. Hendriks,

    1. Radboud University Nijmegen, Institute for Molecules and Materials, Heijendaalseweg 135, 6525 AJ, Nijmegen (The Netherlands)
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  • Floris P. J. T. Rutjes,

    1. Radboud University Nijmegen, Institute for Molecules and Materials, Heijendaalseweg 135, 6525 AJ, Nijmegen (The Netherlands)
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  • Jan C. M. van Hest,

    1. Radboud University Nijmegen, Institute for Molecules and Materials, Heijendaalseweg 135, 6525 AJ, Nijmegen (The Netherlands)
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  • Dirk J. Lefeber,

    1. Radboud University Medical Center, Department of Laboratory Medicine, 6525 ED Nijmegen (The Netherlands)
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  • Peter Friedl,

    1. Radboud University Nijmegen, Nijmegen Center for Molecular Life Sciences, Department of Cell Biology, 6500 HB Nijmegen (The Netherlands)
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  • Floris L. van Delft

    Corresponding author
    1. Radboud University Nijmegen, Institute for Molecules and Materials, Heijendaalseweg 135, 6525 AJ, Nijmegen (The Netherlands)
    • Radboud University Nijmegen, Institute for Molecules and Materials, Heijendaalseweg 135, 6525 AJ, Nijmegen (The Netherlands)
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  • This research has been financially supported (in part) by the Council for Chemical Sciences of The Netherlands Organization for Scientific Research (NWO-CW, to F.L.D). Dr. G. J. Boons (Complex Carbohydrate Research Center, Athens, GA) is kindly acknowledged for fruitful discussions.

Abstract

original image

Spannungslösend: Das leicht herstellbare, symmetrische Cycloalkin Bicyclo[6.1.0]non-4-in zeigt hervorragende Reaktionskinetiken bei spannungsgetriebenen Cycloadditionen mit Aziden und Nitronen (siehe Schema). In vitro wurden hoch spezifische Proteinmodifizierungen nachgewiesen. Zudem gelang mit subzellulärer Auflösung die Bildgebung der Glycanexpression in metastatischen Melanomzellen während der invasiven Migration in dreidimensionale Collagengitter.

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