A simple and versatile design concept for fluorophore derivatives with intramolecular photostabilization

Jasper H. M. van der Velde, Jens Oelerich, Jingyi Huang, Jochem H. Smit, Atieh Aminian Jazi, Silvia Galiani, Kirill Kolmakov, Giorgos Gouridis, Christian Eggeling, Andreas Herrmann, Gerard Roelfes and Thorben Cordes ()
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Jasper H. M. van der Velde: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen
Jens Oelerich: Stratingh Institute for Chemistry, University of Groningen
Jingyi Huang: Zernike Institute for Advanced Materials, University of Groningen
Jochem H. Smit: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen
Atieh Aminian Jazi: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen
Silvia Galiani: MRC Human Immunology Unit, Weatherall Institute of Molecular Medicine, University of Oxford
Kirill Kolmakov: Max-Planck-Institute of Molecular Medicine
Giorgos Gouridis: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen
Christian Eggeling: MRC Human Immunology Unit, Weatherall Institute of Molecular Medicine, University of Oxford
Andreas Herrmann: Zernike Institute for Advanced Materials, University of Groningen
Gerard Roelfes: Stratingh Institute for Chemistry, University of Groningen
Thorben Cordes: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen

Nature Communications, 2016, vol. 7, issue 1, 1-17

Abstract: Abstract Intramolecular photostabilization via triple-state quenching was recently revived as a tool to impart synthetic organic fluorophores with ‘self-healing’ properties. To date, utilization of such fluorophore derivatives is rare due to their elaborate multi-step synthesis. Here we present a general strategy to covalently link a synthetic organic fluorophore simultaneously to a photostabilizer and biomolecular target via unnatural amino acids. The modular approach uses commercially available starting materials and simple chemical transformations. The resulting photostabilizer–dye conjugates are based on rhodamines, carbopyronines and cyanines with excellent photophysical properties, that is, high photostability and minimal signal fluctuations. Their versatile use is demonstrated by single-step labelling of DNA, antibodies and proteins, as well as applications in single-molecule and super-resolution fluorescence microscopy. We are convinced that the presented scaffolding strategy and the improved characteristics of the conjugates in applications will trigger the broader use of intramolecular photostabilization and help to emerge this approach as a new gold standard.

Date: 2016
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DOI: 10.1038/ncomms10144

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