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A general highly efficient synthesis of biocompatible rhodamine dyes and probes for live-cell multicolor nanoscopy

Author

Listed:
  • Jonas Bucevičius

    (Max Planck Institute for Multidisciplinary Sciences)

  • Rūta Gerasimaitė

    (Max Planck Institute for Multidisciplinary Sciences)

  • Kamila A. Kiszka

    (Max Planck Institute for Multidisciplinary Sciences)

  • Shalini Pradhan

    (Max Planck Institute for Multidisciplinary Sciences)

  • Georgij Kostiuk

    (Max Planck Institute for Multidisciplinary Sciences)

  • Tanja Koenen

    (Max Planck Institute for Multidisciplinary Sciences)

  • Gražvydas Lukinavičius

    (Max Planck Institute for Multidisciplinary Sciences)

Abstract

The development of live-cell fluorescence nanoscopy is powered by the availability of suitable fluorescent probes. Rhodamines are among the best fluorophores for labeling intracellular structures. Isomeric tuning is a powerful method for optimizing the biocompatibility of rhodamine-containing probes without affecting their spectral properties. An efficient synthesis pathway for 4-carboxyrhodamines is still lacking. We present a facile protecting-group-free 4-carboxyrhodamines’ synthesis based on the nucleophilic addition of lithium dicarboxybenzenide to the corresponding xanthone. This approach drastically reduces the number of synthesis steps, expands the achievable structural diversity, increases overall yields and permits gram-scale synthesis of the dyes. We synthesize a wide range of symmetrical and unsymmetrical 4-carboxyrhodamines covering the whole visible spectrum and target them to multiple structures in living cells – microtubules, DNA, actin, mitochondria, lysosomes, Halo-tagged and SNAP-tagged proteins. The enhanced permeability fluorescent probes operate at submicromolar concentrations, allowing high-contrast STED and confocal microscopy of living cells and tissues.

Suggested Citation

  • Jonas Bucevičius & Rūta Gerasimaitė & Kamila A. Kiszka & Shalini Pradhan & Georgij Kostiuk & Tanja Koenen & Gražvydas Lukinavičius, 2023. "A general highly efficient synthesis of biocompatible rhodamine dyes and probes for live-cell multicolor nanoscopy," Nature Communications, Nature, vol. 14(1), pages 1-14, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-36913-2
    DOI: 10.1038/s41467-023-36913-2
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