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

Jonas Bucevičius, Rūta Gerasimaitė, Kamila A. Kiszka, Shalini Pradhan, Georgij Kostiuk, Tanja Koenen and Gražvydas Lukinavičius ()
Additional contact information
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

Nature Communications, 2023, vol. 14, issue 1, 1-14

Abstract: 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.

Date: 2023
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-023-36913-2 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-36913-2

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-023-36913-2

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().