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Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED
Author(s) -
Butkevich Alexey N.,
Belov Vladimir N.,
Kolmakov Kirill,
Sokolov Viktor V.,
Shojaei Heydar,
Sidenstein Sven C.,
Kamin Dirk,
Matthias Jessica,
Vlijm Rifka,
Engelhardt Johann,
Hell Stefan W.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701216
Subject(s) - sted microscopy , fluorescence , chemistry , in silico , zwitterion , absorption (acoustics) , resolution (logic) , heteroatom , stimulated emission , molecule , biochemistry , ring (chemistry) , materials science , organic chemistry , optics , laser , physics , artificial intelligence , computer science , gene , composite material
Hydroxylated rhodamines, carbopyronines, silico‐ and germanorhodamines with absorption maxima in the range of 530–640 nm were prepared and applied in specific labeling of living cells. The direct and high‐yielding entry to germa‐ and silaxanthones tolerates the presence of protected heteroatoms and may be considered for the syntheses of various sila‐ and germafluoresceins, as well as ‐rhodols. Application in stimulated emission depletion (STED) fluorescence microscopy revealed a resolution of 50–75 nm in one‐ and two‐color imaging of vimentin‐HaloTag fused protein and native tubulin. The established structure–property relationships allow for prediction of the spectral properties and the positions of spirolactone/zwitterion equilibria for the new analogues of rhodamines, carbo‐, silico‐, and germanorhodamines using simple additive schemes.