Cargando…

Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED

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...

Descripción completa

Detalles Bibliográficos
Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5599963/
https://www.ncbi.nlm.nih.gov/pubmed/28370443
http://dx.doi.org/10.1002/chem.201701216
_version_ 1783264157661921280
author 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.
author_facet 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.
author_sort Butkevich, Alexey N.
collection PubMed
description 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.
format Online
Article
Text
id pubmed-5599963
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-55999632017-10-02 Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED 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. Chemistry Communications 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. John Wiley and Sons Inc. 2017-05-02 2017-09-07 /pmc/articles/PMC5599963/ /pubmed/28370443 http://dx.doi.org/10.1002/chem.201701216 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
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.
Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED
title Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED
title_full Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED
title_fullStr Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED
title_full_unstemmed Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED
title_short Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED
title_sort hydroxylated fluorescent dyes for live‐cell labeling: synthesis, spectra and super‐resolution sted
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5599963/
https://www.ncbi.nlm.nih.gov/pubmed/28370443
http://dx.doi.org/10.1002/chem.201701216
work_keys_str_mv AT butkevichalexeyn hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT belovvladimirn hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT kolmakovkirill hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT sokolovviktorv hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT shojaeiheydar hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT sidensteinsvenc hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT kamindirk hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT matthiasjessica hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT vlijmrifka hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT engelhardtjohann hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted
AT hellstefanw hydroxylatedfluorescentdyesforlivecelllabelingsynthesisspectraandsuperresolutionsted