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

Abstract 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.

• Publication year

  2017

• Venue

  Chemistry

• Publication date

  2017-05-02

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1002/chem.201701216PMID 28370443PMCID 5599963
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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

  2017cited by this paper
• Fluorogenic Probes for Multicolor Imaging in Living Cells.

  2016cited by this paper
• Multicolour Multilevel STED nanoscopy of Actin/Spectrin Organization at Synapses

  2016cited by this paper
• "Reduced" Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy.

  2016cited by this paper
• Labeling proteins inside living cells using external fluorophores for microscopy

  2016cited by this paper
• Two-colour live-cell nanoscale imaging of intracellular targets

  2016cited by this paper
• Discovery and Mechanism of Highly Efficient Cyclic Cell-Penetrating Peptides.

  2016cited by this paper
• Fluorescent Rhodamines and Fluorogenic Carbopyronines for Super‐Resolution STED Microscopy in Living Cells

  2016cited by this paper
• Fluoreszierende Rhodamine und fluorogene Carbopyronine für die STED‐Mikroskopie lebender Zellen

  2016cited by this paper
• Stimulated Emission Depletion Nanoscopy Reveals Time-Course of Human Immunodeficiency Virus Proteolytic Maturation.

  2016cited by this paper
• Silicon-substituted xanthene dyes and their applications in bioimaging.

  2015cited by this paper
• Analysis of chemical equilibrium of silicon-substituted fluorescein and its application to develop a scaffold for red fluorescent probes.

  2015cited by this paper
• Fluorogenic probes for live-cell imaging of the cytoskeleton

  2014cited by this paper
• A general method to improve fluorophores for live-cell and single-molecule microscopy

  2014cited by this paper
• Hydrophobic Fluorescent Probes Introduce Artifacts into Single Molecule Tracking Experiments Due to Non-Specific Binding

  2013cited by this paper
• pH-dependent Si-fluorescein hypochlorous acid fluorescent probe: spirocycle ring-opening and excess hypochlorous acid-induced chlorination.

  2013cited by this paper
• Red fluorescent probe for monitoring the dynamics of cytoplasmic calcium ions.

  2013cited by this paper
• A near-infrared fluorophore for live-cell super-resolution microscopy of cellular proteins.

  2013cited by this paper
• Predicting the UV–vis spectra of oxazine dyes

  2011cited by this paper
• Evolution of group 14 rhodamines as platforms for near-infrared fluorescence probes utilizing photoinduced electron transfer.

  2011cited by this paper
• Development of a fluorescein analogue, TokyoMagenta, as a novel scaffold for fluorescence probes in red region.

  2011cited by this paper
• How to obtain labeled proteins and what to do with them.

  2010cited by this paper
• Stimulated emission depletion nanoscopy of living cells using SNAP-tag fusion proteins.

  2010cited by this paper
• An engineered protein tag for multiprotein labeling in living cells.

  2008cited by this paper
• Photostable, amino reactive and water-soluble fluorescent labels based on sulfonated rhodamine with a rigidized xanthene fragment.

  2008cited by this paper
• HaloTag: a novel protein labeling technology for cell imaging and protein analysis.

  2008cited by this paper
• Cell-penetrating Peptides

  2003cited by this paper
• Different mechanisms for cellular internalization of the HIV-1 Tat-derived cell penetrating peptide and recombinant proteins fused to Tat.

  2002cited by this paper

• Oxone®-mediated Dakin-like reaction to synthesize hydroxyarenes: an approach using pyrazolo[1,5-a]pyrimidines

  2025cites this paper
• A General Strategy to Fine‐Tune Group 14 Rhodamines for Ultrahigh Signal‐to‐Noise Ratio Labeling In Vivo by Nano‐Aggregation

  2025cites this paper
• Dibutylated Si-fluorescein: enhanced hydrophobicity for fluorogenic labeling in vivo.

  2025cites this paper
• Asymmetric Donor–Acceptor 2,7-Disubstituted Fluorenes and Their 9-Diazoderivatives: Synthesis, Optical Spectra and Photolysis

  2025influential citation
• Synthetic fluorophores for live-cell fluorescence microscopy and biosensing

  2025cites this paper
• Xanthene, cyanine, oxazine and BODIPY: the four pillars of the fluorophore empire for super-resolution bioimaging.

  2023cites this paper
• A machine-learning tool to predict substrate-adaptive conditions for Pd-catalyzed C–N couplings

  2023cites this paper
• Photoactivatable Carbo- and Silicon-Rhodamines and Their Application in MINFLUX Nanoscopy.

  2023cites this paper
• Germanium- and tin-bridged diazulenylmethyl cations: effects of group 14 elements on the structure and properties of π-extended cations.

  2023cites this paper
• Fluoroalkylations and Fluoroalkenylations with Iodonium Salts

  2023cites this paper
• A Bright Surprise: Live‐Cell Labeling with Negatively Charged Fluorescent Probes based on Disulfonated Rhodamines and HaloTag

  2023cites this paper
• Fluorescence-based super-resolution-microscopy strategies for chromatin studies

  2023cites this paper
• A general highly efficient synthesis of biocompatible rhodamine dyes and probes for live-cell multicolor nanoscopy

  2023cites this paper
• HaloTag‐Based Reporters for Fluorescence Imaging and Biosensing

  2023cites this paper
• Optimized Red-Absorbing Dyes for Imaging and Sensing

  2023cites this paper
• N-Cyanorhodamines: cell-permeant, photostable and bathochromically shifted analogues of fluoresceins

  2022cites this paper
• A general, highly efficient and facile synthesis of biocompatible rhodamine dyes and probes for live-cell multicolor nanoscopy

  2022cites this paper
• Evaluating the Effect of Dye-Dye Interactions of Xanthene-Based Fluorophores in the Fluorosequencing of Peptides.

  2022cites this paper
• Bio‐Based Solar Energy Harvesting for Onsite Mobile Optical Temperature Sensing in Smart Cities

  2022cites this paper
• An investigation into the in vivo performance of Changsha and rhodamine fluorophores

  2022cites this paper
• Far-red to NIR emitting xanthene-based fluorophores

  2022cites this paper
• Xanthene dyes for cancer imaging and treatment: A material odyssey

  2022cites this paper
• Rhodamines with a Chloronicotinic Acid Fragment for Live Cell Superresolution STED Microscopy**

  2021cites this paper
• Silinanyl Rhodamines and Silinanyl Fluoresceins for Super-Resolution Microscopy.

  2021cites this paper
• A microtubule-localizing activity-based sensing fluorescent probe for imaging hydrogen peroxide in living cells.

  2021cites this paper
• Untangling the respective effects of heteroatom-doped carbon materials in batteries, supercapacitors and the ORR to design high performance materials

  2021cites this paper
• Blinking Fluorescent Probes for Tubulin Nanoscopy in Living and Fixed Cells

  2021cites this paper
• Six-Membered Rings with One Other Element

  2021cites this paper
• A general design of caging-group-free photoactivatable fluorophores for live-cell nanoscopy

  2021cites this paper
• Modular Synthetic Approach to Silicon-Rhodamine Homologues and Analogues via Bis-aryllanthanum Reagents

  2021cites this paper
• Photoactivatable Fluorescent Dyes with Hydrophilic Caging Groups and Their Use in Multicolor Nanoscopy

  2021cites this paper
• 2,2,2‐Trifluoroethyl(mesityl)iodonium Triflate

  2021cites this paper
• Silicon-substituted rhodamines for stimulated emission depletion fluorescence nanoscopy

  2021cites this paper
• Exploiting the potential of commercial digital holographic microscopy by combining it with 3D matrix cell culture assays

  2020cites this paper
• Between life and death: strategies to reduce phototoxicity in super-resolution microscopy

  2020cites this paper
• Enhancing the biocompatibility of rhodamine fluorescent probes by a neighbouring group effect† †Electronic supplementary information (ESI) available. See DOI: 10.1039/d0sc02154g

  2020cites this paper
• Efflux pump insensitive rhodamine-jasplakinolide conjugates for G- and F-actin imaging in living cells.

  2020cites this paper
• Synthesis of Fluorescent Jasplakinolide Analogues for Live-Cell STEDa Microscopy of Actin

  2020cites this paper
• Systematic study of synthesizing various heteroatom-substituted rhodamines from diaryl ether analogues.

  2020cites this paper
• Super modules-based active QR codes for smart trackability and IoT: a responsive-banknotes case study

  2020cites this paper
• What is best strategy for water soluble fluorescence dyes? - A case study using long fluorescence lifetime DAOTA dyes.

  2020cites this paper
• Multi-Factors Regulate the Spirocyclization Equilibrium of Si-Rhodamines.

  2020cites this paper
• Substitution of oxygen with silicon: A big step forward for fluorescent dyes in life science

  2020cites this paper
• Appreciating the small things in life: STED microscopy in living cells

  2020cites this paper
• Recent Progress in Small Spirocyclic, Xanthene-Based Fluorescent Probes

  2020cites this paper
• Enhancing biocompatibility of rhodamine fluorescent probes by a neighbouring group effect

  2020cites this paper
• Deep-Red Fluorescent Organic Nanoparticles with High Brightness and Photo-Stability for Super-Resolution In Vitro and In Vivo Imaging Using STED Nanoscopy.

  2019cites this paper
• Synthesis of Carboxy ATTO 647N Using Redox Cycling for Xanthone Access.

  2019cites this paper
• The checkpoint protein Zw10 connects CAL1-dependent CENP-A centromeric loading and mitosis duration in Drosophila cells

  2019cites this paper
• Between Life and Death: Reducing Phototoxicity in Super-Resolution Microscopy

  2019cites this paper
• Asymmetric and Reduced Xanthene Fluorophores: Synthesis, Photochemical Properties, and Application to Activatable Fluorescent Probes for Detection of Nitroreductase

  2019cites this paper
• ColiCoords: A Python package for the analysis of bacterial fluorescence microscopy data

  2019cites this paper
• Green‐Emitting Rhodamine Dyes for Vital Labeling of Cell Organelles Using STED Super‐Resolution Microscopy

  2019cites this paper
• Sustainable Liquid Luminescent Solar Concentrators

  2019cites this paper
• A simple empirical algorithm for optimising depletion power and resolution for dye and system specific STED imaging

  2019cites this paper
• Transparent Luminescent Solar Concentrators Using Ln3+-Based Ionosilicas Towards Photovoltaic Windows

  2019cites this paper
• Heteroatom-substituted rhodamine dyes: Structure and spectroscopic properties

  2019cites this paper
• Extended Triangulenium Ions: Syntheses and Characterization of Benzo-Bridged Dioxa- and Diazatriangulenium Dyes.

  2019cites this paper
• Fluorogenic probes for super-resolution microscopy.

  2019cites this paper
• Novel fluorescent probes and analysis methods for single-molecule and single-cell microscopy

  2019cites this paper
• Far-red/near-infrared emitting, two-photon absorbing, and bio-stable amino-Si-pyronin dyes

  2019cites this paper
• Centromeric CENP-A loading requires accurate mitotic timing, which is linked to checkpoint proteins

  2018cites this paper
• Rhodamine–Hoechst positional isomers for highly efficient staining of heterochromatin

  2018cites this paper
• Triarylmethane Fluorophores Resistant to Oxidative Photobluing

  2018cites this paper
• Small-Molecule Fluorescent Probes for Live-Cell Super-Resolution Microscopy.

  2018cites this paper
• Fluorescent dyes and probes for super-resolution microscopy of microtubules and tracheoles in living cells and tissues

  2018cites this paper
• Live-cell labeling of endogenous proteins with nanometer precision by transduced nanobodies

  2018cites this paper
• Calibration-free In Vitro Quantification of Protein Homo-oligomerization Using Commercial Instrumentation and Free, Open Source Brightness Analysis Software.

  2018cites this paper
• Robust nanoscopy of a synaptic protein in living mice by organic-fluorophore labeling

  2018cites this paper
• Photoactivatable Rhodamine Spiroamides and Diazoketones Decorated with "Universal Hydrophilizer" or Hydroxyl Groups.

  2018cites this paper
• Sustainable luminescent solar concentrators based on organic-inorganic hybrids modified with chlorophyll

  2018cites this paper
• Separation of the 5- and 6-Carboxy Regioisomers of ROX and JOE Dyes with Examples of N-(3-Azidopropyl)amide Synthesis

  2018cites this paper
• Hydroxylated Fluorescent Dyes for Live‐Cell Labeling: Synthesis, Spectra and Super‐Resolution STED†

  2017cites this paper
• General Synthetic Method for Si-Fluoresceins and Si-Rhodamines

  2017cites this paper
• Silicon-substituted Xanthene Dyes and Their Unique Photophysical Properties for Fluorescent Probes.

  2017cites this paper
• Two-Color 810 nm STED Nanoscopy of Living Cells with Endogenous SNAP-Tagged Fusion Proteins.

  2017cites this paper
• Long-Term Live-Cell STED Nanoscopy of Primary and Cultured Cells with the Plasma Membrane HIDE Probe DiI-SiR.

  2017cites this paper
• Cell-Permeant Large Stokes Shift Dyes for Transfection-Free Multicolor Nanoscopy.

  2017cites this paper
• HIDE Probes: A New Toolkit for Visualizing Organelle Dynamics, Longer and at Super-Resolution.

  2017cites this paper
• High-Affinity Functional Fluorescent Ligands for Human β-Adrenoceptors

  2017cites this paper
• Evaluating the E ff ect of Dye − Dye Interactions of Xanthene-Based Fluorophores in the Fluorosequencing of Peptides

  year unknowncites this paper