Fluorescence and confocal imaging of mammalian cells using conjugated oligoelectrolytes with phenylenevinylene core

Milczarek, Justyna; Pawłowska, Róża; Żurawiński, Remigiusz; Łukasik, Beata; Garner, Logan E.; Chworoś, Arkadiusz

doi:10.1016/j.jphotobiol.2017.03.017

Cited by 12 publications

(11 citation statements)

References 49 publications

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“…Summarizing, all tested SN-COEs show a blue-shift from aqueous PBS buffer to suspended K562 cells and to HeLa, suggesting an increase in hydrophobicity. This phenomenon was previously observed for SN-COEs diluted in organic solvents [36] and for previously tested phenylene-vinylene derivatives (PV-COEs) [23,27]. Moreover, the higher fluorescence intensity of the tested compounds after incorporation into lipid membranes is depending on their structure.…”

Section: Evaluation Of Spectral Properties Of the Dsnn-derivativessupporting

confidence: 66%

“…Phenylenevinylene COEs were successfully incorporated into bacteria [15,25] and yeast cells [12,23]. Owing to their affinity for membranes and fluorophoric nature, they can quickly diffuse into mammalian cells and stain cellular membranous components, like endoplasmic reticulum and Golgi apparatuses without significant cytotoxicity [26,27]. Moreover, some date indicates that, not only intercellular membranous organelles, but also extracellular structures may be visualized using this class of compounds.…”

Section: Introductionmentioning

confidence: 99%

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Highly Fluorescent Distyrylnaphthalene Derivatives as a Tool for Visualization of Cellular Membranes

et al. 2020

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Fluorescent imaging, which is an important interdisciplinary field bridging research from organic chemistry, biochemistry and cell biology has been applied for multi-dimensional detection, visualization and characterization of biological structures and processes. Especially valuable is the possibility to monitor cellular processes in real time using fluorescent probes. In this work, conjugated oligoelectrolytes and neutral derivatives with the distyrylnaphthalene core (SN-COEs) were designed, synthetized and tested for biological properties as membrane-specific fluorescent dyes for the visualization of membrane-dependent cellular processes. The group of tested compounds includes newly synthesized distyrylnaphthalene derivatives (DSNNs): a trimethylammonium derivative (DSNN-NMe3+), a phosphonate derivative (DSNN-P), a morpholine derivative (DSNN-Mor), a dihydroxyethylamine derivative (DSNN-DEA), a phosphonate potassium salt (DSNN-POK), an amino derivative (DSNN-NH2) and pyridinium derivative (DSNN-Py+). All compounds were tested for their biological properties, including cytotoxicity and staining efficiency towards mammalian cells. The fluorescence intensity of SN-COEs incorporated into cellular structures was analyzed by fluorescence activated cell sorting (FACS) and photoluminescence spectroscopy. The cytotoxicity results have shown that all tested SN-COEs can be safely used in the human and animal cell studies. Fluorescence and confocal microscopy observations confirm that tested COEs can be applied as fluorescent probes for the visualization of intracellular membrane components in a wide range of different cell types, including adherent and suspension cells. The staining procedure may be performed under both serum free and complete medium conditions. The presented studies have revealed the interesting biological properties of SN-COEs and confirmed their applicability as dyes for staining the membranous structures of eukaryotic cells, which may be useful for visualization of wide range of biological processes dependent of the extra-/intracellular communications and/or based on the remodeling of cellular membranes.

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Section: Evaluation Of Spectral Properties Of the Dsnn-derivativessupporting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Highly Fluorescent Distyrylnaphthalene Derivatives as a Tool for Visualization of Cellular Membranes

et al. 2020

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“…MICOEs may also prove useful for labeling cellular organelles and subcompartments [108][109][110] . To ascertain the suitability of MICOEs as staining agents for fluorescence-based bioimaging of live and fixed mammalian cells, Chworos and co-workers studied DSSN+ and another two derivatives, DSBN+ and COE1-5C, on three mammalian cell types.…”

Section: Linear Membrane-intercalating Coes For Membrane System Imagingmentioning

confidence: 99%

Precisely Defined Conjugated Oligoelectrolytes for Biosensing and Therapeutics

et al. 2019

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Conjugated oligoelectrolytes (COEs) are a relatively new class of synthetic organic molecules with, as of yet, untapped potential for use in organic optoelectronic devices and bioelectronics systems. COEs also offer a novel molecular approach to biosensing, bioimaging, and disease therapy. Substantial progress has been made in the past decade at the intersection of chemistry, materials science and the biological sciences developing COEs and their polymer analogues, namely conjugated polyelectrolytes (CPEs), into synthetic systems with biological and biomedical utility. CPEs have traditionally attracted more attention in arenas of sensing, imaging, and therapy. However, the precisely-defined molecular structures and interactions of COEs offer potential key advantages over CPEs, including higher reliability and fluorescence quantum efficiency, larger diversity of subcellular targeting strategies, and improved selectivity to biomolecules. Here, the unique -and sometimes overlooked -properties of COEs are discussed and the noticeable progress in their use for biological sensing, imaging and therapy is reviewed.Received: ((will be filled in by the editorial staff))Revised: ((will be filled in by the editorial staff))

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“…The cytotoxicity of all compounds was determined by the MTT [3-(4,5dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide; Sigma, St. Louis, MO] assay as described previously. 61 Each viability point represents the mean AE SE from at least three independent experiments performed thrice. The IC 50 values were calculated from the dose-response curves.…”

Section: Cell Viability Testmentioning

confidence: 99%

A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A

et al. 2020

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Fluorescence and confocal imaging of mammalian cells using conjugated oligoelectrolytes with phenylenevinylene core

Cited by 12 publications

References 49 publications

Highly Fluorescent Distyrylnaphthalene Derivatives as a Tool for Visualization of Cellular Membranes

Highly Fluorescent Distyrylnaphthalene Derivatives as a Tool for Visualization of Cellular Membranes

Precisely Defined Conjugated Oligoelectrolytes for Biosensing and Therapeutics

A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A

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