Turn-on Fluorene Push–Pull Probes with High Brightness and Photostability for Visualizing Lipid Order in Biomembranes

Shaya, Janah; Collot, Mayeul; Bénailly, Frédéric; Mahmoud, Najiba; Mély, Yves; Michel, Benoît Y.; Klymchenko, Andrey S.; Burger, Alain

doi:10.1021/acschembio.7b00658

Cited by 45 publications

(45 citation statements)

References 59 publications

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“…Some of these were applied successfully to study lipid droplets 14,17,25,[37][38][39][40] and biomembranes. 14,25,41,42 In particular, we should mention a push-pull pyrene (PA, Figure 1), which, in comparison with Laurdan, shows much brighter fluorescence and better photostability, and absorbs in the convenient violet region, while preserving its sensitivity to lipid order in membranes. 14,34 Owing to its cell permeability and strong solvatochromism, it enabled mapping polarity in live cells, revealing an increase in polarity from cell plasma membranes towards intracellular membranes.…”

Section: Introductionmentioning

confidence: 99%

Polarity Mapping of Cells and Embryos by Improved Fluorescent Solvatochromic Pyrene Probe

et al. 2020

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Solvatochromic dyes enable sensing and imaging of biomolecular organization in living systems by monitoring local polarity (lipophilicity), but most such dyes suffer from limited brightness, photostability, lack of a convenient spectral range and limited sensitivity to polarity. Moreover, the presence of an electron acceptor group, typically a carbonyl, in their push-pull structure raises concerns about their potential chemical reactivity within the biological environment. In order to achieve robust bioimaging, we synthesized a push-pull pyrene probe bearing a ketone acceptor group (PK) and compared it with a recently developed aldehyde analogue (PA). We found that in live cells the aldehyde analogue PA transforms slowly (in ~100 min) into blue-emissive species, assigned to in situ formation of an imine analogue, whereas the PK probe is stable in the presence of primary amines and inside cells. Like the parent PA, the new probe shows strong solvatochromism and an emission color response to lipid order in membranes (ordered vs. disordered liquid phases), while its blue-shifted absorption is more optimal for excitation with 400-nm light sources. In live cells, the PK probe enables high-contrast polarity mapping of organelles using two-color ratiometric detection, suggesting that polarity increases in the following order: lipid droplets < plasma membranes < endoplasmic reticulum. In the zebrafish embryo, polarity imaging with the PK probe reveals a new dimension in visualizing the organization of tissueslipophilicity distribution, where biomembranes, lipid droplets, cells, yolk, extracellular space and newly formed organs are revealed by specific emission wavelengths of the probe. The newly developed probe and the proposed approach of polarity mapping open new opportunities for bioimaging at the cellular and animal level.

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Section: Introductionmentioning

confidence: 99%

Polarity Mapping of Cells and Embryos by Improved Fluorescent Solvatochromic Pyrene Probe

et al. 2020

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“…From these two observations, numerous efforts have been made to develop fluorescent PM probes 4,5,6,7 including from our group. [8][9][10][11][12][13][14][15] Among them, FM dyes (named after Fei Mao 16 ), which are styryl dyes introduced by Betz and colleagues in the early 90s' as synaptic vesicle markers, 16 rapidly became among the most famous and used commercially available PM probes. 17,18 These amphiphilic dyes were further developed by the group of Loew to give rise to PM voltage sensitive probes 19,20 and membrane lipid domains probes.…”

Section: Introductionmentioning

confidence: 99%

Molecular Tuning of Styryl Dyes Leads to Versatile and Efficient Plasma Membrane Probes for Cell and Tissue Imaging

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Fam

et al. 2019

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The plasma membrane (PM) plays a major role in many biological processes; therefore its proper fluorescence staining is required in bioimaging. Among the commercially available PM probes, styryl dye FM1-43 is one of the most widely used. In this work, we demonstrated that fine chemical modifications of FM1-43 can dramatically improve the PM staining. The newly developed probes, SP-468 and SQ-535 were found to display enhanced photophysical properties (reduced crosstalk, higher brightness, improved photostability) and unlike FM1-43, provided excellent and immediate PM staining in 5 different mammalian cell lines including neurons (primary culture and tissue imaging). Additionally, we showed that the new probes displayed differences in their internalization pathways compared to their parent FM1-43. Finally, we demonstrated that the modifications made to FM1-43 did not impair the ability of the new probes to stain the PM of plant cells. Overall, this work presents new useful probes for PM imaging in cells and tissues and provides insights on the molecular design of new PM targeting molecules.

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“…Solvatochromic dyes display different emission wavelengths depending on their environment's polarity. 42 By means of chemical modifications certain of these fluorophores like Nile Red, 43 pyrene, 44 and fluorene 45 were successfully used to selectively probe polarity of the plasma membrane and/or intracellular membranes respectively, using ratiometric imaging. Herein we developed a push-pull fluorophore, Dimethyl Aniline Furaldehyde (DAF) that displayed positive solvatochromic properties in emission.…”

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Probing Polarity and Heterogeneity of Lipid Droplets in Live Cells Using a Push–Pull Fluorophore

et al. 2018

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Lipid droplets (LDs) are organelles composed of a lipid core surrounded by a phospholipid monolayer. Lately, LDs attracted a considerable attention due to recent studies demonstrating their role in a variety of physiological processes as well as diseases. Herein we synthesized a push-pull molecule named DAF (Dimethyl Aniline Furaldehyde) that possesses a strong positive solvatochromism in emission of 119 nm from toluene to methanol. Its impressive fluorogenic properties from water to oil (2000fold) as well as its high quantum yields (up to 0.97) led us to investigate its ability to sense the distribution of polarity in live cells by fluorescence ratiometric imaging. When added to live cells and excited at 405 nm, DAF immediately and brightly stain lipid droplets using a blue channel (410-500 nm) and cytoplasm in a red channel (500-600 nm). DAF also proved to be compatible with fixation thus allowing 3D imaging of LDs in their cytoplasm environment. Taking advantage of DAF emission in two distinct channels, ratiometric imaging was successfully performed and led to the polarity mapping of the cell unraveling some heterogeneity in polarity within LDs of the same cell.

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Turn-on Fluorene Push–Pull Probes with High Brightness and Photostability for Visualizing Lipid Order in Biomembranes

Cited by 45 publications

References 59 publications

Polarity Mapping of Cells and Embryos by Improved Fluorescent Solvatochromic Pyrene Probe

Polarity Mapping of Cells and Embryos by Improved Fluorescent Solvatochromic Pyrene Probe

Molecular Tuning of Styryl Dyes Leads to Versatile and Efficient Plasma Membrane Probes for Cell and Tissue Imaging

Probing Polarity and Heterogeneity of Lipid Droplets in Live Cells Using a Push–Pull Fluorophore

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