Development and characterization of BODIPY-derived tracers for fluorescent labeling of the endoplasmic reticulum

Jong, Flip de; Pokorný, Jan; Manshian, Bella B.; Daelemans, Brent; Vandaele, Johannes; Startek, Justyna B.; Soenen, Stefaan; Auweraer, Mark Van der; Dehaen, Wim; Rocha, Susana; Silveira-Dorta, Gastón

doi:10.1016/j.dyepig.2020.108200

Cited by 8 publications

(8 citation statements)

References 49 publications

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“…Furthermore, we also noticed that the cytoplasmic vacuolization observed in Dfcy-treated cells arises from the ER but not the mitochondria (Figure 3a). We then visualized ER in living cells by staining with an ER-tracker (a fluorescent dye that binds to the sulfonylurea receptor-the regulatory subunit of the ATP-sensitive K + channel prominently expressed in the ER) (de Jong et al, 2020), to confirm that cytoplasmic vacuoles arise from dilated ER. Confocal imaging shows that the ER-tracker localized to membranes of the distinctive vacuoles formed in Dfcy-treated cells, indicating that Dfcy treatment induced ER dilation (Figure 3b).…”

Section: Resultsmentioning

confidence: 99%

The iron chelator deferriferrichrysin induces paraptosis via extracellular signal‐related kinase activation in cancer cells

et al. 2023

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Cancer cells generally exhibit increased iron uptake, which contributes to their abnormal growth and metastatic ability. Iron chelators have thus recently attracted attention as potential anticancer agents. Here, we show that deferriferrichrysin (Dfcy), a natural product from Aspergillus oryzae acts as an iron chelator to induce paraptosis (a programmed cell death pathway characterized by ER dilation) in MCF‐7 human breast cancer cells and H1299 human lung cancer cells. We first examined the anticancer efficacy of Dfcy in cancer cells and found that Dfcy induced ER dilation and reduced the number of viable cells. Extracellular signal‐related kinase (ERK) was activated by Dfcy treatment, and the MEK inhibitor U0126, a small molecule commonly used to inhibit ERK activity, prevented the increase in ER dilation in Dfcy‐treated cells. Concomitantly, the decrease in the number of viable cells upon treatment with Dfcy was attenuated by U0126. Taken together, these results demonstrate that the iron chelator Dfcy exhibits anticancer effects via induction of ERK‐dependent paraptosis.

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Section: Resultsmentioning

confidence: 99%

The iron chelator deferriferrichrysin induces paraptosis via extracellular signal‐related kinase activation in cancer cells

et al. 2023

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“…Although an essential cellular organelle there are relatively few BDP dyes specifically designed to target the ER [12–17] . Their emissive properties and low cytotoxicity make them ideal as fluorescent probes for biological systems; however, post‐functionalization is often required to ensure specific localization.…”

Section: Introductionmentioning

confidence: 99%

“…Of course, the intensity of the imaging is dependent on the amount of these receptors expressed and binding to these receptors may lead to interference of normal ER function. A recent report studied a series of 19 BODIPY small fluorescent molecules (SFMs) as probes for the ER [14] . These probes were synthesized from 2,4‐dimethyl pyrrole reactions with 2‐quinolinecarboxalehydes differing by organic substituents at the 8‐position.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Endoplasmic Reticulum Targeting Isoquinol‐Based BODIPY Dyes and Their Properties as Molecular Rotors

Swavey,

Heidary,

Boyd

et al. 2023

Eur J Org Chem

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A series of six new isoquinol‐based BODIPY dyes have been synthesized by a two‐step method. Unlike traditional synthetic methods, synthesis did not require the use of oxidizing agents or solvent. Spectroscopic, electrochemical and DFT calculations indicate that the properties associated with the six dyes are very similar with little influence of the meso‐substituents. Viscosity studies identified three of the new dyes having properties of molecular rotors for applications in the detection of changes in cellular viscosity. Incubation of the dyes with the HEK cell line show no toxicity up to 10 μM over a 72 h. period. The dyes show the ability to localize within the endoplasmic reticulum (ER) of cells. With two of the dyes showing favorable comparisons to commercially available ER dyes.

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“…3,4 Furthermore, owing to its strong electron-withdrawing effect, the difluoroboron group can facilitate intramolecular charge transfer (ICT), leading to small bandgaps and long absorption and emission wavelengths. 4–8 The benefits of incorporating this difluoroboron moiety have fueled the development of a multitude of organoboron compounds, including BODIPY, 2,9,10 BOPAHY, 11–13 BOPHY 14,15 and BOPPY 16 derivatives (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…Applications such as light harvesting, optoelectronic devices, chemical sensing, biological imaging and medical theranostics have been reported for these dyes. 2,8,10–16…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical properties of (post-)functionalized BOAHY dyes with strong aggregation-induced emission

Vandenwijngaerden,

Huang,

Cresens

et al. 2023

Mater. Adv.

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Development and characterization of BODIPY-derived tracers for fluorescent labeling of the endoplasmic reticulum

Cited by 8 publications

References 49 publications

The iron chelator deferriferrichrysin induces paraptosis via extracellular signal‐related kinase activation in cancer cells

The iron chelator deferriferrichrysin induces paraptosis via extracellular signal‐related kinase activation in cancer cells

Evaluation of Endoplasmic Reticulum Targeting Isoquinol‐Based BODIPY Dyes and Their Properties as Molecular Rotors

Synthesis and photophysical properties of (post-)functionalized BOAHY dyes with strong aggregation-induced emission

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