Advances in the design of cell-permeable fluorescent probes for applications in live cell imaging

Alamudi, Samira Husen; Chang, Young‐Tae

doi:10.1039/c8cc08107g

Cited by 57 publications

(25 citation statements)

References 70 publications

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“…6,154.7,154.6,152.5,151.8,127.1,120.7 (q,J = 323 Hz,Tf),118.7,116.8,111.6,110.4,109.2,96.0,73.4,46.5,44.2,18.5,12.3. 19 F NMR (376 MHz, 3,163.4,155.6,155.5,152.7,152.2,147.5,127.5,120.7 (q,J = 323 Hz,Tf),117.4,114.8,113.1,111.5,110.7,95.9,44.4,42.5,18.9,12.4. 19 F NMR (376 MHz, 2,158.8,156.0,155.4,154.5,153.1,152.4,136.7 (q,J = 32 Hz),125.4,124.9,121.5 (q,J = 277 Hz),120.5 (q,J = 323 Hz),116.6,…”

Section: -(Pyrimidin-4-yl)acetonitrile (16)mentioning

confidence: 99%

Modulating Photostability and Mitochondria Selectivity in Far-Red/NIR Emitting Coumarin Fluorophores through Replacement of Pyridinium by Pyrimidinium

et al. 2020

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Mitochondrial dysfunction has been associated with several human pathologies, including cancer, aging and neurodegenerative diseases. Thus, the availability of selective fluorescent probes for mitochondria could play an important role in the future for monitoring cellular function and disease progression. In this work, we have studied how the photophysical properties and subcellular accumulation of nonconventional coumarin-based COUPY fluorophores can be fine-tuned through replacement of the para-pyridinium moiety with several heterocycles. Among them, ortho,para-pyrimidinium substitution provided novel fluorophores with suitable photophysical properties for bioimaging applications, including emission in the far-red to NIR region, large Stokes' shifts and high photostability.Furthermore, the compounds exhibited excellent cell membrane permeability in living cells and a higher selectivity for mitochondria compared with the parent COUPY fluorophores.Overall, these results provide useful insights for the development of novel mitochondriatargeted fluorescent probes based on small organic molecules, since higher selectivity for this organelle can be achieved through the replacement of conventional N-alkylated pyridinium moieties by the corresponding N-alkylated-ortho,para-pyrimidinium counterparts.

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Section: -(Pyrimidin-4-yl)acetonitrile (16)mentioning

confidence: 99%

Modulating Photostability and Mitochondria Selectivity in Far-Red/NIR Emitting Coumarin Fluorophores through Replacement of Pyridinium by Pyrimidinium

et al. 2020

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“…Once we had intermediate NBDP-yne in hand, we proceeded to its chemical derivatization. As a proof of concept, we chose to introduce ammonium and phosphonium moieties as groups that had been described before for the labelling of mitochondria [21][22][23][24]. These groups where easily introduced by standard click-chemistry (CuSO4, sodium ascorbate) in NBDP-yne, using the corresponding azide-functionalized reagent (see Scheme 2).…”

Section: Derivatization Of Key Intermediate Nbdp-yne Towards Bio-recomentioning

confidence: 99%

Alkynyl N-BODIPYs as Reactive Intermediates for the Development of Dyes for Biophotonics

Ray

García-Sampedro

Schad

et al. 2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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A new approach for the rapid multi-functionalization of BODIPY dyes towards biophotonics is reported. It is based on novel N-BODIPYs, through reactive intermediates with alkynyl groups to be further derivatized by click chemistry. This approach has been exemplified by the development of new dyes for cell bio-imaging, which have proven to successfully internalize into pancreatic cancer cells and accumulate in the mitochondria. The in vitro suitability for photodynamic therapy (PDT) was also analyzed and confirmed our compounds to be promising PDT candidates for the treatment of pancreatic cancer.

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“…Our findings gain relevance as it is well known that the development of fluorophores that selectively reveal subcellular compartments depending from the laser source, as the curcumin derivatives described here, may provide crucial information of organelle’s function [ 38 , 40 ]. An additional feature of the fluorophores reported here is the permeation of the human cell membrane preserving its integrity, which is essential to understand intracellular functions [ 41 ]. Furthermore, the high permeability of 2 and 5 can be attributed to their excellent lipophilicity, as demonstrated by their partition coefficients with log P values of 2.16 ± 0.069 and 1.82 ± 0.222, respectively.…”

Section: Resultsmentioning

confidence: 99%

Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging

et al. 2020

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Curcumin, the most important secondary metabolite isolated from Curcuma longa, is known for its numerous purported therapeutic properties and as a natural dye. Herein, based on curcumin’s intrinsic fluorescence, a search for improved curcumin-based fluorophores was conducted. Within the set of semi-synthetic curcumin derivatives i.e. mono (1), di (2), tri (3), tetra (4) benzylated and dibenzyl-fluoroborate (5), the fluorescence properties of 2 and 5 in solution outstood with a two-fold quantum yield compared to curcumin. Furthermore, all benzylated derivatives showed a favorable minimal cytotoxic activity upon screening at 25 μM against human cancer and non-tumoral COS-7 cell lines, with a reduction of its cytotoxic effect related to the degree of substitution. Fluorophores 2 and 5 are versatile bioimaging tools, as revealed by Confocal Fluorescence Microscopy (CFM), and showed permeation of living cell membranes of astrocytes and astrocytomas. When 2 is excited with a 405- (blue) or 543-nm (green) laser, it is possible to exclusively and intensively visualize the nucleus. However, the fluorescence emission fades as the laser wavelength moves towards the red region. In comparison, 5 allows selective visualization of cytoplasm when a 560-nm laser is used, showing emission in the NIR region, while it is possible to exclusively observe the nucleus at the blue region with a 405-nm laser.

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Advances in the design of cell-permeable fluorescent probes for applications in live cell imaging

Abstract: Advances in the design strategy of cell-permeable small fluorescent probes are discussed. Their applications in imaging specific cell types and intracellular bioanalytes, as well as the cellular environment in live conditions, are presented.

Cited by 57 publications

References 70 publications

Modulating Photostability and Mitochondria Selectivity in Far-Red/NIR Emitting Coumarin Fluorophores through Replacement of Pyridinium by Pyrimidinium

Modulating Photostability and Mitochondria Selectivity in Far-Red/NIR Emitting Coumarin Fluorophores through Replacement of Pyridinium by Pyrimidinium

Alkynyl N-BODIPYs as Reactive Intermediates for the Development of Dyes for Biophotonics

Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging

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