BODIPYs with Photoactivatable Fluorescence

Zhang, Yang; Zheng, Yeting; Meana, Yasniel; Raymo, Françisco M.

doi:10.1002/chem.202101628

Cited by 30 publications

(27 citation statements)

References 108 publications

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“…In turn, the inability to visualize the sample complicates the identification of regions within the field of view that would be appropriate for activation. In spite of these complications, photocaged acridinones, azafluorenones, benzothiazoles, borondipyrromethenes (BODIPYs), coumarins, cyanines, diazaxanthilidenes, fluoresceins, pyrazolines, resorufin, rhodamines, salens, tetraethylenes, and xanthene have already been employed successfully to monitor diverse dynamic events in developing embryos and live cells on the basis of FPD. − …”

Section: Fluorescence Photoactivation To Monitor Dynamicsmentioning

confidence: 99%

Photoactivatable Fluorophores for Bioimaging Applications

Zhang

Zheng

Tomassini

et al. 2023

ACS Appl. Opt. Mater.

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Photoactivatable fluorophores provide the opportunity to switch fluorescence on exclusively in a selected area within a sample of interest at a precise interval of time. Such a level of spatiotemporal fluorescence control enables the implementation of imaging schemes to monitor dynamic events in real time and visualize structural features with nanometer resolution. These transformative imaging methods are contributing fundamental insights on diverse cellular processes with profound implications in biology and medicine. Current photoactivatable fluorophores, however, become emissive only after the activation event, preventing the acquisition of fluorescence images and, hence, the visualization of the sample prior to activation. We developed a family of photoactivatable fluorophores capable of interconverting between emissive states with spectrally resolved fluorescence, instead of switching from a nonemissive state to an emissive one. We demonstrated that our compounds allow the real-time monitoring of molecules diffusing across the cellular blastoderm of developing embryos as well as of polymer beads translocating along the intestinal tract of live nematodes. Additionally, they also permit the tracking of single molecules in the lysosomal compartments of live cells and the visualization of these organelles with nanometer resolution. Indeed, our photoactivatable fluorophores may evolve into invaluable analytical tools for the investigation of the fundamental factors regulating the functions and structures of cells at the molecular level.

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Section: Fluorescence Photoactivation To Monitor Dynamicsmentioning

confidence: 99%

Photoactivatable Fluorophores for Bioimaging Applications

Zhang

Zheng

Tomassini

et al. 2023

ACS Appl. Opt. Mater.

Self Cite

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“…They have also been used as fluorescent agents to label a variety of different ligands, including proteins [ 20 , 21 ], DNA [ 22 , 23 ], carbohydrates and lipids [ 24 , 25 ], peptides [ 26 , 27 ], and steroid hormones [ 28 , 29 , 30 ]. These properties have led researchers to explore their biomedical applications as photosensitizers in photodynamic therapy (PDT) [ 31 , 32 , 33 ], positron emission tomography (PET) [ 34 , 35 , 36 ], and fluorescence imaging [ 37 , 38 ].…”

Section: Introductionmentioning

confidence: 99%

Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms: Cancer Theranostic Dyes

Amendoeira

Luz

Valente

et al. 2023

IJMS

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Estradiol-BODIPY linked via an 8-carbon spacer chain and 19-nortestosterone- and testosterone-BODIPY linked via an ethynyl spacer group were evaluated for cell uptake in the breast cancer cell lines MCF-7 and MDA-MB-231 and prostate cancer cell lines PC-3 and LNCaP, as well as in normal dermal fibroblasts, using fluorescence microscopy. The highest level of internalization was observed with 11β-OMe-estradiol-BODIPY 2 and 7α-Me-19-nortestosterone-BODIPY 4 towards cells expressing their specific receptors. Blocking experiments showed changes in non-specific cell uptake in the cancer and normal cells, which likely reflect differences in the lipophilicity of the conjugates. The internalization of the conjugates was shown to be an energy-dependent process that is likely mediated by clathrin- and caveolae-endocytosis. Studies using 2D co-cultures of cancer cells and normal fibroblasts showed that the conjugates are more selective towards cancer cells. Cell viability assays showed that the conjugates are non-toxic for cancer and/or normal cells. Visible light irradiation of cells incubated with estradiol-BODIPYs 1 and 2 and 7α-Me-19-nortestosterone-BODIPY 4 induced cell death, suggesting their potential for use as PDT agents.

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“…These two lights have to be synchronized spatially and temporally. [13] In addition, UV would damage the bio-samples. Efforts have been made to achieve photoactivation under visible light illumination.…”

Section: Introductionmentioning

confidence: 99%

A Universal Photoactivatable Tag Attached to Fluorophores Enables Their Use for Single‐Molecule Imaging

et al. 2022

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Single molecule localization microscopy based on photoactivation is a powerful tool for investigating the ultrastructure of cells. We developed a general strategy for photoactivatable fluorophores, using 2,3dihydro-1,4-oxathiine group (SO) as a tag to attach to various skeletal structures, including coumarin, BODI-PY, rhodamine, and cyanine. The conjugation of SO resulted in a significant loss of fluorescence due to photoinduced electron transfer (PeT). Under the irradiation of excitation light, singlet oxygen generated by the fluorophores converted the SO moiety into its ester derivative, terminated the PeT process, and restored the fluorescence. Single molecule localization imaging was achieved using a dual functional illuminating beam in the visible, acting as both the activating and the exciting source. We successfully applied these photoactivatable probes for time-lapse super-resolution tracking in living cells and super-resolution imaging of microtubule structures in neurons.

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BODIPYs with Photoactivatable Fluorescence

Abstract: Dedicated to Vincenzo Balzani on the occasion of his 85th birthday.

Cited by 30 publications

References 108 publications

Photoactivatable Fluorophores for Bioimaging Applications

Photoactivatable Fluorophores for Bioimaging Applications

Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms: Cancer Theranostic Dyes

A Universal Photoactivatable Tag Attached to Fluorophores Enables Their Use for Single‐Molecule Imaging

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