BODIPY-Ethynylestradiol molecular rotors as fluorescent viscosity probes in endoplasmic reticulum

Martínez-Bourget, Diego; Rocha, Érika da Justa Teixeira; Labra‐Vázquez, Pablo; Santillán, Rosa; Ortiz-López, Benjamín; Ortı́z-Navarrete, Vianney; Maraval, Valérie; Chauvin, Rémi; Farfán, Norberto

doi:10.1016/j.saa.2022.121704

Cited by 10 publications

(13 citation statements)

References 77 publications

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“…The evaluated optical energy was about 2.23 eV. The theoretical optical transition obtained by the TD-DFT calculation is in accordance with that determined experimentally [ 78 ]. Recognizable functionality groups of palladium phthalocyanine can be deduced depending on the position of the peak and the intensity of the infrared spectrum.…”

Section: Resultssupporting

confidence: 84%

Experimental and Theoretical Studies on Optical Properties of Tetra(Imidazole) of Palladium (II) Phthalocyanine

et al. 2022

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In this work, the optical properties of tetra(imidazole) of palladium phthalocyanine (PdPc(Im)4) in solution form and thin films on glass and fluorine-doped tin oxide (FTO) substrates were investigated via the thermal evaporation technique. The optical band gap was evaluated by ultraviolet–visible spectroscopy (UV-Vis). The energy band gap values were determined based on the Tauc graph. In addition, time-dependent density functional theory (TD-DFT) was used to simulate the UV-Vis absorption spectrum of the (PdPc(Im)4) molecule in the Dimethyl Sulfoxide (DMSO) solution phase. A good correlation was found between the DFT results and the experimental optical results. The band gap values between the experimental and DFT-simulated values are presented. The energy band gap of (PdPc(Im)4) obtained from the DFT calculations showed that it can be efficiently regulated. Frontier molecular orbitals and molecular electrostatic potentials were also proposed in this work. The surface study of the layers deposited on FTO was considered by atomic force microscopy (AFM) and scanning electron microscopy (SEM), and the results demonstrated good homogeneity covering the entire surface. The SEM image showed a homogeneous distribution of the grains with some spherical or rod-shaped structures and no agglomeration structures. This work rendered a strategy for regulating the energy band gap and compared the experimental observations obtained with theoretical studies, which provides a fundamental insight into the optical band for optoelectronic and thin-film solar cells.

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Section: Resultssupporting

confidence: 84%

Experimental and Theoretical Studies on Optical Properties of Tetra(Imidazole) of Palladium (II) Phthalocyanine

et al. 2022

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“…The BDP dyes 1 – 6 , Scheme 1, were synthesized by reacting isoquinopyrrole [17] and a variety of commercially available substituted phenyl aldehydes by first combining the reactants in a round bottom flask in the presence of enough solvent to dissolve the reagents and a few drops of trifluoroacetic acid (TFA). The solvent was removed under reduced pressure and the solid reactants were heated until a noticeable color change (red/purple) was observed.…”

Section: Resultsmentioning

confidence: 99%

“…All chemicals were reagent grade and used without further purification. Isoquino[5,6‐c]pyrrole was synthesized as previously described [17] . Chromatography was performed on a Teledyne CombiflashRf+ equipped with UV detection.…”

Section: Methodsmentioning

confidence: 99%

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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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“…To confirm this fact, we measured the fluorescence QY in a series of solvents having different polarity (Table 2). A library of meso-substituted BODIPYs was studied in [39], and it was showed that their fluorescence, if quenched in polar solvents due to PET, turns on in non-polar solvents. Our results confirms that the probability of PET is is indeed low.…”

Section: Photoinduced Release Of Nomentioning

confidence: 99%

A Novel Scaffold for Nitric Oxide Photo-Releasers based on Meso-Aminomethyl-BODIPY

Panfilov

Karogodina

Sibiryakova³

et al. 2022

Preprint

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Nitric oxide (NO) is a unique biochemical mediator involved in the regulation of vital processes. Its short half-life and local action impede direct application in medicine because highly targeted NO-delivery systems are required. Light-controllable NO releasers are promising for the development of smart therapies. Here we present novel simply prepared meso-aminomethyl BODIPY dyes containing N-Nitroso moiety and show the photoinduced generation of NO in a solution. As an example of NO-mediated effects, we demonstrate efficient light-dependent inhibition of platelet activation in vitro. We also show that some compounds could additionally generate singlet oxygen, which is promising for the photodynamic therapy. The presented compounds could serve as the basis for the development of novel hybrid therapeutic methods.

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BODIPY-Ethynylestradiol molecular rotors as fluorescent viscosity probes in endoplasmic reticulum

Cited by 10 publications

References 77 publications

Experimental and Theoretical Studies on Optical Properties of Tetra(Imidazole) of Palladium (II) Phthalocyanine

Experimental and Theoretical Studies on Optical Properties of Tetra(Imidazole) of Palladium (II) Phthalocyanine

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

A Novel Scaffold for Nitric Oxide Photo-Releasers based on Meso-Aminomethyl-BODIPY

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