Modulation of the photophysical properties of multi-BODIPY-siloxane conjugates by varying the number of fluorophores

Пахомов, А. А.; Kim, Eleonora E.; Kononevich, Yuriy N.; Ionov, D. S.; Maksimova, M. А.; Khalchenia, Veronika B.; Maksimov, Eugene G.; Анисимов, А. А.; Shchegolikhina, Olga I.; Martynov, Vladimir I.; Музафаров, А. М.

doi:10.1016/j.dyepig.2022.110371

Cited by 16 publications

(12 citation statements)

References 32 publications

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“…We attempted to estimate the carotenoid concentration in liposomes considering excitation energy transfer between TM-BODIPY and ECN and the data on carotenoids orientation in the membrane obtained from molecular dynamics simulations. To achieve this, we used the fact that there is an overlap between carotenoid absorption and TM-BODIPY emission spectra ( Figure 2 C for ECN and Figure 2 D for β-carotene), and probability of FRET between donor (fluorescent probe) and acceptor (carotenoid); suggesting TM-BODIPY in the absence of aggregation has the quantum yield = 0.95 (taken from [ 57 , 58 ]); assuming molar extinction coefficient of β-carotene being equal to 125,300 M −1 ·cm −1 and ECN to 75,300 M −1 ·cm −1 (data was taken from [ 59 ]); and setting the refractive index to 1.4251 for the soy lecithin emulsion environment (based on the data from [ 60 ]). Next, the orientation factor χ 2 between molecular transition dipole moments is usually used as 2/3 in randomly oriented systems, but in our case, there may be preferred orientations of carotenoid and fluorescence probe in the membrane.…”

Section: Resultsmentioning

confidence: 99%

“…This result cannot be related directly to the type of lecithin, as in general it does not influence the viscosity [ 63 ]. In addition, TM-BODIPY molecule propagates inside the lipid bilayer of nano-sized liposomes almost freely (according to molecular dynamic simulations visualized in Supplementary Video ) and at concentrations lower than 1 μM it is not prone to aggregation and heterooligomerization, which could have affected its fluorescence intensity and lifetime [ 58 ]. HomoFRET can affect θ values ( Supplementary Figure S2 ), but still it should not significantly alter experimental results on microviscosity since all the measurements were performed under the same conditions.…”

Section: Resultsmentioning

confidence: 99%

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Modulation of Membrane Microviscosity by Protein-Mediated Carotenoid Delivery as Revealed by Time-Resolved Fluorescence Anisotropy

et al. 2022

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Carotenoids are potent antioxidants with a wide range of biomedical applications. However, their delivery into human cells is challenging and relatively inefficient. While the use of natural water-soluble carotenoproteins capable to reversibly bind carotenoids and transfer them into membranes is promising, the quantitative estimation of the delivery remains unclear. In the present work, we studied echinenone (ECN) delivery by cyanobacterial carotenoprotein AnaCTDH (C-terminal domain homolog of the Orange Carotenoid Protein from Anabaena), into liposome membranes labelled with BODIPY fluorescent probe. We observed that addition of AnaCTDH-ECN to liposomes led to the significant changes in the fast-kinetic component of the fluorescence decay curve, pointing on the dipole-dipole interactions between the probe and ECN within the membrane. It may serve as an indirect evidence of ECN delivery into membrane. To study the delivery in detail, we carried out molecular dynamics modeling of the localization of ECN within the lipid bilayer and calculate its orientation factor. Next, we exploited FRET to assess concentration of ECN delivered by AnaCTDH. Finally, we used time-resolved fluorescence anisotropy to assess changes in microviscosity of liposomal membranes. Incorporation of liposomes with β-carotene increased membrane microviscosity while the effect of astaxanthin and its mono- and diester forms was less pronounced. At temperatures below 30 °C addition of AnaCTDH-ECN increased membrane microviscosity in a concentration-dependent manner, supporting the protein-mediated carotenoid delivery mechanism. Combining all data, we propose FRET-based analysis and assessment of membrane microviscosity as potent approaches to characterize the efficiency of carotenoids delivery into membranes.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Modulation of Membrane Microviscosity by Protein-Mediated Carotenoid Delivery as Revealed by Time-Resolved Fluorescence Anisotropy

et al. 2022

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“…This class of compounds makes it possible to obtain various functional derivatives and materials that can find application in various fields of chemistry and materials science. 54–64…”

Section: Compounds Based On Vin-d2-hmentioning

confidence: 99%

“…This class of compounds makes it possible to obtain various functional derivatives and materials that can find application in various fields of chemistry and materials science. [54][55][56][57][58][59][60][61][62][63][64] Thus, we chose stereoregular organocyclosilsesquioxane 20 as the starting compound (Fig. 6).…”

Section: Compounds Based On Stereoregular Cyclosilsesquioxane Vin-t 4 -Hmentioning

confidence: 99%

Sequential hydrothiolation–hydrosilylation: a route to the creation of new organosilicon compounds with preset structures

et al. 2023

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“…Recently, cyclosiloxanes having fluorescence moieties with appropriate linkers have been widely studied. Cycloteterasiloxane having naphthyl, anthryl, pyrenyl, − and BODIPY, with alkyl and alkenyl linkers have been prepared. However, cyclosiloxanes in which polycyclic aromatic hydrocarbons such as anthracene and pyrene are directly connected to silicon atoms have scarcely been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Cyclotri- and Tetrasiloxanes with Pyrenyl Groups

et al. 2022

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Cyclosiloxanes directly bearing polyaromatic groups on silicon atoms have scarcely been reported. Herein, hexa(1pyrenyl)cyclotrisiloxane (2) and octa(1-pyrenyl)cyclotetrasiloxane (3) were successfully prepared from di(1-pyrenyl)silanediol (1) in the presence of a weak base such as tetraethylammonium acetate and triethylamine in MeCN. The structure of the cyclosiloxanes bearing multiple pyrenyl groups in the solid and solution states was evaluated by NMR, X-ray crystallography, and density functional theory (DFT) calculations. All pyrenyl groups of 2 were oriented outward, and no π−π stacking of adjacent pyrenyl groups was observed. However, all pairs of adjacent pyrenyl groups at 1-and 3-positions in 3 are oriented in the same direction and were π−π stacked with respect to each other. The UV−vis spectra of 2 and 3 in organic solvents showed a slight broadening of the peaks, as observed for typical pyrene derivatives. Interestingly, the fluorescence spectra of 2 showed small monomer and strong excimer emissions; however, those of 3 showed only a strong excimer emission in all solvents. Partially pyrenylated cyclotri-and tetrasiloxanes (compounds 4 and 5) showed solvent-dependent monomer and excimer spectra as observed for di(1-pyrenyl)silane derivatives, implying that the excimer emissions of 2 and 3 arise from mainly geminal and vicinal pyrenyl groups, respectively.

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Modulation of the photophysical properties of multi-BODIPY-siloxane conjugates by varying the number of fluorophores

Cited by 16 publications

References 32 publications

Modulation of Membrane Microviscosity by Protein-Mediated Carotenoid Delivery as Revealed by Time-Resolved Fluorescence Anisotropy

Modulation of Membrane Microviscosity by Protein-Mediated Carotenoid Delivery as Revealed by Time-Resolved Fluorescence Anisotropy

Sequential hydrothiolation–hydrosilylation: a route to the creation of new organosilicon compounds with preset structures

Synthesis and Characterization of Cyclotri- and Tetrasiloxanes with Pyrenyl Groups

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