Novel Benzanthrone Aminoderivatives for Membrane Studies

Trusova, Valeriya; Kirilova, Elena; Kalnina, Inta; Kirilov, G; Zhytniakivska, Olga; Fedorov, Pavel V.; Gorbenko, Galyna

doi:10.1007/s10895-011-1035-8

Cited by 18 publications

(25 citation statements)

References 18 publications

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“…Later, several benzanthrone dyes were synthesized to verify changes in the physicochemical properties of a lipid bilayer (Trusova et al, 2012;Ryzhova et al, 2016), and to identify and characterize fibrillar aggregates of lysozyme (Vus et al, 2014).…”

Section: Discussionmentioning

confidence: 99%

“…Bright fluorescence, high extinction coefficient, photo-, thermo-and chemical stability, and reduced background signal make benzanthrone dyes particularly attractive as bio-imaging agents (Yang et al, 1999). Our previous study demonstrated high lipidassociating ability of a series of newly synthesized benzanthrone amino and amidino derivatives (Trusova et al, 2012;.…”

Section: Introductionmentioning

confidence: 98%

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Novel luminescent dyes for confocal laser scanning microscopy used in parasite Trematoda diagnostics*

et al. 2018

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Benzanthrone derivates are now widely used in many industrial and scientific applications as dyes for polymers and textiles. In biochemical, biomedical and diagnostics investigations benzanthrone dyes are used as a lipophilic fluorescent probe since many benzanthrone derivates demonstrate bright fluorescence and they have ability to intercalate between membrane lipids. The aim of research presented here was to assess the luminescence ability of benzanthrone derivatives using microscopic visualization of biological objects. Accordingly, specimens of freshwater trematodes: Diplostomum spathaceum, Diplodiscus subclavatus and Prosotocus confusus, were stained by novel benzanthrone dyes using different fixatives. The samples were examined under a confocal laser scanning microscope. All of the dyes tested demonstrated good results for digestive and reproductive system visualization. Based on obtained results we conclude that benzanthrone dyes could be used for internal and external structure confocal laser scanning microscopic imaging of trematode specimens.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Novel luminescent dyes for confocal laser scanning microscopy used in parasite Trematoda diagnostics*

et al. 2018

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“…Despite wide technological utilization of these compounds, their applicability as fluorescent probes in biological assays (amyloid fibril identification, cell membrane and DNA structure investigation) is continuously growing . Therefore, it is very important to synthesize new benzanthrone class compounds and to investigate their physicochemical properties.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical study on structure and spectroscopic properties of 2‐bromo‐3‐N‐(N′,N′‐dimethylformamidino) benzanthrone

et al. 2018

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The goal of present research is a theoretical and experimental investigation of geometrical structure, electronic properties, absorption and fluorescence spectra prediction for 2-bromo-3-N-(N',N'-dimethylformamidino)benzanthrone. As a result of conformational analysis, two rotamers have been found with a rotational barrier of 5.45 kcal/mol. Absorption and fluorescence spectra maxima in the solvent (ethanol) have been calculated using the concepts of the Jablonsky diagram. The obtained values of the absorption and fluorescence maxima (437 and 679 nm, respectively) correspond to the experimental values (447 and 659 nm). The abnormally large Stokes shift is associated with the redistribution of electron density, as well as flattening of the structure of the molecule in the excited state. According to the frontal molecular orbital analysis data, the peak in the long-wave part of the absorption spectra is created by an electron transition from the highest occupied molecular orbital (HOMO) to the lowest occupied molecular orbital (LUMO) (π→π*). Substitute group does not participate in the formation of absorption and fluorescence spectra.

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“…The benzanthrone dyes, a well-known class of fluorescent probes that emit in the spectral region from yellow-green to red-purple (depending on the dye structure), have found diverse applications in biomedical research and diagnostics due to their favorable spectral characteristics, such as a large extinction coefficient, a marked Stokes shift; negligible fluorescence in an aqueous phase, etc [1][2][3][4][5][6][7][8][9][10]. Specifically, it has been shown that the benzanthrone dye in combination with the thin polylactic acid film is capable of displaying the antimicrobial activity against Gram-positive and Gramnegative bacteria [11].…”

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confidence: 99%

Molecular Dynamics Simulation of the Interaction Between Benzanthrone Dye and Model Lipid Membranes

Zhytniakivska

2020

EEJP

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The benzanthrone fluorescent dyes are known as environmentally-sensitive reporters for exploring the physicochemical properties and structural alterations of lipid membranes. In the present work the 100-ns molecular dynamics simulation (MD) was used to characterize the bilayer location and the nature of interactions between the benzanthrone fluorescent dye ABM and the model lipid membranes composed of the zwitterionic lipid phosphatidylcholine (PC) and its mixtures with the anionic lipid phosphatidylglycerol (PG20) and sterol cholesterol (Chol30). The MD simulations were performed in the CHARMM36m force field using the GROMACS package. The ABM molecule, which was initially placed at a distance of 30 Å from the midplane of the lipid bilayer, after 10 ns of simulation was found to be completely incorporated into the membrane interior and remained within the lipid bilayer for the rest of the simulation time. The analysis of the MD simulation results showed that the lipid bilayer location of the benzanthrone dye ABM depends on the membrane composition, with the distance from bilayer center being gradually shifted from 0.78 nm in the neat PC bilayer to 0.95 nm and 1.5 nm in the PG- and Chol-containing membranes, respectively. In addition, the partitioning of the ABM into the neat PC bilayer was followed by the probe translocation from the outer membrane leaflet to the inner one. A separate series of MD simulations was aimed at examining the ABM influence on the lipid bilayer structure. It was found that ABM partitioning into the lipid bilayers of various composition has no significant effect on the orientation of the fatty acid chains and leads only to a small increase of the deuterium order parameter for the carbon atoms 5-to-8 in the sn-2 acyl chains of the neat PC membranes. In addition, the interaction of the ABM with the model lipid membranes caused the slight decrease of the surface area per lipid pointing to the slight increase of the packing density of lipid molecules in the presence of ABM. The results obtained provide a basis for deeper understanding of the membrane interactions of benzanthrone dyes and may be useful for the design of the novel fluorescent probes for membrane studies.

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Novel Benzanthrone Aminoderivatives for Membrane Studies

Cited by 18 publications

References 18 publications

Novel luminescent dyes for confocal laser scanning microscopy used in parasite Trematoda diagnostics*

Novel luminescent dyes for confocal laser scanning microscopy used in parasite Trematoda diagnostics*

Experimental and theoretical study on structure and spectroscopic properties of 2‐bromo‐3‐N‐(N′,N′‐dimethylformamidino) benzanthrone

Molecular Dynamics Simulation of the Interaction Between Benzanthrone Dye and Model Lipid Membranes

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