Novel aminobenzanthrone dyes for amyloid fibril detection

Vus, Kateryna; Trusova, Valeriya; Gorbenko, Galyna; Kirilova, Elena; Kirilov, G; Kalnina, Inta; Kinnunen, Paavo K.J.

doi:10.1016/j.cplett.2012.02.061

Cited by 17 publications

(10 citation statements)

References 32 publications

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“…Because of this, the fluorescent emission depends on the excitation wavelength, and the molecules that are distributed in different micro-solvation domains can be selectively excited. This effect, where the emission maximum changes due to a change in the excitation, is called the “red excitation edge”, and it is observed in a variety of fluorescent probes [ 112 ], such as TNS [ 113 ] and aminobenzanthrone dyes (λex = 450–490 nm, λem = 560–640 nm, range depending on the dye) [ 114 ]. This phenomenon was used with Nile Red to analyze gliadin at pH 3.0 and 7.0.…”

Section: Fluorescence Spectroscopy Is a Versatile Tool For Evaluatmentioning

confidence: 99%

Evaluation of Peptide/Protein Self-Assembly and Aggregation by Spectroscopic Methods

2020

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The self-assembly of proteins is an essential process for a variety of cellular functions including cell respiration, mobility and division. On the other hand, protein or peptide misfolding and aggregation is related to the development of Parkinson’s disease and Alzheimer’s disease, among other aggregopathies. As a consequence, significant research efforts are directed towards the understanding of this process. In this review, we are focused on the use of UV-Visible Absorption Spectroscopy, Fluorescence Spectroscopy and Circular Dichroism to evaluate the self-organization of proteins and peptides in solution. These spectroscopic techniques are commonly available in most chemistry and biochemistry research laboratories, and together they are a powerful approach for initial as well as routine evaluation of protein and peptide self-assembly and aggregation under different environmental stimulus. Furthermore, these spectroscopic techniques are even suitable for studying complex systems like those in the food industry or pharmaceutical formulations, providing an overall idea of the folding, self-assembly, and aggregation processes, which is challenging to obtain with high-resolution methods. Here, we compiled and discussed selected examples, together with our results and those that helped us better to understand the process of protein and peptide aggregation. We put particular emphasis on the basic description of the methods as well as on the experimental considerations needed to obtain meaningful information, to help those who are just getting into this exciting area of research. Moreover, this review is particularly useful to those out of the field who would like to improve reproducibility in their cellular and biomedical experiments, especially while working with peptide and protein systems as an external stimulus. Our final aim is to show the power of these low-resolution techniques to improve our understanding of the self-assembly of peptides and proteins and translate this fundamental knowledge in biomedical research or food applications.

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Section: Fluorescence Spectroscopy Is a Versatile Tool For Evaluatmentioning

confidence: 99%

Evaluation of Peptide/Protein Self-Assembly and Aggregation by Spectroscopic Methods

2020

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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%

“…Staneva et al also demonstrated a good antimicrobial activity against the Gram-positive B. cereus and the yeasts C. lipolytica bacteria for the dendrimers modified with eight fluorescent benzanthrone chromophore units [12]. A good deal of studies indicate that benzanthrone dyes can be used as effective microenvironmental sensors for monitoring structural changes in biological systems [2][3][4][5][6][7][8][9][10][11][12][13][14]. In particular, the benzanthrone derivatives were employed in DNA [8], protein [4][5][6] and membrane studies [7,9,10,13].…”

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confidence: 99%

“…Moreover, the spectral responses of some benzanthrone dyes in different lipid systems have been shown to correlate with the degree of lipid bilayer hydration [9], rendering these probes highly suitable for examining the membrane-related processes, especially those coupled with the changes in membrane polarity [7]. The applicability of the novel benzanthrones is not limited to the membrane studies since these dyes are extensively used in the protein research field, for instance, in the studies of a particular class of protein aggregates, amyloid fibrils [4][5][6][7]. Specifically, it has been shown previously that aminobenzanthrones are capable of distinguishing between the native monomeric and fibrillar protein states, surpassing the classical amyloid marker ThT in the sensitivity to the lysozyme amyloid fibrils [3,4,6].…”

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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 aminobenzanthrone dyes for amyloid fibril detection

Cited by 17 publications

References 32 publications

Evaluation of Peptide/Protein Self-Assembly and Aggregation by Spectroscopic Methods

Evaluation of Peptide/Protein Self-Assembly and Aggregation by Spectroscopic Methods

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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