Symmetric Meso-Chloro-Substituted Pentamethine Cyanine Dyes Containing Benzothiazolyl/Benzoselenazolyl Chromophores Novel Synthetic Approach and Studies on Photophysical Properties upon Interaction with bio-Objects

Kurutos, Atanas; Ryzhova, Olga; Trusova, Valeriya; Gorbenko, Galyna; Gadjev, Nikolai; Deligeorgiev, Todor

doi:10.1007/s10895-015-1700-4

Cited by 24 publications

(9 citation statements)

References 38 publications

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“…Cyanine dyes represent a remarkable class of organic compounds, which have found numerous applications in theranostic of tumors [26,27] and fluorescence imaging of biomolecules [28,29] due to their: i) high extinction coefficients; ii) high affinity for biomolecules; iii) longwave absorption and emission bands (near-infrared compounds), enabling highly sensitive in vivo measurements due to the absence of the autofluorescence of the biological molecules in this region, etc. [30,31].…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Cyanine dyes derived inhibition of insulin fibrillization

Vus

Girych

Trusova

et al. 2019

Journal of Molecular Liquids

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The potential of novel cyanine dyes to inhibit the insulin amyloid formation was evaluated using thioflavin T fluorescence assay, quantum-chemical calculations, molecular docking and molecular dynamics simulations. According to the ability to suppress the insulin fibrillization under physiological conditions the examined compounds were found to follow the order: trimethines > pentamethines > monomethines > heptamethines. Of these, the trimethines 3-3 and 3-5, and pentamethines 5-3 and 5-9 almost completely prevented the protein aggregation by retarding both nucleation (except 3-3) and elongation processes. The quantum-chemical calculations revealed a complex relationship between the dye structure and its inhibitory effects.The molecular docking studies showed that most cyanines bind specifically to the L17 ladder of the B chain, located at the dry steric zipper of the insulin fibril protofilament, and form the stable complexes with the helices of the insulin monomer. The molecular dynamics simulations provided evidence for the increase of insulin helicity in the presence of cyanines. Collectively, the presented findings highlight two possible mechanisms by which cyanines can inhibit the insulin fibrillization: i) stabilization of the native protein structure followed by the retardation of the protein nucleation (all dyes); and ii) blocking the lateral extension of β-sheets via the dye-protein stacking interactions (3-3, 3-5, 5-3, 5-9). Overall, the obtained results may prove of importance for the design of small molecules capable of preventing amyloid fibril formation by insulin and other proteins.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Cyanine dyes derived inhibition of insulin fibrillization

Vus

Girych

Trusova

et al. 2019

Journal of Molecular Liquids

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“…In recent years, structurally diversified low molecular weight derivatives that are able to recognize and delineate tiny structural distinctions of DNA/RNA have attracted increasing interest, due to their various potential applications in many areas [1][2][3][4][5]. Therefore, the design and discovery of new low molecular weight molecules targeting DNA/RNA has been a subject of extensive studies.…”

Section: Introduction Figure 1 Structures Of the Studied Dabco-cyaninmentioning

confidence: 99%

Cell penetrating, mitochondria targeting multiply charged DABCO-cyanine dyes

et al. 2018

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Unless otherwise stated, all starting materials and solvents required for the synthesis of the DABCO cyanine dyes were purchased from Sigma-Aldrich, Organica Feinchemie GmbH Wolfen, Fluka, Alfa-Aesar, TCI Europe, Deutero GmbH, and used without any further purification. The solvents used for the spectroscopic analyses were purchased form Macron Fine Chemicals TM. All other starting materials and solvents were commercial products of analytical grade and were used without further purification. 2.2 Synthesis and spectroscopic analysis of the dyes 2.3. Analysis methods and equipment All products were characterized using various spectroscopic techniques. The progress of the reactions was monitored employing TLC (Merck F 254 silica gel; chloroform: methanol: acetic acid-80:15:5). Recrystallization from methanol yielded analytical samples of the title cyanines. 1 H-NMR and APT-NMR spectra of the compounds were recorded on a Brucker Avance III 500 MHz instrument in DMSO-d6 at room temperature. Chemical shifts were reported in ppm in δ-values with respect to tetramethylsilane (TMS) as an internal reference, or the corresponding peak of the deuterated solvent. Coupling constants JH-H were expressed in Hz. The structures of all intermediates were also evaluated on the target cyanine dyes. Melting point temperatures were evaluated on a Kofler bench and are uncorrected. Absorption and steady state fluorescence spectra of the unbound dyes were recorded in methanol solutions at room temperature, using 10-mm path-length quartz cuvettes on a Cecil Aurius CE 3021 UV-Vis spectrophotometer and Perkin Elmer LS45 fluorescence spectrometer (fixed slits 10-10 nm) at room temperature. 2.4. Synthetic approach to the DABCO monomethine cyanines and intermediate products 2.4.1. Preparation of intermediates 2a-2c

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“…Our previous studies revealed that the novel mono-and pentamethine cyanine compounds can be effectively employed as non-covalent labels for nucleic acids [17,19,20]. As a next logical step, herein we directed our efforts towards evaluating the DNA-and RNA-binding ability of the novel trimethine cyanine dye with an emphasis on its use in the drug-displacement studies.…”

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Competitive Binding of Novel Cyanine Dye AK3-5 and Europium Coordination Complexes to DNA

Zhytniakivska

Zabrudska

Tarabara

et al. 2019

EEJP

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The present study was undertaken to assess the applicability of the novel trimethine cyanine dye AK3-5 as a competitive ligand for the antitumor agents, Eu(III) coordination complexes (EC), in the DNA-containing systems, using the displacement assay as an analytical instrument. The analysis of fluorescence spectra revealed a strong association of AK3-5 with nucleic acids, with the strength of interaction being higher for the double stranded DNA, compared to the single-stranded RNA. The binding parameters of the cyanine dye have been determined in terms of the McGhee & von Hippel neighbouring site-exclusion model and a classical Langmuir model. The AK3-5 association constant in the presence of DNA was found to be equal to 5.1×104 M-1, which is consistent to those of the well-known DNA intercalators. In turn, the binding of the cyanine to the RNA was characterized by a significantly lower association constant ( ~ 3.4×103 M-1) indicating either the external or “partially intercalated” binding mode. The addition of the europium complexes to the AK3-5-DNA system was followed by the fluorescence intensity decrease, with a magnitude of this effect being dependent on the EC structure. The observed fluorescence decrease of AK3-5 in the presence of europium complexes V7 and V9 points to the competition between the cyanine dye and antitumor drugs for the DNA binding sites. The dependencies of the AK3-5-DNA fluorescence intensity decrease vs. europium complex concentration were analyzed in terms of the Langmuir adsorption model, giving the values of the drug association constant equal to 5.4×104 M-1and 3.9×105 M-1 for the europium complexes V7 and V9, respectively. A more pronounced decrease of the AK3-5 fluorescence in the presence of V5 and V10 was interpreted in terms of the drug-induced quenching of the dye fluorescence, accompanying the competition between AK3-5 and Eu(III) complexes for the DNA binding sites. Cumulatively, the results presented here strongly suggest that AK3-5 can be effectively used in the nucleic acid studies and in the dye-drug displacement assays.

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Symmetric Meso-Chloro-Substituted Pentamethine Cyanine Dyes Containing Benzothiazolyl/Benzoselenazolyl Chromophores Novel Synthetic Approach and Studies on Photophysical Properties upon Interaction with bio-Objects

Cited by 24 publications

References 38 publications

Cyanine dyes derived inhibition of insulin fibrillization

Cyanine dyes derived inhibition of insulin fibrillization

Cell penetrating, mitochondria targeting multiply charged DABCO-cyanine dyes

Competitive Binding of Novel Cyanine Dye AK3-5 and Europium Coordination Complexes to DNA

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