Novel synthetic approach to near-infrared heptamethine cyanine dyes and spectroscopic characterization in presence of biological molecules

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

doi:10.1016/j.jphotochem.2016.05.019

Cited by 18 publications

(10 citation statements)

References 49 publications

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“…More interesting is the fact of broadening of the absorption spectrum, which can be attributed to the dye aggregation on the DNA template [27]. Generally, the cyanine dyes interact with the DNA minor grooves forming the plane-to-plane H dimers that can be identified easily through the appearance of a new absorption band hypsochromically shifted with respect to the monomer band [20,32,33]. However, for some cyanine dyes the end-to-end aggregation in a minor groove of DNA was observed resulting in the emergence of a new bathochromically shifted absorption band [28,34,35].…”

Section: Resultsmentioning

confidence: 99%

“…Among a variety of fluorescent compounds currently used in the DNA and amyloid fibrils studies an important place belongs to the dyes of cyanine family [16][17][18][19][20]. To exemplify, the oxazole yellow homodimer, which has EEJP 2 2019 Olga Zhytniakivska, Uliana Tarabara et al…”

mentioning

confidence: 99%

“…previously been employed mainly as a DNA-intercalating probe, appeared to be suitable for in vitro amyloid sensing [16]. The ability to detect the protein fibrillar aggregates and to stain the double stranded DNA has been also shown for the mono-, tri-, penta-and heptamethine cyanine dye [17][18][19][20], styryl cyanine dyes [21,22], merocyanines [23], to name only a few. An extensive application of cyanines in the studies of amyloid fibrils and DNA is dictated by their favorable spectral properties, such as, particularly, high extinction coefficients, intensive absorption in a wide spectral region, from UV to NIR, high fluorescence intensity and quantum yield increase upon the dye binding to nucleic acids or proteins, etc.…”

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confidence: 99%

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Novel Phosphonium Dye TDV1 as a Potential Fluorescent Probe to Monitor DNA Interactions with Lysozyme Amyloid Fibrils

Zhytniakivska

Tarabara

Vus

et al. 2019

EEJP

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The applicability of the novel cationic phosphonium dye TDV1 to monitor the complexation between DNA and pathologically aggregated proteins, amyloid fibrils, was tested using the optical spectroscopy and molecular docking techniques. TDV1 has been found to be highly emissive in buffer solution and is characterized by one well-defined fluorescence peak attributed to the dye monomers. The association of the dye with the double stranded DNA was followed by the enhancement of monomer fluorescence coupled with a bathochromic shift of the emission maximum. The addition of fibrillar lysozyme (LzF) to TDV1-DNA mixture led to the further enhancement of fluorescence intensity of the monomeric dye form coupled with a hypsochromic shift of the emission maximum and an appearance of a second long-wavelength peak. An assumption has been made that the fluorescence enhancement augmenting with increasing the protein concentration in the TDV1/DNA system is produced by the interaction of the free TDV1 monomers with lysozyme fibrils as well as by the LzF-induced conformational alterations of DNA. The long-wavelength peak emerging in the presence of LzF is presumably a consequence of the J-aggregate formation upon the TDV1 association with lysozyme fibrils. The molecular docking studies showed that TDV1 monomers are incorporated into the fibril grooves associating with 7 β-strands in such a way that the dye long axis is parallel to the fibril axis. The most energetically favorable position of TDV1 is the S60-W62/G54-L56 groove in the lysozyme fibril core. In contrast, the TDV1 dimers seem to associate with the more hydrophilic side of the model β-sheet. Cumulatively, the results from the absorption and fluorescence measurements, together with the molecular docking analysis are consistent with the minor groove mode of the TDV1 binding to dsDNA. The electrostatic interactions seem to play a predominant role in the TDV1 complexation with the double stranded DNA, while the hydrophobic interactions and steric hindrances are supposed to be influential in the association of TDV1 with fibrillar lysozyme.

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Section: Resultsmentioning

confidence: 99%

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Novel Phosphonium Dye TDV1 as a Potential Fluorescent Probe to Monitor DNA Interactions with Lysozyme Amyloid Fibrils

Zhytniakivska

Tarabara

Vus

et al. 2019

EEJP

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“…Cyanine probes AK7-5 and AK7-6 ( Fig. 1) were synthesized in the University of Sofia, Bulgaria, as described previously [41]. Stock solutions of AK7-5 and AK7-6 were prepared by dissolving the dyes in dimethylsulfoxide (DMSO), then diluted by 5 mM sodium phosphate buffer (pH 7.4) and used for spectroscopic measurements.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

“…The concentration of the dyes was determined spectrophotometrically, using the extinction coefficients Preparation of amyloid fibrils. Amyloid fibrils were obtained from the egg yolk lysozyme by the protein incubation in 10 mM glycine buffer at pH 2 and 60 °C for 14 days [41]. Protein concentration in the stock solution was 10 mg/ml.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

Novel Cyanine Dyes as Potential Amyloid Probes: A Fluorescence Study

Tarabara

Vus

Kurutos

et al. 2018

EEJP

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The applicability of the novel heptamethine cyanine dyes AK7-5 and AK7-6 to the detection and characterization of one-dimensional protein aggregates (amyloid fibrils) associated with numerous pathologies has been evaluated using the method of fluorescence spectroscopy. It was found that both the monomeric and aggregated forms of these dyes can bind to amyloidogenic protein lysozyme, but the concomitant changes in the electronic structure of H-aggregates render them capable of fluorescing. The growth of the hypsochromic bands with negligible changes of the monomeric peaks induced by the native protein and the opposite effects induced by the lysozyme fibrils suggest that the native lysozyme has more binding sites for the dye aggregates than fibrillar protein, while the fibril grooves represent specific binding site for the dyes monomers. The observed spectral behavior of the cyanine dyes, viz. significant distinctions in the fluorescence responses produced by the monomeric and fibrillar forms of lysozyme, suggest the possibility of recruiting these compounds as fluorescent amyloid markers along with the classical amyloid marker Thioflavin T.За допомогою методу флуоресцентної спектроскопії проведена оцінка можливості використання нових гептаметинових ціанінових барвників AK7-5 та AK7-6 для детектування і характеризації одномірних білкових агрегатів (амілоїдних фібрил), пов'язаних із розвитком численних патологій. Показано, що мономерна та агрегована форми цих барвників можуть зв'язуватись з амілоїдогенним білком лізоцимом, а супутні зміни в електронній структурі Н-агрегатів надають їм здатності флуоресціювати. Зростання гіпсохромної смуги, поряд з незначними змінами мономерного піка, індуковані нативним білком, і протилежні ефекти, викликані фібрилами лізоциму, дозволяють припустити, шо нативний лізоцим має більшу кількість сайтів зв'язування для агрегатів барвника, ніж фібрилярна форма білка, в той час як жолобки фібрил являють собою специфічні сайти зв'язування для мономерів барвника. Спостережувана спектральна поведінка ціанінів, а саме значні відмінності флуоресцентних відповідей, що викликані мономерною та фібрилярною формами лізоциму, свідчать про можливість застосування цих сполук в якості флуоресцентних амілоїдних маркерів, поряд з класичним маркером Тіофлавіном Т. КЛЮЧОВІ СЛОВА: Гептаметинові ціанінові барвники, амілоїдний маркер, H-агрегати, флуоресценція, лізоцим, амілоїдні фібрили НОВЫЕ ЦИАНИНОВЫЕ КРАСИТЕЛИ КАК ПОТЕНЦИАЛЬНЫЕ АМИЛОИДНЫЕ ЗОНДЫ:

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Organic Dye Based Nanoparticles for Cancer Phototheranostics

Cai

Huang

et al. 2018

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236

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Phototheranostics, which simultaneously combines photodynamic and/or photothermal therapy with deep-tissue diagnostic imaging, is a promising strategy for the diagnosis and treatment of cancers. Organic dyes with the merits of strong near-infrared absorbance, high photo-to-radical and/or photothermal conversion efficiency, great biocompatibility, ready chemical structure fine-tuning capability, and easy metabolism, have been demonstrated as attractive candidates for clinical phototheranostics. These organic dyes can be further designed and fabricated into nanoparticles (NPs) using various strategies. Compared to free molecules, these NPs can be equipped with multiple synergistic functions and show longer lifetime in blood circulation and passive tumor-targeting property via the enhanced permeability and retention effect. In this article, the recent progress of organic dye-based NPs for cancer phototheranostic applications is summarized, which extends the anticancer arsenal and holds promise for clinical uses in the near future.

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Novel synthetic approach to near-infrared heptamethine cyanine dyes and spectroscopic characterization in presence of biological molecules

Cited by 18 publications

References 49 publications

Novel Phosphonium Dye TDV1 as a Potential Fluorescent Probe to Monitor DNA Interactions with Lysozyme Amyloid Fibrils

Novel Phosphonium Dye TDV1 as a Potential Fluorescent Probe to Monitor DNA Interactions with Lysozyme Amyloid Fibrils

Novel Cyanine Dyes as Potential Amyloid Probes: A Fluorescence Study

Organic Dye Based Nanoparticles for Cancer Phototheranostics

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