New series of non-toxic DNA intercalators, mitochondria targeting fluorescent dyes

Kurutos, Atanas; Orehovec, Iva; Paić, Ana Tomašić; Crnolatac, Ivo; Horvat, Lucija; Gadjev, Nikolai; Piantanida, Ivo; Deligeorgiev, Todor

doi:10.1016/j.dyepig.2017.09.049

Cited by 22 publications

(11 citation statements)

References 22 publications

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“…Brilliant fluorescence denotation of the mitochondria even at low concentrations of A and B1 dyes, absence of photobleaching effect and relative safety for the cell homeostasis, marks this two dyes as promising fluorescent markers for live cell imaging. Our previous live cell fluorescent imaging dyes [18,19] were also based on oxazole yellow or thiazole orange scaffold bearing usually two positive charges. We added multiple charges to increase the water solubility and selectively accumulate the compounds in the mitochondria, while the other substituents were designed to keep the impact on cell proliferation minimal.…”

Section: A B1mentioning

confidence: 99%

“…Encouraged by our previous research efforts in design of specific mitochondrial fluorescent probes based on benzoxazolium and benzothiazolium derived dicationic monomethine cyanine dyes [17][18][19], we have prepared new series of lipophilic cyanine dyes equipped with several cationic quaternary ammonium moieties. This was achieved by introducing DABCO within the structures.…”

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

confidence: 99%

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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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Section: A B1mentioning

confidence: 99%

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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“…As the mechanism of mitochondrial uptake relates to all small molecules targeting mitochondria, it will be deliberated in more detail in a separate section. Figure 2 shows commonly used, commercially available compounds [27,28] and some of the mitochondrial probes designed, synthesised and investigated in collaboration with partners in our laboratory [29][30][31].…”

Section: Fluorescent Probes Targeting Mitochondriamentioning

confidence: 99%

Getting Charged for the Mitochondrial Uptake

Crnolatac¹

2020

Fluorescence Methods for Investigation of Living Cells and Microorganisms

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Mitochondria are hot! First of all, literally. Recent results showed that locally in the functional human mitochondria, the temperature rises close to 50°C. The research was based on the thermosensitive fluorescent dye that targets mitochondria. Figuratively, mitochondria are even hotter, in terms of undergoing research exploring their role in energy production, cell signalling, programmed cell death and biosynthesis. Fluorescent probes and dyes are not restricted only to imaging of these fascinating organelles; they are used to monitor the mitochondrial membrane potential, pH and the redox status. The membrane potential is essential in the process of ATP production as it constitutes more than 80% of electrochemical proton motive force used in this process. Thus, observing mitochondrial membrane potential is crucial in most of the mitochondrial research. This imaging should usually be performed with minimal invasiveness and damage to the mitochondria and mitochondrial function. There are only a few fluorescent probes for mitochondrial membrane potential monitoring currently in use as valuable indicators of cells' functional status. Those probes show varying degrees of interference with cell or mitochondrial metabolism and photo-induced damage. In this chapter, the characteristics, advantages and disadvantages of such probes will be discussed. The mechanisms of uptake of these fluorescent probes will be explained.

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“…A wide range of biological and biomedical systems currently being studied with the use of spectral fluorescent probes stimulates a permanent emergence of research aimed at developing new efficient and selective dye probes for the detection and staining of biomolecules in such systems (see, e.g., [ 16 , 17 , 18 ]). There are a large number of works by different research groups devoted to the synthesis and spectral fluorescent study of various MCDs (symmetrical and unsymmetrical) in order to develop probes for nucleic acids [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ]. There are also some works directed to the study of primary photophysical and photochemical processes in MCD molecules, both free and noncovalently bound to nucleic acids [ 35 , 36 , 37 , 38 , 39 , 40 ] (see also the review [ 41 ]).…”

Section: Introductionmentioning

confidence: 99%

Photonics of Some Monomethine Cyanine Dyes in Solutions and in Complexes with Biomolecules

Pronkin,

Tatikolov

2023

IJMS

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In search of new probes for biomolecules, the spectral fluorescent study of four monomethine cyanine dyes (MCD), both unsymmetrical and symmetrical, has been carried out in different organic solvents, in aqueous buffer solutions, and in the presence of DNA and HSA. The complexation of MCD with biomacromolecules leads to a steep growth of the fluorescence intensity. Complexes of MCD with dsDNA and HSA of various types were modeled in silico by molecular docking. Experiments on thermal dissociation of dsDNA in the presence of MCD showed the formation of intercalative complexes of MCD with DNA. Quenching of intrinsic fluorescence of HSA by MCD occurred with rate constants much higher than the diffusion limit, that is, in dye–HSA complexes. Effective constants of MCD complexation with the biomacromolecules were estimated. MCD 1 has the best characteristics as a possible fluorescent probe for dsDNA and can serve as a sensitive and selective probe for dsDNA in the presence of HSA. Photochemical properties of MCD complexed with DNA have been also studied. An increase in the quantum yield of the triplet states of MCD in complexes with DNA has been found, which may be important for using these dyes as potential candidates in photodynamic therapy.

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New series of non-toxic DNA intercalators, mitochondria targeting fluorescent dyes

Cited by 22 publications

References 22 publications

Cell penetrating, mitochondria targeting multiply charged DABCO-cyanine dyes

Cell penetrating, mitochondria targeting multiply charged DABCO-cyanine dyes

Getting Charged for the Mitochondrial Uptake

Photonics of Some Monomethine Cyanine Dyes in Solutions and in Complexes with Biomolecules

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