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Synthesis of New Styrylquinoline Cellular Dyes, Fluorescent Properties, Cellular Localization and Cytotoxic Behavior.

Rams-Baron M, Dulski M, Mrozek-Wilczkiewicz A, Korzec M, Cieslik W, Spaczyńska E, Bartczak P, Ratuszna A, Polanski J, Musiol R - PLoS ONE (2015)

Bottom Line: The spectroscopic properties of the compounds were measured and theoretical TD-DFT calculations were performed.All of the compounds that were studied appeared to be safe and indifferent to cells in a high concentration range.The presented results suggest that the quinoline compounds that were investigated in this study may be valuable structures for development as fluorescent dyes that could have biological applications.

View Article: PubMed Central - PubMed

Affiliation: A. Chelkowski Institute of Physics, University of Silesia, Uniwersytecka 4, Katowice, 40-007, Poland; Silesian Center for Education and Interdisciplinary Research, 75 Pulku Piechoty 1A, Chorzow, 41-500, Poland.

ABSTRACT
New styrylquinoline derivatives with their photophysical constants are described. The synthesis was achieved via Sonogashira coupling using the newly developed heterogeneous nano-Pd/Cu catalyst system, which provides an efficient synthesis of high purity products. The compounds were tested in preliminary fluorescent microscopy studies to in order to identify their preferable cellular localization, which appeared to be in the lipid cellular organelles. The spectroscopic properties of the compounds were measured and theoretical TD-DFT calculations were performed. A biological analysis of the quinolines that were tested consisted of cytotoxicity assays against normal human fibroblasts and colon adenocarcinoma cells. All of the compounds that were studied appeared to be safe and indifferent to cells in a high concentration range. The presented results suggest that the quinoline compounds that were investigated in this study may be valuable structures for development as fluorescent dyes that could have biological applications.

No MeSH data available.


Related in: MedlinePlus

The comparison of emission spectra of 1a in solvents of various polarity
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pone.0131210.g006: The comparison of emission spectra of 1a in solvents of various polarity

Mentions: The fluorescence quantum yield is one of the key parameters of fluorophores and permits a quantitative description of the fluorescence phenomenon. It is defined as the number of photons being emitted relative to the number of photons being absorbed. The quantum yields that were calculated are presented in Table 2. The strong influence of solvent on fluorescence emission was observed for 1a (Fig 6). Changing the solvent from DMSO to ethanol and chloroform led to a noticeable growth of fluorescence efficiency from 0.01 to 0.19 and 0.11, respectively. Among the compounds that were investigated, 3d had a significantly higher quantum efficiency than the others (e.g., 0.38 in chloroform), which means that incorporating an additional aromatic unit positively affects the fluorescent properties of a fluorophore. The same seems to be true for compounds 1a and 1b for which only a phenyl substituted structure revealed some fluorescent potency. This is in agreement with the general opinion about the nature of the fluorophoric properties of the aromatic core. Polycyclic systems and scaffolds packed with π conjugated bonds are the base of the most effective fluorophores. Recently, Yamaguchi and coworkers presented an apparent correlation between the structure of π conjugated hydrocarbons and their quantum yield of fluorescence [32]. According to that report, both the fluorescence emission maximum and quantum yield are higher in longer π conjugation in an S1 state. Namely, the longer the linear donor/acceptor conjugated dipole the better its fluorescent properties. The compounds that were tested, although unsubstituted on account of their biological indifference, should follow this rule to some extent. To evaluate this, we performed some additional calculations as follows.


Synthesis of New Styrylquinoline Cellular Dyes, Fluorescent Properties, Cellular Localization and Cytotoxic Behavior.

Rams-Baron M, Dulski M, Mrozek-Wilczkiewicz A, Korzec M, Cieslik W, Spaczyńska E, Bartczak P, Ratuszna A, Polanski J, Musiol R - PLoS ONE (2015)

The comparison of emission spectra of 1a in solvents of various polarity
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4482625&req=5

pone.0131210.g006: The comparison of emission spectra of 1a in solvents of various polarity
Mentions: The fluorescence quantum yield is one of the key parameters of fluorophores and permits a quantitative description of the fluorescence phenomenon. It is defined as the number of photons being emitted relative to the number of photons being absorbed. The quantum yields that were calculated are presented in Table 2. The strong influence of solvent on fluorescence emission was observed for 1a (Fig 6). Changing the solvent from DMSO to ethanol and chloroform led to a noticeable growth of fluorescence efficiency from 0.01 to 0.19 and 0.11, respectively. Among the compounds that were investigated, 3d had a significantly higher quantum efficiency than the others (e.g., 0.38 in chloroform), which means that incorporating an additional aromatic unit positively affects the fluorescent properties of a fluorophore. The same seems to be true for compounds 1a and 1b for which only a phenyl substituted structure revealed some fluorescent potency. This is in agreement with the general opinion about the nature of the fluorophoric properties of the aromatic core. Polycyclic systems and scaffolds packed with π conjugated bonds are the base of the most effective fluorophores. Recently, Yamaguchi and coworkers presented an apparent correlation between the structure of π conjugated hydrocarbons and their quantum yield of fluorescence [32]. According to that report, both the fluorescence emission maximum and quantum yield are higher in longer π conjugation in an S1 state. Namely, the longer the linear donor/acceptor conjugated dipole the better its fluorescent properties. The compounds that were tested, although unsubstituted on account of their biological indifference, should follow this rule to some extent. To evaluate this, we performed some additional calculations as follows.

Bottom Line: The spectroscopic properties of the compounds were measured and theoretical TD-DFT calculations were performed.All of the compounds that were studied appeared to be safe and indifferent to cells in a high concentration range.The presented results suggest that the quinoline compounds that were investigated in this study may be valuable structures for development as fluorescent dyes that could have biological applications.

View Article: PubMed Central - PubMed

Affiliation: A. Chelkowski Institute of Physics, University of Silesia, Uniwersytecka 4, Katowice, 40-007, Poland; Silesian Center for Education and Interdisciplinary Research, 75 Pulku Piechoty 1A, Chorzow, 41-500, Poland.

ABSTRACT
New styrylquinoline derivatives with their photophysical constants are described. The synthesis was achieved via Sonogashira coupling using the newly developed heterogeneous nano-Pd/Cu catalyst system, which provides an efficient synthesis of high purity products. The compounds were tested in preliminary fluorescent microscopy studies to in order to identify their preferable cellular localization, which appeared to be in the lipid cellular organelles. The spectroscopic properties of the compounds were measured and theoretical TD-DFT calculations were performed. A biological analysis of the quinolines that were tested consisted of cytotoxicity assays against normal human fibroblasts and colon adenocarcinoma cells. All of the compounds that were studied appeared to be safe and indifferent to cells in a high concentration range. The presented results suggest that the quinoline compounds that were investigated in this study may be valuable structures for development as fluorescent dyes that could have biological applications.

No MeSH data available.


Related in: MedlinePlus