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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

Hydrolysis of compound 3b.
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pone.0131210.g003: Hydrolysis of compound 3b.

Mentions: Compounds 3a, 3b, 3d were obtained according to the standard method [9, 10, 30] from quinaldine and aldehydes 2a-c in acetic anhydride, while aldehydes 2b-c were obtained in the Sonogashira coupling in heterogeneous conditions on a nano-Pd catalyst. For the preparation of the bimetallic catalyst 5% Pd/Cu, we modified a previously described method [18].The overall activity of the nano-particle catalysts depends mainly on the effectiveness of the distribution of the metallic grains in the matrix [31]. The bimetallic nano-Pd/Cu was obtained by digesting the carrier in nano-Pd/silica and transferring the nanoparticles on to the electrolytic copper. We found that digestion of the material dispersed in an excess of the NaOH resulted in a shortened time of the procedure and reduced the temperature. Such prepared nanoparticles of the catalyst retain their high activity[18]. This catalytic system provided us with quantitative conversions. Compound 3c was obtained through the hydrolysis of 3b immediately after its synthesis as is shown in Fig 3. All of the compounds that were obtained were characterized using NMR and mass spectroscopy.


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)

Hydrolysis of compound 3b.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0131210.g003: Hydrolysis of compound 3b.
Mentions: Compounds 3a, 3b, 3d were obtained according to the standard method [9, 10, 30] from quinaldine and aldehydes 2a-c in acetic anhydride, while aldehydes 2b-c were obtained in the Sonogashira coupling in heterogeneous conditions on a nano-Pd catalyst. For the preparation of the bimetallic catalyst 5% Pd/Cu, we modified a previously described method [18].The overall activity of the nano-particle catalysts depends mainly on the effectiveness of the distribution of the metallic grains in the matrix [31]. The bimetallic nano-Pd/Cu was obtained by digesting the carrier in nano-Pd/silica and transferring the nanoparticles on to the electrolytic copper. We found that digestion of the material dispersed in an excess of the NaOH resulted in a shortened time of the procedure and reduced the temperature. Such prepared nanoparticles of the catalyst retain their high activity[18]. This catalytic system provided us with quantitative conversions. Compound 3c was obtained through the hydrolysis of 3b immediately after its synthesis as is shown in Fig 3. All of the compounds that were obtained were characterized using NMR and mass spectroscopy.

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