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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

Molecular orbitals of the five quinoline derivatives obtained at the TD-B3LYP/6-31+G(d,p) theory level.
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pone.0131210.g007: Molecular orbitals of the five quinoline derivatives obtained at the TD-B3LYP/6-31+G(d,p) theory level.

Mentions: In the case of 1b the low intensity experimental bands corresponded with the theoretical bands due to the S0→S3 and S0→S4 electronic transitions, while the most intensive experimental bands (not reflected by theory) would be associated with S0→S1 and S0→S2. It is noteworthy that the isosurfaces of the HOMO and LUMO orbitals are localized through the central double bond and the double bonds of the rings in all of the molecules (Fig 7), while LUMO distribution is also localized on the nitrogen.


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)

Molecular orbitals of the five quinoline derivatives obtained at the TD-B3LYP/6-31+G(d,p) theory level.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0131210.g007: Molecular orbitals of the five quinoline derivatives obtained at the TD-B3LYP/6-31+G(d,p) theory level.
Mentions: In the case of 1b the low intensity experimental bands corresponded with the theoretical bands due to the S0→S3 and S0→S4 electronic transitions, while the most intensive experimental bands (not reflected by theory) would be associated with S0→S1 and S0→S2. It is noteworthy that the isosurfaces of the HOMO and LUMO orbitals are localized through the central double bond and the double bonds of the rings in all of the molecules (Fig 7), while LUMO distribution is also localized on the nitrogen.

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