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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.


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Structures of the quinoline derivatives.
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pone.0131210.g001: Structures of the quinoline derivatives.

Mentions: In our group, quinoline derivatives are being broadly investigated for their chemistry [9,10] and possible applications [11–13]. These researches have resulted in some highly active anticancer [14,15] and antifungal [16] agents. In the present study, we describe the structural, electronic and optical properties of novel styrylquinolines and their simple analogs. The concept of the design of quinoline dyes is depicted in Fig 1. It combines the alkyne analogs of 1a-b and styrylquinolines with an elongated lipophilic chain 3a-d.


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)

Structures of the quinoline derivatives.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0131210.g001: Structures of the quinoline derivatives.
Mentions: In our group, quinoline derivatives are being broadly investigated for their chemistry [9,10] and possible applications [11–13]. These researches have resulted in some highly active anticancer [14,15] and antifungal [16] agents. In the present study, we describe the structural, electronic and optical properties of novel styrylquinolines and their simple analogs. The concept of the design of quinoline dyes is depicted in Fig 1. It combines the alkyne analogs of 1a-b and styrylquinolines with an elongated lipophilic chain 3a-d.

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