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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

UV-VIS absorption (A) and normalized fluorescence (B) spectra of styrylquinolines solutions in DMSO.
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pone.0131210.g005: UV-VIS absorption (A) and normalized fluorescence (B) spectra of styrylquinolines solutions in DMSO.

Mentions: The emission spectra of the compounds that were synthesized covered the colors from violet to blue. For 1a in the DMSO solution, the maximum fluorescence emission was observed in the ultraviolet region (λem = 367 nm) while for the others the maximum was blue-shifted and was observed in the visible region of the electromagnetic spectrum (λem = 407–411 nm, see Fig 5-B). For solvents that had a lower polarity, the emission maxima were slightly shifted towards shorter wavelengths. In the case of 1b the weak fluorescence emission was observed only for solutions prepared in ethanol.


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)

UV-VIS absorption (A) and normalized fluorescence (B) spectra of styrylquinolines solutions in DMSO.
© Copyright Policy
Related In: Results  -  Collection

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

pone.0131210.g005: UV-VIS absorption (A) and normalized fluorescence (B) spectra of styrylquinolines solutions in DMSO.
Mentions: The emission spectra of the compounds that were synthesized covered the colors from violet to blue. For 1a in the DMSO solution, the maximum fluorescence emission was observed in the ultraviolet region (λem = 367 nm) while for the others the maximum was blue-shifted and was observed in the visible region of the electromagnetic spectrum (λem = 407–411 nm, see Fig 5-B). For solvents that had a lower polarity, the emission maxima were slightly shifted towards shorter wavelengths. In the case of 1b the weak fluorescence emission was observed only for solutions prepared in ethanol.

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