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

PLoS One. 2015 Jun 26;10(6):e0131210. doi: 10.1371/journal.pone.0131210. eCollection 2015.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cytotoxins* / chemical synthesis
  • Cytotoxins* / chemistry
  • Cytotoxins* / pharmacology
  • Fluorescent Dyes* / chemical synthesis
  • Fluorescent Dyes* / chemistry
  • Fluorescent Dyes* / pharmacology
  • Humans
  • Quinolines* / chemical synthesis
  • Quinolines* / chemistry
  • Quinolines* / pharmacology

Substances

  • Cytotoxins
  • Fluorescent Dyes
  • Quinolines
  • styrylquinoline

Grants and funding

This study was supported by NCN—National center for science grants 2014/13/D/NZ7/00322 (AMW), 2012/07/N/NZ7/02110 (WC), 2013/09/B/NZ700423 (RM) and DEC-2012/07/N/ST5/02221 (MD); National Research and Development Center (NCBiR) Grant ORGANOMET no: PBS2/A5/40/2014. This research was supported in part by PL-Grid Infrastructure.