Spectroscopic and nonlinear optical properties of new chalcone fluorescent probes for bioimaging applications: a theoretical and experimental study

J Mol Model. 2016 Jun;22(6):125. doi: 10.1007/s00894-016-2990-4. Epub 2016 May 11.

Abstract

In this study, the newly synthesized non-centrosymmetric, 4-dimethylamino-3'-isothiocyanatochalcone (PKA) compound was presented. This compound belongs to the chalcone group, and its main purpose is to be used in biomedical imaging as a fluorescence dye. For this reason, the linear and nonlinear properties in solvents of different polarity were thoroughly studied. In accordance with the requirements for a fluorochrome, the PKA compound is characterized by strong absorption, large Stokes' shifts, relatively high fluorescence quantum yields and high nonlinear optical response. Moreover, the isothiocyanate reactive probe was conjugated with Concanavalin A. Conventional fluorescence microscopy imaging of Candida albicans cells incubated with the PKA-Concanavalin A, is presented. The results of this study show that the novel conjugate PKA-Concanavalin A could be a promising new probe for cellular labelling in biological and biomedical research. Graphical abstract Spectroscopic behavior of the PKA dye.

Keywords: Density functional theory; Electronic excited states; Fluorescence bioimaging; Fluorochrome; Solvatochromism; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Algorithms
  • Candida albicans / metabolism
  • Chalcones / chemical synthesis
  • Chalcones / chemistry*
  • Chalcones / pharmacokinetics
  • Concanavalin A / chemistry
  • Concanavalin A / pharmacokinetics
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / pharmacokinetics
  • Microscopy, Fluorescence / methods*
  • Models, Chemical
  • Models, Molecular
  • Molecular Structure
  • Solvents / chemistry
  • Spectrometry, Fluorescence / methods*

Substances

  • Chalcones
  • Fluorescent Dyes
  • Solvents
  • Concanavalin A