Azaindole-BODIPYs: Synthesis, fluorescent recognition of hydrogen sulfate anion and biological evaluation

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Apr 15:213:73-82. doi: 10.1016/j.saa.2019.01.047. Epub 2019 Jan 16.

Abstract

The synthesized and sensing capability of two novel azaindole substituted mono and distyryl BODIPY dyes against bisulfate anion were reported. Structural characterizations of the targeted compounds were conducted by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, 1H and 13C NMR spectroscopies. Photophysical properties of the azaindole substituted BODIPY compounds were investigated employing absorption and fluorescence spectroscopies in acetonitrile solution. It was found that the final compounds 3 and 4 exhibited exclusively selective and sensitive turn-off sensor behavior on HSO4- anion. Additionally, the stoichiometry ratio of the targeted compounds to bisulfate anion was measured 0.5 by Job's method. Also, density function theory was performed to the optical response of the sensor for targeted compounds. Furthermore, the cytotoxicity of Azaindole-BODIPYs was examined against living human leukemia K562 cell lines.

Keywords: Anionsensor; Azaindole; Borondipyrromethenes; Chemosensor; DFT; Fluorescence; Hydrogen sulfate; K562 cell lines.

MeSH terms

  • Anions / analysis*
  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Calibration
  • Cell Survival
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Inhibitory Concentration 50
  • K562 Cells
  • Molecular Conformation
  • Spectrometry, Fluorescence
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Static Electricity
  • Sulfuric Acids / analysis*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Anions
  • Boron Compounds
  • Indoles
  • Sulfuric Acids
  • sulfuric acid