Spectroscopic and In Vitro Investigations of Boron(III) Complex with Meso-4-Methoxycarbonylpropylsubstituted Dipyrromethene for Fluorescence Bioimaging Applications

Molecules. 2020 Oct 3;25(19):4541. doi: 10.3390/molecules25194541.

Abstract

This study focuses on the behavior of a new fluorescent marker for labeling individual biomolecules and staining cell organelles developed on a meso-substituted BODIPY platform. Boron(III) complex with meso-4-methoxycarbonylpropylsubstituted 3,3',5,5'-tetramethyl-2,2'-dipyrromethene has been synthesized and identified via visible, UV-, NMR- and MS-spectra X-ray. The behavior of fluorophore in solutions has been studied with various experimental techniques. It has been found that luminophore exhibits a high quantum yield (almost ~100-75%) in the blue-green region (513-520 nm) and has high photostability. In addition, biological analysis indicates that the fluorophore exhibits a tendency to effectively penetrate into cell membranes. On the other hand, the proposed BODIPY can be used to study the significant differences among a large number of pathogens of mycotic infections, as well as to visualize structural changes in the plasma membrane, which is necessary for the clearance of mammalian cells undergoing apoptotic cell death.

Keywords: BODIPY; biomarker; dipyrromethene; fluorophore; pathogenic microorganisms.

MeSH terms

  • Boron / chemistry*
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry
  • Candida albicans / cytology
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Diagnostic Imaging*
  • Doxorubicin / pharmacology
  • Electrons
  • Fusarium / cytology
  • Humans
  • Porphobilinogen / analogs & derivatives*
  • Porphobilinogen / chemistry
  • Solvents / chemistry
  • Spectrometry, Fluorescence
  • Subcellular Fractions / metabolism
  • Ultraviolet Rays

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Solvents
  • dipyrromethene
  • Porphobilinogen
  • Doxorubicin
  • Boron

Supplementary concepts

  • Fusarium oxysporum