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Area of Science:

  • Organic Chemistry
  • Biochemistry
  • Chemical Biology

Background:

  • Boron-dipyrromethene (BODIPY) dyes are widely used fluorescent probes.
  • Developing stable and reactive fluorescent labeling reagents is crucial for biomolecule detection.
  • Mesoionic compounds offer unique electronic and chemical properties.

Purpose of the Study:

  • To synthesize novel BODIPY mesoionic acid fluorides.
  • To evaluate their utility as water-stable electrophilic reagents for fluorescent derivatization.
  • To develop a fluorogenic probe for imaging fungal pathogens.

Main Methods:

  • Synthesis of BODIPY mesoionic acid fluorides via an isocyanide multicomponent reaction.
  • Assessment of water stability and reactivity under mild conditions.
  • Fluorescent labeling of the antifungal natamycin.
  • Testing the derived probe for imaging fungal pathogens and differentiating from bacterial cells.

Main Results:

  • Successful preparation of novel BODIPY mesoionic acid fluorides.
  • Demonstrated water stability and reactivity with amines under mild, activation-free conditions.
  • Efficient fluorescent labeling of natamycin.
  • Development of a selective fluorogenic probe for human and plant fungal pathogens, distinguishing them from bacteria.

Conclusions:

  • BODIPY mesoionic acid fluorides are versatile, water-stable reagents for fluorescent labeling.
  • The developed probe shows high selectivity for fungal pathogens, enabling targeted imaging.
  • This work expands the toolkit for fluorescent probes in chemical biology and diagnostics.