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PET-Driven Fluorescence Modulation in Halochromic Styryl Hemicyanine Dyes Targeting DNA Minor Groove.

Teodora Aleksandrova1, Aleksandar Pashev1, Sonia Ilieva2

  • 1Department of Chemistry and Biochemistry, Faculty of Pharmacy, Medical University Pleven, 1 St. Kliment Ohridski Street, 5800 Pleven, Bulgaria.

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Summary

New fluorescent dyes with phenylpiperazine groups show pH-responsive fluorescence for DNA detection. These styryl hemicyanine dyes are halochromic and exhibit photoinduced electron transfer effects, making them potential probes for nucleic acid environments.

Keywords:
DFTPET effectdsDNAmolecular dockingsolvatochromismstyryl hemicyanine

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Biophysical Chemistry

Background:

  • Development of novel fluorescent probes is crucial for biological and chemical sensing.
  • Styryl hemicyanine dyes are known for their tunable photophysical properties.
  • Understanding dye-DNA interactions is key for developing diagnostic tools.

Purpose of the Study:

  • Synthesize and characterize new styryl hemicyanine dyes with N-phenylpiperazine end groups.
  • Investigate the photophysical properties of these dyes in various solvents and when bound to DNA.
  • Explore their potential as pH-responsive fluorescent probes for nucleic acids.

Main Methods:

  • Green synthesis of styryl hemicyanine dyes.
  • Spectroscopic techniques (UV/VIS, fluorescence) to study solvatochromism and DNA binding.
  • Circular dichroism spectroscopy and molecular docking for interaction analysis.
  • Quantum chemical calculations (DFT, TDDFT) for theoretical insights.

Main Results:

  • Dyes exhibit strong negative solvatochromism and fluorescence quenching upon DNA binding.
  • Pronounced fluorescent acidochromism and photoinduced electron transfer (PET) effect observed.
  • Acid titration of dye-DNA complexes restores fluorescence, suppressing PET and rigidifying the structure.
  • Interaction modes with DNA elucidated through spectroscopic and computational methods.

Conclusions:

  • The synthesized dyes are halochromic and pH-responsive.
  • Suppression of PET and structural rigidification are key to fluorescence restoration.
  • These dyes show significant potential as pH-responsive fluorescent probes for nucleic acid environments.