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Naphthalimide-based macrophage nucleus imaging probes.

Francisco Fueyo-González1, Mar Fernández-Gutiérrez2, Diego García-Puentes3

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European Journal of Medicinal Chemistry
|June 9, 2020
PubMed
Summary

Chemical modifications of naphthalimide fluorophores alter their photophysical properties. These novel fluorophores serve as effective macrophage nucleus imaging probes with low cytotoxicity in human cancer cells.

Keywords:
DNA intercalantsFluorescence probesMacrophage imaging probesNaphthalimide derivativesQuinolimide derivatives

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Area of Science:

  • Organic chemistry
  • Photophysics
  • Biomedical imaging

Background:

  • Naphthalimide derivatives are versatile fluorophores with tunable photophysical properties.
  • Chemical modifications offer a route to fine-tune solvatochromic behavior and sensing capabilities.

Purpose of the Study:

  • To investigate how substituent modifications on naphthalimide scaffolds affect their photophysical properties, specifically solvatochromism.
  • To develop novel naphthalimide-based fluorophores for macrophage nucleus imaging.
  • To evaluate the DNA-binding and cytotoxicity profiles of these new probes.

Main Methods:

  • Synthesis of naphthalimide derivatives with varying substituents at position 6.
  • Spectroscopic analysis to determine photophysical properties, including solvatochromism.
  • Evaluation of DNA-binding affinity and cytotoxicity in human cancer cell lines.

Main Results:

  • Replacing a methoxy (OMe) group with diverse amines modulated the intramolecular charge transfer (ICT) character, enhancing solvatochromic effects in some derivatives.
  • Similar modifications in other analogues (PET fluorophores) reduced or reversed solvent polarity sensitivity.
  • The developed fluorophores demonstrated effective binding to DNA as intercalants and exhibited low cytotoxicity.

Conclusions:

  • Chemical tuning of naphthalimide substituents provides a powerful strategy to control photophysical properties and develop targeted imaging agents.
  • These naphthalimide-based fluorophores show promise as macrophage nucleus imaging probes with favorable safety profiles for potential biomedical applications.