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Ketoprofen Recognition and Sensing by Zn(II) Complexes with Fluorogenic Triamine Receptors.

Yschtar Tecla Simonini Steiner1, Liviana Mummolo2, Rania Zartit1

  • 1Dipartimento di Chimica "Ugo Schiff", Università degli Studi di Firenze, Via della Lastruccia 3, Sesto Fiorentino, 50019 Firenze, Italy.

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Two novel ligands, L1 and L2, form fluorescent zinc complexes. These complexes bind ketoprofen, altering fluorescence through photoinduced electron transfer and cation π interactions, impacting drug delivery applications.

Keywords:
NSAIDs detectionanion bindinganthracenefluorescent receptorsketoprofenmolecular dynamics simulationssupramolecular chemistryzinc complexes

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Area of Science:

  • Coordination Chemistry
  • Supramolecular Chemistry
  • Fluorescent Sensors

Background:

  • Fluorescent polyamine receptors often suffer from fluorescence quenching via photoinduced electron transfer (PET).
  • Designing ligands that modulate PET is crucial for developing effective fluorescent sensors and drug delivery systems.

Purpose of the Study:

  • To synthesize and characterize novel ligands (L1 and L2) incorporating triamine moieties and anthracene fluorophores.
  • To investigate the coordination behavior of these ligands with Zn(II) ions.
  • To explore the influence of Zn(II) binding and subsequent ketoprofen (KP) complexation on the fluorescence properties of the ligands.

Main Methods:

  • Synthesis of diethylenetriamine (L1) and dipropylenetriamine (L2) based ligands.
  • Formation and characterization of Zn(II) complexes.
  • Spectroscopic studies (fluorescence) to analyze metal ion and drug binding.
  • Computational modeling including ab initio calculations and molecular dynamics simulations.

Main Results:

  • Stable 1:1 Zn(II) complexes with L1 and L2 were formed, with metal coordination by all ligand nitrogens.
  • Zn(II) binding to L1 enhanced fluorescence by inhibiting PET; Zn(II) binding to L2 caused quenching due to cation π interactions.
  • Ternary complexes with ketoprofen ([KPZnL]+ and [(KP)2ZnL]) were formed.
  • Ketoprofen binding enhanced L2 fluorescence but slightly reduced L1 fluorescence, again attributed to cation π contacts.

Conclusions:

  • Ligand structure dictates the photophysical response upon Zn(II) and ketoprofen binding.
  • The interplay between PET inhibition and cation π interactions governs fluorescence modulation.
  • These findings offer insights into the design of responsive fluorescent materials for sensing and potential therapeutic applications.