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Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing.

Carles Felip-León1, César A Angulo-Pachón1, Juan F Miravet1

  • 1Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat s/n, 12071 Castellón, Spain.

ACS Omega
|August 29, 2019
PubMed
Summary

New fluorescent probes using 4-amino-1,8-naphthalimide (ANI) derivatives show potential for nitric oxide (NO) detection. Their reactivity is influenced by self-assembly, with less aggregated molecules effectively sensing NO.

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Area of Science:

  • Supramolecular Chemistry
  • Fluorescent Chemosensors
  • Materials Science

Background:

  • 4-amino-1,8-naphthalimide (ANI) derivatives are known fluorophores.
  • Nitric oxide (NO) plays crucial roles in biological systems.
  • Self-assembly behavior can influence molecular properties and reactivity.

Purpose of the Study:

  • To synthesize and characterize ANI derivatives with varying self-assembly tendencies.
  • To investigate the fluorescence response of these compounds to nitric oxide (NO) in the presence of oxygen (O2).
  • To understand how self-assembly affects the sensing mechanism of ANI-based probes for NO.

Main Methods:

  • Synthesis and full characterization of three ANI-containing molecules.
  • Fluorescence spectroscopy to monitor probe response in aqueous solutions.
  • Nuclear magnetic resonance (NMR) and mass spectrometry to elucidate reaction mechanisms.

Main Results:

  • Two ANI derivatives exhibited efficient fluorescence quenching upon exposure to NO/O2.
  • The quenching mechanism involves NO/O2-induced deamination of the ANI fluorophore.
  • Sensing capability is dependent on aggregation: weakly self-assembling molecules are responsive, while highly aggregated ones are insensitive.

Conclusions:

  • The study establishes a link between molecular aggregation and the reactivity of ANI fluorophores towards NO/O2.
  • Results provide a foundation for designing novel fluorescent NO/O2 bioprobes based on ANI or similar structures.
  • Highlights the critical role of supramolecular chemistry in developing effective chemosensors.