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

ABSTRACT: Three molecules containing the fluorophore 4-amino-1,8-naphthalimide (ANI) and showing different tendencies to self-assembly in aqueous environment have been prepared and fully characterized. The fluorescence emissions of two of these compounds in aqueous solutions are efficiently quenched in the presence of nitric oxide (NO) in aerated medium. Nuclear magnetic resonance and mass spectrometry techniques indicate that NO/O₂ induces deamination of the ANI fluorophore, resulting in nonemissive 1,8-naphtalimide derivatives. It is found that the reactivity toward NO/O₂ is regulated by the different aggregation modes presented by the molecules in aqueous medium. In this way, the molecules displaying fluorescence response toward NO/O₂ are those with weak self-asso

SUBMITTER: Felip-Leon C 

PROVIDER: S-EPMC6643459 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature