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

[Image: see text] 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...

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Autores principales: Felip-León, Carles, Angulo-Pachón, César A., Miravet, Juan F., Galindo, Francisco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6643459/
https://www.ncbi.nlm.nih.gov/pubmed/31458209
http://dx.doi.org/10.1021/acsomega.8b01869
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author Felip-León, Carles
Angulo-Pachón, César A.
Miravet, Juan F.
Galindo, Francisco
author_facet Felip-León, Carles
Angulo-Pachón, César A.
Miravet, Juan F.
Galindo, Francisco
author_sort Felip-León, Carles
collection PubMed
description [Image: see text] 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/O(2) induces deamination of the ANI fluorophore, resulting in nonemissive 1,8-naphtalimide derivatives. It is found that the reactivity toward NO/O(2) is regulated by the different aggregation modes presented by the molecules in aqueous medium. In this way, the molecules displaying fluorescence response toward NO/O(2) are those with weak self-association properties whereas the compound with a high hydrophobic character (self-assembling into large nanoparticles) is insensitive to this species. Ultimately, the results described here could not only set the basis for the design of fluorescent bioprobes for NO/O(2) based on ANI derivatives or other monoamino compounds but also could raise awareness about the importance of supramolecular interactions for the design of chemosensors.
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spelling pubmed-66434592019-08-27 Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing Felip-León, Carles Angulo-Pachón, César A. Miravet, Juan F. Galindo, Francisco ACS Omega [Image: see text] 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/O(2) induces deamination of the ANI fluorophore, resulting in nonemissive 1,8-naphtalimide derivatives. It is found that the reactivity toward NO/O(2) is regulated by the different aggregation modes presented by the molecules in aqueous medium. In this way, the molecules displaying fluorescence response toward NO/O(2) are those with weak self-association properties whereas the compound with a high hydrophobic character (self-assembling into large nanoparticles) is insensitive to this species. Ultimately, the results described here could not only set the basis for the design of fluorescent bioprobes for NO/O(2) based on ANI derivatives or other monoamino compounds but also could raise awareness about the importance of supramolecular interactions for the design of chemosensors. American Chemical Society 2018-11-15 /pmc/articles/PMC6643459/ /pubmed/31458209 http://dx.doi.org/10.1021/acsomega.8b01869 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Felip-León, Carles
Angulo-Pachón, César A.
Miravet, Juan F.
Galindo, Francisco
Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing
title Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing
title_full Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing
title_fullStr Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing
title_full_unstemmed Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing
title_short Self-Assembly Controls Reactivity with Nitric Oxide: Implications for Fluorescence Sensing
title_sort self-assembly controls reactivity with nitric oxide: implications for fluorescence sensing
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6643459/
https://www.ncbi.nlm.nih.gov/pubmed/31458209
http://dx.doi.org/10.1021/acsomega.8b01869
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