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Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels

The activity of ion channels can be reversibly photo-controlled via the binding of molecular photoswitches, often based on an azobenzene scaffold. Those azobenzene derivatives interact with aromatic residues of the protein via stacking interactions. In the present work, the effect of face-to-face an...

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Autores principales: Palmisano, Vito F., Faraji, Shirin, Nogueira, Juan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10696555/
https://www.ncbi.nlm.nih.gov/pubmed/36883995
http://dx.doi.org/10.1039/d2cp05678j
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author Palmisano, Vito F.
Faraji, Shirin
Nogueira, Juan J.
author_facet Palmisano, Vito F.
Faraji, Shirin
Nogueira, Juan J.
author_sort Palmisano, Vito F.
collection PubMed
description The activity of ion channels can be reversibly photo-controlled via the binding of molecular photoswitches, often based on an azobenzene scaffold. Those azobenzene derivatives interact with aromatic residues of the protein via stacking interactions. In the present work, the effect of face-to-face and t-shaped stacking interactions on the excited state electronic structure of azobenzene and p-diaminoazobenzene integrated into the Na(V)1.4 channel is computationally investigated. The formation of a charge transfer state, caused by electron transfer from the protein to the photoswitches, is observed. This state is strongly red shifted when the interaction takes place in a face-to-face orientation and electron donating groups are present on the aromatic ring of the amino acids. The low-energy charge transfer state can interfere with the photoisomerization process after excitation to the bright state by leading to the formation of radical species.
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spelling pubmed-106965552023-12-06 Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels Palmisano, Vito F. Faraji, Shirin Nogueira, Juan J. Phys Chem Chem Phys Chemistry The activity of ion channels can be reversibly photo-controlled via the binding of molecular photoswitches, often based on an azobenzene scaffold. Those azobenzene derivatives interact with aromatic residues of the protein via stacking interactions. In the present work, the effect of face-to-face and t-shaped stacking interactions on the excited state electronic structure of azobenzene and p-diaminoazobenzene integrated into the Na(V)1.4 channel is computationally investigated. The formation of a charge transfer state, caused by electron transfer from the protein to the photoswitches, is observed. This state is strongly red shifted when the interaction takes place in a face-to-face orientation and electron donating groups are present on the aromatic ring of the amino acids. The low-energy charge transfer state can interfere with the photoisomerization process after excitation to the bright state by leading to the formation of radical species. The Royal Society of Chemistry 2023-02-28 /pmc/articles/PMC10696555/ /pubmed/36883995 http://dx.doi.org/10.1039/d2cp05678j Text en This journal is © the Owner Societies https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Palmisano, Vito F.
Faraji, Shirin
Nogueira, Juan J.
Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels
title Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels
title_full Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels
title_fullStr Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels
title_full_unstemmed Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels
title_short Effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels
title_sort effect of stacking interactions on charge transfer states in photoswitches interacting with ion channels
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10696555/
https://www.ncbi.nlm.nih.gov/pubmed/36883995
http://dx.doi.org/10.1039/d2cp05678j
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