Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity

The interest in the photochromism and functional applications of donor-acceptor Stenhouse adducts (DASAs) soared in recent years owing to their outstanding advantages and flexible design. However, their low solubility and irreversible conversion in aqueous solutions hampered exploring DASAs for biol...

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Autores: Castagna, Rossella, Maleeva, Galyna, Pirovano, Deborah, Matera, Carlo, Gorostiza Langa, Pablo Ignacio
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2022
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/188733
Acceso en línea:https://hdl.handle.net/2445/188733
Access Level:acceso abierto
Palabra clave:Fototeràpia
Neurotransmissors
Neurologia
Farmacologia
Phototherapy
Neurotransmitters
Neurology
Pharmacology
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spelling Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal ActivityCastagna, RossellaMaleeva, GalynaPirovano, DeborahMatera, CarloGorostiza Langa, Pablo IgnacioFototeràpiaNeurotransmissorsNeurologiaFarmacologiaPhototherapyNeurotransmittersNeurologyPharmacologyThe interest in the photochromism and functional applications of donor-acceptor Stenhouse adducts (DASAs) soared in recent years owing to their outstanding advantages and flexible design. However, their low solubility and irreversible conversion in aqueous solutions hampered exploring DASAs for biology and medicine. It is notably unknown whether the barbiturate electron acceptor group retains the pharmacological activity of drugs such as phenobarbital, which targets γ-aminobutyric acid (GABA)-type A receptors (GABAARs) in the brain. Here, we have developed the model compound DASA-barbital based on a scaffold of red-switching second-generation DASAs, and we demonstrate that it is active in GABAARs and alters the neuronal firing rate in a physiological medium at neutral pH. DASA-barbital can also be reversibly photoswitched in acidic aqueous solutions using cyclodextrin, an approved ingredient of drug formulations. These findings clarify the path toward the biological applications of DASAs and to exploit the versatility displayed in polymers and materials science.2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/188733Articles publicats en revistes (Institut de Bioenginyeria de Catalunya (IBEC))reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésversió postprint del document publicat a: https://doi.org/10.1021/jacs.2c04920Journal of The American Chemical Society, 2022, vol. 144, num. 34, p. 15595-15602https://doi.org/10.1021/jacs.2c04920info:eu-repo/grantAgreement/EC/H2020/712754(c) ACS, 2022http://creativecommons.org/licenses/by/3.0/es/info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1887332026-05-27T06:46:51Z
dc.title.none.fl_str_mv Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
title Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
spellingShingle Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
Castagna, Rossella
Fototeràpia
Neurotransmissors
Neurologia
Farmacologia
Phototherapy
Neurotransmitters
Neurology
Pharmacology
title_short Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
title_full Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
title_fullStr Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
title_full_unstemmed Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
title_sort Donor-Acceptor Stenhouse Adduct Displaying Reversible Photoswitching in Water and Neuronal Activity
dc.creator.none.fl_str_mv Castagna, Rossella
Maleeva, Galyna
Pirovano, Deborah
Matera, Carlo
Gorostiza Langa, Pablo Ignacio
author Castagna, Rossella
author_facet Castagna, Rossella
Maleeva, Galyna
Pirovano, Deborah
Matera, Carlo
Gorostiza Langa, Pablo Ignacio
author_role author
author2 Maleeva, Galyna
Pirovano, Deborah
Matera, Carlo
Gorostiza Langa, Pablo Ignacio
author2_role author
author
author
author
dc.subject.none.fl_str_mv Fototeràpia
Neurotransmissors
Neurologia
Farmacologia
Phototherapy
Neurotransmitters
Neurology
Pharmacology
topic Fototeràpia
Neurotransmissors
Neurologia
Farmacologia
Phototherapy
Neurotransmitters
Neurology
Pharmacology
description The interest in the photochromism and functional applications of donor-acceptor Stenhouse adducts (DASAs) soared in recent years owing to their outstanding advantages and flexible design. However, their low solubility and irreversible conversion in aqueous solutions hampered exploring DASAs for biology and medicine. It is notably unknown whether the barbiturate electron acceptor group retains the pharmacological activity of drugs such as phenobarbital, which targets γ-aminobutyric acid (GABA)-type A receptors (GABAARs) in the brain. Here, we have developed the model compound DASA-barbital based on a scaffold of red-switching second-generation DASAs, and we demonstrate that it is active in GABAARs and alters the neuronal firing rate in a physiological medium at neutral pH. DASA-barbital can also be reversibly photoswitched in acidic aqueous solutions using cyclodextrin, an approved ingredient of drug formulations. These findings clarify the path toward the biological applications of DASAs and to exploit the versatility displayed in polymers and materials science.
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/188733
url https://hdl.handle.net/2445/188733
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv versió postprint del document publicat a: https://doi.org/10.1021/jacs.2c04920
Journal of The American Chemical Society, 2022, vol. 144, num. 34, p. 15595-15602
https://doi.org/10.1021/jacs.2c04920
info:eu-repo/grantAgreement/EC/H2020/712754
dc.rights.none.fl_str_mv (c) ACS, 2022
http://creativecommons.org/licenses/by/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) ACS, 2022
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv Articles publicats en revistes (Institut de Bioenginyeria de Catalunya (IBEC))
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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