Environmentally sensitive fluorescence of the topical retinoid adapalene

Intrinsic fluorescence of drugs brings valuable information on their localization in the organism and their interaction with key biomolecules. In this work, we investigate the absorption and emission properties of the topical retinoid adapalene in different solvents and biological media. While the U...

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Detalles Bibliográficos
Autores: Soler-Orenes, JA, Monari, A, Miranda, MA, Hernández-Gil, J, Lhiaubet-Vallet, V
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:INCLIVA
Repositorio:r-INCLIVA. Repositorio Institucional de Producción Científica de INCLIVA
OAI Identifier:oai:incliva.fundanetsuite.com:p19224
Acceso en línea:https://incliva.portalinvestigacion.com/publicaciones/19224
Access Level:acceso abierto
Palabra clave:albumin
DNA
micelles
micropolarity
steady-state fluorescence
topical drug
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spelling Environmentally sensitive fluorescence of the topical retinoid adapaleneSoler-Orenes, JAMonari, AMiranda, MAHernández-Gil, JLhiaubet-Vallet, ValbuminDNAmicellesmicropolaritysteady-state fluorescencetopical drugIntrinsic fluorescence of drugs brings valuable information on their localization in the organism and their interaction with key biomolecules. In this work, we investigate the absorption and emission properties of the topical retinoid adapalene in different solvents and biological media. While the UVA/UVB absorption band does not exhibit any significant solvent-dependent behavior, a strong positive solvatochromism is observed for the emission. These results are in line with molecular modeling and simulations that show the presence of two quasi-degenerate states, i.e., a local pi-pi* and an intermolecular charge-transfer (ICT) state. However, molecular modeling also revealed that, whatever the solvent, at the corresponding equilibrium geometry the lowest and emissive excited state is the local pi-pi*. Finally, the potential of adapalene to act as a biological probe is demonstrated using albumin, DNA and micelles.FRONTIERS MEDIA SA2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttps://incliva.portalinvestigacion.com/publicaciones/19224Frontiers in ChemistryISSN: 22962646reponame:r-INCLIVA. Repositorio Institucional de Producción Científica de INCLIVAinstname:INCLIVAInglésinfo:eu-repo/semantics/openAccessoai:incliva.fundanetsuite.com:p192242026-06-07T16:35:31Z
dc.title.none.fl_str_mv Environmentally sensitive fluorescence of the topical retinoid adapalene
title Environmentally sensitive fluorescence of the topical retinoid adapalene
spellingShingle Environmentally sensitive fluorescence of the topical retinoid adapalene
Soler-Orenes, JA
albumin
DNA
micelles
micropolarity
steady-state fluorescence
topical drug
title_short Environmentally sensitive fluorescence of the topical retinoid adapalene
title_full Environmentally sensitive fluorescence of the topical retinoid adapalene
title_fullStr Environmentally sensitive fluorescence of the topical retinoid adapalene
title_full_unstemmed Environmentally sensitive fluorescence of the topical retinoid adapalene
title_sort Environmentally sensitive fluorescence of the topical retinoid adapalene
dc.creator.none.fl_str_mv Soler-Orenes, JA
Monari, A
Miranda, MA
Hernández-Gil, J
Lhiaubet-Vallet, V
author Soler-Orenes, JA
author_facet Soler-Orenes, JA
Monari, A
Miranda, MA
Hernández-Gil, J
Lhiaubet-Vallet, V
author_role author
author2 Monari, A
Miranda, MA
Hernández-Gil, J
Lhiaubet-Vallet, V
author2_role author
author
author
author
dc.subject.none.fl_str_mv albumin
DNA
micelles
micropolarity
steady-state fluorescence
topical drug
topic albumin
DNA
micelles
micropolarity
steady-state fluorescence
topical drug
description Intrinsic fluorescence of drugs brings valuable information on their localization in the organism and their interaction with key biomolecules. In this work, we investigate the absorption and emission properties of the topical retinoid adapalene in different solvents and biological media. While the UVA/UVB absorption band does not exhibit any significant solvent-dependent behavior, a strong positive solvatochromism is observed for the emission. These results are in line with molecular modeling and simulations that show the presence of two quasi-degenerate states, i.e., a local pi-pi* and an intermolecular charge-transfer (ICT) state. However, molecular modeling also revealed that, whatever the solvent, at the corresponding equilibrium geometry the lowest and emissive excited state is the local pi-pi*. Finally, the potential of adapalene to act as a biological probe is demonstrated using albumin, DNA and micelles.
publishDate 2024
dc.date.none.fl_str_mv 2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://incliva.portalinvestigacion.com/publicaciones/19224
url https://incliva.portalinvestigacion.com/publicaciones/19224
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv FRONTIERS MEDIA SA
publisher.none.fl_str_mv FRONTIERS MEDIA SA
dc.source.none.fl_str_mv Frontiers in Chemistry
ISSN: 22962646
reponame:r-INCLIVA. Repositorio Institucional de Producción Científica de INCLIVA
instname:INCLIVA
instname_str INCLIVA
reponame_str r-INCLIVA. Repositorio Institucional de Producción Científica de INCLIVA
collection r-INCLIVA. Repositorio Institucional de Producción Científica de INCLIVA
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812455

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