Environmentally sensitive fluorescence of the topical retinoid adapalene

[EN] 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...

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Detalles Bibliográficos
Autores: Soler-Orenes, Juan A., Monari, Antonio, Miranda, Miguel A., Hernández-Gil, Javier, Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universitat Politècnica de València (UPV)
Repositorio:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
Idioma:inglés
OAI Identifier:oai:riunet.upv.es:10251/209229
Acceso en línea:https://riunet.upv.es/handle/10251/209229
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, Juan A.Monari, AntonioMiranda, Miguel A.Hernández-Gil, JavierLhiaubet, Virginie Lyria|||0000-0002-8205-8892AlbuminDNAMicellesMicropolaritySteady-state fluorescenceTopical drug[EN] 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.The author(s) declare that financial support was received for the research, authorship, and/or publication of this article. Financial support from the Spanish (project PID 2021-128348NB-I00 funded by MCIN/AEI/10.13039/501100011033/and FEDER a way of making Europe, and Severo Ochoa centre of excellence program CEX 2021-001230-S) and regional (CIAICO/2021/061) governments is acknowledged. AM also thanks ANR and CGI for their financial support of this work through Labex SEAM ANR 11 LABX 086, ANR 11 IDEX 05 02. The support of the IdEx Université Paris 2019 ANR-18-IDEX-0001. JS-O is also thankful to the Spanish Government for the predoctoral grant (PRE 2019-089665). JH-G thanks the support of the Maria Zambrano Program of Excellence within the framework of grants for talent retaining of the Universitat Politecnica de Valencia and the Spanish Ministry of Universities, funded by the European Union-Next Generation (UPV Contract C16684).Frontiers Media SAInstituto Universitario Mixto de Tecnología QuímicaEuropean CommissionGeneralitat ValencianaMinisterio de UniversidadesAgencia Estatal de InvestigaciónEuropean Regional Development FundUniversitat Politècnica de ValènciaAgence Nationale de la Recherche, FranciaRepositorio Institucional de la Universitat Politècnica de València Riunet20242024-07-08journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://riunet.upv.es/handle/10251/209229reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valénciainstname:Universitat Politècnica de València (UPV)InglésengAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2021-128348NB-I00 TRANSFERENCIA DE ENERGIA TRIPLETE-TRIPLETE A LARGA DISTANCIA EN SISTEMAS MODELO DE ADNAgence Nationale de la Recherche, Francia https://doi.org/10.13039/501100001665 ANR-18-IDEX-0001 Université de ParisAgence Nationale de la Recherche, Francia https://doi.org/10.13039/501100001665 ANR-11-LABX-0086Agence Nationale de la Recherche, Francia https://doi.org/10.13039/501100001665 ANR-11-IDEX-05-02Generalitat Valenciana https://doi.org/10.13039/501100003359 CIAICO%2F2021%2F061Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 CEX2021-001230-SAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 PRE 2019-089665open accesshttp://purl.org/coar/access_right/c_abf2Reconocimiento (by)http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:riunet.upv.es:10251/2092292026-06-13T07:49:27Z
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, Juan A.
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, Juan A.
Monari, Antonio
Miranda, Miguel A.
Hernández-Gil, Javier
Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
author Soler-Orenes, Juan A.
author_facet Soler-Orenes, Juan A.
Monari, Antonio
Miranda, Miguel A.
Hernández-Gil, Javier
Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
author_role author
author2 Monari, Antonio
Miranda, Miguel A.
Hernández-Gil, Javier
Lhiaubet, Virginie Lyria|||0000-0002-8205-8892
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Instituto Universitario Mixto de Tecnología Química
European Commission
Generalitat Valenciana
Ministerio de Universidades
Agencia Estatal de Investigación
European Regional Development Fund
Universitat Politècnica de València
Agence Nationale de la Recherche, Francia
Repositorio Institucional de la Universitat Politècnica de València Riunet
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 [EN] 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
2024-07-08
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://riunet.upv.es/handle/10251/209229
url https://riunet.upv.es/handle/10251/209229
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2021-128348NB-I00 TRANSFERENCIA DE ENERGIA TRIPLETE-TRIPLETE A LARGA DISTANCIA EN SISTEMAS MODELO DE ADN
Agence Nationale de la Recherche, Francia https://doi.org/10.13039/501100001665 ANR-18-IDEX-0001 Université de Paris
Agence Nationale de la Recherche, Francia https://doi.org/10.13039/501100001665 ANR-11-LABX-0086
Agence Nationale de la Recherche, Francia https://doi.org/10.13039/501100001665 ANR-11-IDEX-05-02
Generalitat Valenciana https://doi.org/10.13039/501100003359 CIAICO%2F2021%2F061
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 CEX2021-001230-S
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 PRE 2019-089665
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reconocimiento (by)
http://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reconocimiento (by)
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Frontiers Media SA
publisher.none.fl_str_mv Frontiers Media SA
dc.source.none.fl_str_mv reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
instname:Universitat Politècnica de València (UPV)
instname_str Universitat Politècnica de València (UPV)
reponame_str RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
collection RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812455

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