Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques

This study presents the synthesis and characterization of two fluorescent norbornadiene (NBD) photoswitches, each incorporating two conjugated pyrene units. Expanding on the limited repertoire of reported photoswitchable fluorescent NBDs, we explore their properties with a focus on applications in b...

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Autores: Ghasemi, Shima, Shamsabadi, Shima, Olesund, Axel, Najera Albendin, Francisco, Hillers Bendtsen, Andreas Erbs, Edhborg, Fredrik, Aslam, Adil S., Larsson, Wera, Wang, Zhihang, Amombo Noa, Francoise Mystere, Salthouse, Rebeca Jane|||0000-0003-2213-6956, Öhrström, Lars, Hölzel, Helen, Pérez Inestrosa, Ezequiel
Formato: artículo
Fecha de publicación:2024
País:España
Recursos:Universitat Politècnica de Catalunya (UPC)
Repositorio:UPCommons. Portal del coneixement obert de la UPC
Idioma:inglés
OAI Identifier:oai:upcommons.upc.edu:2117/414055
Acesso em linha:https://hdl.handle.net/2117/414055
https://dx.doi.org/10.1002/chem.202400322
Access Level:acceso abierto
Palavra-chave:Chemical engineering
Enginyeria química
Àrees temàtiques de la UPC::Enginyeria química
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spelling Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaquesGhasemi, ShimaShamsabadi, ShimaOlesund, AxelNajera Albendin, FranciscoHillers Bendtsen, Andreas ErbsEdhborg, FredrikAslam, Adil S.Larsson, WeraWang, ZhihangAmombo Noa, Francoise MystereSalthouse, Rebeca Jane|||0000-0003-2213-6956Öhrström, LarsHölzel, HelenPérez Inestrosa, EzequielChemical engineeringEnginyeria químicaÀrees temàtiques de la UPC::Enginyeria químicaThis study presents the synthesis and characterization of two fluorescent norbornadiene (NBD) photoswitches, each incorporating two conjugated pyrene units. Expanding on the limited repertoire of reported photoswitchable fluorescent NBDs, we explore their properties with a focus on applications in bioimaging of amyloid beta (Aß) plaques. While the fluorescence emission of the NBD decreases upon photoisomerization, aligning with what has been previously reported, for the first time we observed luminescence after irradiation of the quadricyclane (QC) isomer. We deduce how the observed emission is induced by photoisomerization to the excited state of the parent isomer (NBD) which is then the emitting species. Thorough characterizations including NMR, UV-Vis, fluorescence, X-ray structural analysis and density functional theory (DFT) calculations provide a comprehensive understanding of these systems. Notably, one NBD-QC system exhibits exceptional durability. Additionally, these molecules serve as effective fluorescent stains targeting Aß plaques in situ, with observed NBD/QC switching within the plaques. Molecular docking simulations explore NBD interactions with amyloid, unveiling novel binding modes. These insights mark a crucial advancement in the comprehension and design of future photochromic NBDs for bioimaging applications and beyond, emphasizing their potential in studying and addressing protein aggregates.Peer Reviewed20242024-01-0120242024-09-10journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/414055https://dx.doi.org/10.1002/chem.202400322reponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/4140552026-05-27T15:37:01Z
dc.title.none.fl_str_mv Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
title Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
spellingShingle Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
Ghasemi, Shima
Chemical engineering
Enginyeria química
Àrees temàtiques de la UPC::Enginyeria química
title_short Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
title_full Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
title_fullStr Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
title_full_unstemmed Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
title_sort Pyrene functionalized norbornadiene-quadricyclane fluorescent photoswitches: characterization of their spectral properties and application in imaging of amyloid beta plaques
dc.creator.none.fl_str_mv Ghasemi, Shima
Shamsabadi, Shima
Olesund, Axel
Najera Albendin, Francisco
Hillers Bendtsen, Andreas Erbs
Edhborg, Fredrik
Aslam, Adil S.
Larsson, Wera
Wang, Zhihang
Amombo Noa, Francoise Mystere
Salthouse, Rebeca Jane|||0000-0003-2213-6956
Öhrström, Lars
Hölzel, Helen
Pérez Inestrosa, Ezequiel
author Ghasemi, Shima
author_facet Ghasemi, Shima
Shamsabadi, Shima
Olesund, Axel
Najera Albendin, Francisco
Hillers Bendtsen, Andreas Erbs
Edhborg, Fredrik
Aslam, Adil S.
Larsson, Wera
Wang, Zhihang
Amombo Noa, Francoise Mystere
Salthouse, Rebeca Jane|||0000-0003-2213-6956
Öhrström, Lars
Hölzel, Helen
Pérez Inestrosa, Ezequiel
author_role author
author2 Shamsabadi, Shima
Olesund, Axel
Najera Albendin, Francisco
Hillers Bendtsen, Andreas Erbs
Edhborg, Fredrik
Aslam, Adil S.
Larsson, Wera
Wang, Zhihang
Amombo Noa, Francoise Mystere
Salthouse, Rebeca Jane|||0000-0003-2213-6956
Öhrström, Lars
Hölzel, Helen
Pérez Inestrosa, Ezequiel
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Chemical engineering
Enginyeria química
Àrees temàtiques de la UPC::Enginyeria química
topic Chemical engineering
Enginyeria química
Àrees temàtiques de la UPC::Enginyeria química
description This study presents the synthesis and characterization of two fluorescent norbornadiene (NBD) photoswitches, each incorporating two conjugated pyrene units. Expanding on the limited repertoire of reported photoswitchable fluorescent NBDs, we explore their properties with a focus on applications in bioimaging of amyloid beta (Aß) plaques. While the fluorescence emission of the NBD decreases upon photoisomerization, aligning with what has been previously reported, for the first time we observed luminescence after irradiation of the quadricyclane (QC) isomer. We deduce how the observed emission is induced by photoisomerization to the excited state of the parent isomer (NBD) which is then the emitting species. Thorough characterizations including NMR, UV-Vis, fluorescence, X-ray structural analysis and density functional theory (DFT) calculations provide a comprehensive understanding of these systems. Notably, one NBD-QC system exhibits exceptional durability. Additionally, these molecules serve as effective fluorescent stains targeting Aß plaques in situ, with observed NBD/QC switching within the plaques. Molecular docking simulations explore NBD interactions with amyloid, unveiling novel binding modes. These insights mark a crucial advancement in the comprehension and design of future photochromic NBDs for bioimaging applications and beyond, emphasizing their potential in studying and addressing protein aggregates.
publishDate 2024
dc.date.none.fl_str_mv 2024
2024-01-01
2024
2024-09-10
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://hdl.handle.net/2117/414055
https://dx.doi.org/10.1002/chem.202400322
url https://hdl.handle.net/2117/414055
https://dx.doi.org/10.1002/chem.202400322
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution 4.0 International
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
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:UPCommons. Portal del coneixement obert de la UPC
instname:Universitat Politècnica de Catalunya (UPC)
instname_str Universitat Politècnica de Catalunya (UPC)
reponame_str UPCommons. Portal del coneixement obert de la UPC
collection UPCommons. Portal del coneixement obert de la UPC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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