Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths

[EN] Photodynamic therapy (PDT) is an emerging clinical tool that uses light as an agent unleashing cytotoxic activity for treating cancer and other diseases, including those showing drug resistance. One of the main areas of research to fully implement PDT as a real alternative to chemo or radiother...

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Autores: Soler-Beatty, Jennifer, Avellanal-Zaballa, Edurne, Durán-Sampedro, Gonzalo, Agarrabeitia, Antonia R., Bañuelos, Jorge, Ortiz, María J., García-Fernández, Alba|||0000-0002-8416-1674, Martínez-Máñez, Ramón|||0000-0001-5873-9674
Tipo de recurso: artículo
Fecha de publicación:2025
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:10251/230465
Acceso en línea:https://riunet.upv.es/handle/10251/230465
Access Level:acceso abierto
Palabra clave:Photodynamic therapy
Photosensitizers
Reactive oxygen species
BODIPY dimers
Near-infrared activation
Cancer treatment
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spelling Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengthsSoler-Beatty, JenniferAvellanal-Zaballa, EdurneDurán-Sampedro, GonzaloAgarrabeitia, Antonia R.Bañuelos, JorgeOrtiz, María J.García-Fernández, Alba|||0000-0002-8416-1674Martínez-Máñez, Ramón|||0000-0001-5873-9674Photodynamic therapyPhotosensitizersReactive oxygen speciesBODIPY dimersNear-infrared activationCancer treatment[EN] Photodynamic therapy (PDT) is an emerging clinical tool that uses light as an agent unleashing cytotoxic activity for treating cancer and other diseases, including those showing drug resistance. One of the main areas of research to fully implement PDT as a real alternative to chemo or radiotherapy is the development of improved photosensitizers (PSs). This work aims to contribute to the design of novel PSs able to generate reactive oxygen species (ROS) upon activation with light within the biological window (deep red or near-infrared region) while being non-toxic under dark conditions (heavy-atom-free). For this, we have chosen BODIPY-based covalent dimers directly linked through their 3-position as model structures. This molecular scaffold has been previously tested as a fluorescent probe to stain cells, but not as a PS for ROS generation under red illumination. Using readily available synthetic protocols, we have changed the steric hindrance around the linkage and added functional groups suited to enhance targetable biorecognition and solubility in physiological media. The spectroscopic characterization confirms that these dimers are photoactivated in a spectral window approaching 700 nm and display noticeable fluorescence signals beyond this wavelength, together with a notable generation of singlet oxygen. Encouraged by these photophysical signatures, we conducted in vitro trials in cancer cells. These assays ratify the ability of most of the herein reported dimers to sensitize ROS and induce cell death upon long-wavelength illumination.The authors acknowledge grants PID2020-114755GB-C32 and -C33, and PID2021-128141OB-C22 funded by the Spanish MCIN/AEI/10.13039/501100011033, and grant IT1639-22 funded by the Basque Government.Royal Society of ChemistryDepartamento de QuímicaEscuela Técnica Superior de Ingeniería IndustrialInstituto Interuniversitario de Investigación de Reconocimiento Molecular y Desarrollo TecnológicoEusko JaurlaritzaAgencia Estatal de InvestigaciónRepositorio Institucional de la Universitat Politècnica de València Riunet20252025-01-20journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://riunet.upv.es/handle/10251/230465reponame: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 2017-2020 PID2020-114755GB-C32 INGENERIA SINTETICA DE SONDAS MOLECULARES CON MULTIPLES FUNCIONES FOTONICAS PARA APLICACIONES BIOMEDICAS AVANZADASAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2020-114755GB-C33 SIMULACION COMPUTACIONAL Y CARACTERIZACION FOTOFISICA AVANZADA DE BIOSONDAS MOLECULARES INTELIGENTESAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2021-128141OB-C22 DESARROLLO DE NUEVOS MATERIALES INTELIGENTES Y SU APLICACION COMO SISTEMAS ANTIVIRALES, ANTIBIOFILM, ANTIENZIMATICOS Y ANTIMICROBIANOS PARA LA INDUSTRIA ALIMENTARIA.Eusko Jaurlaritza Eusko Jaurlaritza IT1639-22open accesshttp://purl.org/coar/access_right/c_abf2Reconocimiento (by)http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:riunet.upv.es:10251/2304652026-06-13T07:49:27Z
dc.title.none.fl_str_mv Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
title Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
spellingShingle Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
Soler-Beatty, Jennifer
Photodynamic therapy
Photosensitizers
Reactive oxygen species
BODIPY dimers
Near-infrared activation
Cancer treatment
title_short Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
title_full Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
title_fullStr Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
title_full_unstemmed Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
title_sort Heavy-atom-free BODIPY-based photodynamic therapy agents activated at long wavelengths
dc.creator.none.fl_str_mv Soler-Beatty, Jennifer
Avellanal-Zaballa, Edurne
Durán-Sampedro, Gonzalo
Agarrabeitia, Antonia R.
Bañuelos, Jorge
Ortiz, María J.
García-Fernández, Alba|||0000-0002-8416-1674
Martínez-Máñez, Ramón|||0000-0001-5873-9674
author Soler-Beatty, Jennifer
author_facet Soler-Beatty, Jennifer
Avellanal-Zaballa, Edurne
Durán-Sampedro, Gonzalo
Agarrabeitia, Antonia R.
Bañuelos, Jorge
Ortiz, María J.
García-Fernández, Alba|||0000-0002-8416-1674
Martínez-Máñez, Ramón|||0000-0001-5873-9674
author_role author
author2 Avellanal-Zaballa, Edurne
Durán-Sampedro, Gonzalo
Agarrabeitia, Antonia R.
Bañuelos, Jorge
Ortiz, María J.
García-Fernández, Alba|||0000-0002-8416-1674
Martínez-Máñez, Ramón|||0000-0001-5873-9674
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química
Escuela Técnica Superior de Ingeniería Industrial
Instituto Interuniversitario de Investigación de Reconocimiento Molecular y Desarrollo Tecnológico
Eusko Jaurlaritza
Agencia Estatal de Investigación
Repositorio Institucional de la Universitat Politècnica de València Riunet
dc.subject.none.fl_str_mv Photodynamic therapy
Photosensitizers
Reactive oxygen species
BODIPY dimers
Near-infrared activation
Cancer treatment
topic Photodynamic therapy
Photosensitizers
Reactive oxygen species
BODIPY dimers
Near-infrared activation
Cancer treatment
description [EN] Photodynamic therapy (PDT) is an emerging clinical tool that uses light as an agent unleashing cytotoxic activity for treating cancer and other diseases, including those showing drug resistance. One of the main areas of research to fully implement PDT as a real alternative to chemo or radiotherapy is the development of improved photosensitizers (PSs). This work aims to contribute to the design of novel PSs able to generate reactive oxygen species (ROS) upon activation with light within the biological window (deep red or near-infrared region) while being non-toxic under dark conditions (heavy-atom-free). For this, we have chosen BODIPY-based covalent dimers directly linked through their 3-position as model structures. This molecular scaffold has been previously tested as a fluorescent probe to stain cells, but not as a PS for ROS generation under red illumination. Using readily available synthetic protocols, we have changed the steric hindrance around the linkage and added functional groups suited to enhance targetable biorecognition and solubility in physiological media. The spectroscopic characterization confirms that these dimers are photoactivated in a spectral window approaching 700 nm and display noticeable fluorescence signals beyond this wavelength, together with a notable generation of singlet oxygen. Encouraged by these photophysical signatures, we conducted in vitro trials in cancer cells. These assays ratify the ability of most of the herein reported dimers to sensitize ROS and induce cell death upon long-wavelength illumination.
publishDate 2025
dc.date.none.fl_str_mv 2025
2025-01-20
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/10251/230465
url https://riunet.upv.es/handle/10251/230465
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 2017-2020 PID2020-114755GB-C32 INGENERIA SINTETICA DE SONDAS MOLECULARES CON MULTIPLES FUNCIONES FOTONICAS PARA APLICACIONES BIOMEDICAS AVANZADAS
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2020-114755GB-C33 SIMULACION COMPUTACIONAL Y CARACTERIZACION FOTOFISICA AVANZADA DE BIOSONDAS MOLECULARES INTELIGENTES
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2021-128141OB-C22 DESARROLLO DE NUEVOS MATERIALES INTELIGENTES Y SU APLICACION COMO SISTEMAS ANTIVIRALES, ANTIBIOFILM, ANTIENZIMATICOS Y ANTIMICROBIANOS PARA LA INDUSTRIA ALIMENTARIA.
Eusko Jaurlaritza Eusko Jaurlaritza IT1639-22
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 15.81155

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