Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers

Heavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), r...

Descripción completa

Detalles Bibliográficos
Autores: Díaz Norambuena, Carolina, Avellanal Zaballa, Edurne, Prieto Castañeda, Alejandro, Bañuelos Prieto, Jorge, de la Moya, Santiago, Rodríguez Agarrabeitia, Antonia, Ortiz García, María Josefa
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/62076
Acceso en línea:http://hdl.handle.net/10810/62076
Access Level:acceso abierto
Palabra clave:BODIPY dimers
fluorescence
PDT
photosensitizers
singlet oxygen
id ES_fdb14eebf7510eecfc1e48ec9e13d93a
oai_identifier_str oai:addi.ehu.eus:10810/62076
network_acronym_str ES
network_name_str España
repository_id_str
spelling Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene DimersDíaz Norambuena, CarolinaAvellanal Zaballa, EdurnePrieto Castañeda, AlejandroBañuelos Prieto, Jorgede la Moya, SantiagoRodríguez Agarrabeitia, AntoniaOrtiz García, María JosefaBODIPY dimersfluorescencePDTphotosensitizerssinglet oxygenHeavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), respectively, with minimal side effects. In this regard, BODIPY-based orthogonal dimers have irrupted as suitable candidates for this aim. Herein, we analyse the photophysical properties of a set of formyl-functionalized BODIPY dimers to ascertain their suitability as fluorescent photosensitizers. The conducted computationally aided spectroscopic study determined that the fluorescence/singlet oxygen generation dual performance of these valuable BODIPY dimers not only depends on the BODIPY-BODIPY linkage and the steric hindrance around it, but also can be modulated by proper formyl functionalization at specific chromophoric positions. Thus, we propose regioselective formylation as an effective tool to modulate such a delicate photonic balance in BODIPY-based dimeric photosensitizers. The taming of the excited-state dynamics, in particular intramolecular charge transfer as the key underlying process mediating fluorescence deactivation vs. intersystem crossing increasing, could serve to increase fluorescence for brighter bioimaging, enhance the generation of singlet oxygen for killing activity, or balance both for photo-theragnosis.This research received financial support from the Spanish Ministerio de Ciencia e Innovación (MCIN)/Agencia Estatal de Investigación (AEI) Grants: PID2020-114755GB-C32 and -C33 funded by MCIN/AEI/10.13039/501100011033. Gobierno Vasco (IT1639-22) is also grateful for the financial support.MDPI2023202320232023info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/62076reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MICINN/PID2020-114755GB-C32/info:eu-repo/grantAgreement/MICINN/PID2020-114755GB-C33/https://www.mdpi.com/1422-0067/24/14/11837info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/ 4.0/).oai:addi.ehu.eus:10810/620762026-06-18T09:23:17Z
dc.title.none.fl_str_mv Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
title Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
spellingShingle Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
Díaz Norambuena, Carolina
BODIPY dimers
fluorescence
PDT
photosensitizers
singlet oxygen
title_short Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
title_full Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
title_fullStr Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
title_full_unstemmed Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
title_sort Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers
dc.creator.none.fl_str_mv Díaz Norambuena, Carolina
Avellanal Zaballa, Edurne
Prieto Castañeda, Alejandro
Bañuelos Prieto, Jorge
de la Moya, Santiago
Rodríguez Agarrabeitia, Antonia
Ortiz García, María Josefa
author Díaz Norambuena, Carolina
author_facet Díaz Norambuena, Carolina
Avellanal Zaballa, Edurne
Prieto Castañeda, Alejandro
Bañuelos Prieto, Jorge
de la Moya, Santiago
Rodríguez Agarrabeitia, Antonia
Ortiz García, María Josefa
author_role author
author2 Avellanal Zaballa, Edurne
Prieto Castañeda, Alejandro
Bañuelos Prieto, Jorge
de la Moya, Santiago
Rodríguez Agarrabeitia, Antonia
Ortiz García, María Josefa
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv BODIPY dimers
fluorescence
PDT
photosensitizers
singlet oxygen
topic BODIPY dimers
fluorescence
PDT
photosensitizers
singlet oxygen
description Heavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), respectively, with minimal side effects. In this regard, BODIPY-based orthogonal dimers have irrupted as suitable candidates for this aim. Herein, we analyse the photophysical properties of a set of formyl-functionalized BODIPY dimers to ascertain their suitability as fluorescent photosensitizers. The conducted computationally aided spectroscopic study determined that the fluorescence/singlet oxygen generation dual performance of these valuable BODIPY dimers not only depends on the BODIPY-BODIPY linkage and the steric hindrance around it, but also can be modulated by proper formyl functionalization at specific chromophoric positions. Thus, we propose regioselective formylation as an effective tool to modulate such a delicate photonic balance in BODIPY-based dimeric photosensitizers. The taming of the excited-state dynamics, in particular intramolecular charge transfer as the key underlying process mediating fluorescence deactivation vs. intersystem crossing increasing, could serve to increase fluorescence for brighter bioimaging, enhance the generation of singlet oxygen for killing activity, or balance both for photo-theragnosis.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/62076
url http://hdl.handle.net/10810/62076
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MICINN/PID2020-114755GB-C32/
info:eu-repo/grantAgreement/MICINN/PID2020-114755GB-C33/
https://www.mdpi.com/1422-0067/24/14/11837
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869425589730934784
score 15,300724

Similares en LA Referencia