AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents

Biscyclometalated Ir(III) complexes involving BODIPYbased ancillary ligands, where the BODIPY unit is grafted to different chelating cores (acetylacetonate for Ir-1 and Ir-2, and bipyridine for Ir-3) by the BODIPY meso position, have been synthesized and characterized. Complexes having the BODIPY mo...

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Autores: Palao, Eduardo, Sola Llano, Rebeca, Tabero, Andrea, Manzano Moro, Hegoi, Agarrabeitia, Antonia R., Villanueva, Angeles, López Arbeloa, Iñigo María, Martínez Martínez, Virginia, Ortiz, María J.
Tipo de recurso: artículo
Fecha de publicación:2017
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/65165
Acceso en línea:http://hdl.handle.net/10810/65165
Access Level:acceso abierto
Palabra clave:Iridium(III) complex
BODIPYs
singlet oxygen
fluorescent-photosensitizers
photodynamic therapy
HeLa cells
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spelling AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agentsPalao, EduardoSola Llano, RebecaTabero, AndreaManzano Moro, HegoiAgarrabeitia, Antonia R.Villanueva, AngelesLópez Arbeloa, Iñigo MaríaMartínez Martínez, VirginiaOrtiz, María J.Iridium(III) complexBODIPYssinglet oxygenfluorescent-photosensitizersphotodynamic therapyHeLa cellsBiscyclometalated Ir(III) complexes involving BODIPYbased ancillary ligands, where the BODIPY unit is grafted to different chelating cores (acetylacetonate for Ir-1 and Ir-2, and bipyridine for Ir-3) by the BODIPY meso position, have been synthesized and characterized. Complexes having the BODIPY moiety directly grafted to acetylacetonate (Ir-1 and Ir-2) exhibit higher absorption coefficient (ca. ε = 4.46 104 M-1 cm-1 and 3.38 104 M-1cm-1 at 517 nm and 594 nm, respectively), higher moderate-fluorescence emission (ca. fl = 0.08 and 0.22 at 528 nm and 652 nm, respectively) and, especially, more efficient singlet oxygen generation upon visible-light irradiation (ca.  = 0.86 and 0.59, respectively) than that exhibited by Ir-3 (ca.  = 0.51, but only under UV light). Phosphorescence emission, nanosecond time-resolved transient absorption and DFT calculations suggest that BODIPY-localized long-lived 3IL states are populated for Ir-1 and Ir-2. In-vitro photodynamic therapy (PDT) activity studied for Ir-1 and Ir-2 in HeLa cells shows that such complexes are efficiently internalized into the cells, exhibiting low dark- and high photo-cytoxicity, even at significant low complex concentration, making them potentially suitable as theranostic agents.Financial support from MINECO (MAT2014-51937-C-2-P and 3-P and MAT2015-68837-REDT), MICINN (CTQ2013-48767-C3-3-R), Comunidad de Madrid (S2013/MIT-2850) of Spain and Gobierno Vasco (IT912-16) is gratefully acknowledged. V. M-M. thanks MINECO for a postdoctoral contract (RYC-2011-09505). R.S-L thanks UPV-EHU for a postdoctoral fellowship, and A.T. thanks UAM for a predoctoral contract. The authors thank for technical and human support provided by SGIker of UPV/EHU and European funding (ERDF and ESF).Wiley-VCH GmbH, Weinheim202420242017info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/65165reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MICINN/TQ2013-48767-C3-3-R/info:eu-repo/grantAgreement/MINECO/MAT2014-51937-C-2-P/info:eu-repo/grantAgreement/MINECO/MAT2014-51937-C-3-P/info:eu-repo/grantAgreement/MINECO/MAT2015-68837-REDT/info:eu-repo/grantAgreement/MINECO/RYC-2011-09505/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.201701347info:eu-repo/semantics/openAccess© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheimoai:addi.ehu.eus:10810/651652026-06-18T09:23:17Z
dc.title.none.fl_str_mv AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
title AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
spellingShingle AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
Palao, Eduardo
Iridium(III) complex
BODIPYs
singlet oxygen
fluorescent-photosensitizers
photodynamic therapy
HeLa cells
title_short AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
title_full AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
title_fullStr AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
title_full_unstemmed AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
title_sort AcetylacetonateBODIPY−biscyclometalated Iridium(III) complexes: effective strategy towards smarte fluorescentphotosensitizer agents
dc.creator.none.fl_str_mv Palao, Eduardo
Sola Llano, Rebeca
Tabero, Andrea
Manzano Moro, Hegoi
Agarrabeitia, Antonia R.
Villanueva, Angeles
López Arbeloa, Iñigo María
Martínez Martínez, Virginia
Ortiz, María J.
author Palao, Eduardo
author_facet Palao, Eduardo
Sola Llano, Rebeca
Tabero, Andrea
Manzano Moro, Hegoi
Agarrabeitia, Antonia R.
Villanueva, Angeles
López Arbeloa, Iñigo María
Martínez Martínez, Virginia
Ortiz, María J.
author_role author
author2 Sola Llano, Rebeca
Tabero, Andrea
Manzano Moro, Hegoi
Agarrabeitia, Antonia R.
Villanueva, Angeles
López Arbeloa, Iñigo María
Martínez Martínez, Virginia
Ortiz, María J.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Iridium(III) complex
BODIPYs
singlet oxygen
fluorescent-photosensitizers
photodynamic therapy
HeLa cells
topic Iridium(III) complex
BODIPYs
singlet oxygen
fluorescent-photosensitizers
photodynamic therapy
HeLa cells
description Biscyclometalated Ir(III) complexes involving BODIPYbased ancillary ligands, where the BODIPY unit is grafted to different chelating cores (acetylacetonate for Ir-1 and Ir-2, and bipyridine for Ir-3) by the BODIPY meso position, have been synthesized and characterized. Complexes having the BODIPY moiety directly grafted to acetylacetonate (Ir-1 and Ir-2) exhibit higher absorption coefficient (ca. ε = 4.46 104 M-1 cm-1 and 3.38 104 M-1cm-1 at 517 nm and 594 nm, respectively), higher moderate-fluorescence emission (ca. fl = 0.08 and 0.22 at 528 nm and 652 nm, respectively) and, especially, more efficient singlet oxygen generation upon visible-light irradiation (ca.  = 0.86 and 0.59, respectively) than that exhibited by Ir-3 (ca.  = 0.51, but only under UV light). Phosphorescence emission, nanosecond time-resolved transient absorption and DFT calculations suggest that BODIPY-localized long-lived 3IL states are populated for Ir-1 and Ir-2. In-vitro photodynamic therapy (PDT) activity studied for Ir-1 and Ir-2 in HeLa cells shows that such complexes are efficiently internalized into the cells, exhibiting low dark- and high photo-cytoxicity, even at significant low complex concentration, making them potentially suitable as theranostic agents.
publishDate 2017
dc.date.none.fl_str_mv 2017
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/65165
url http://hdl.handle.net/10810/65165
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MICINN/TQ2013-48767-C3-3-R/
info:eu-repo/grantAgreement/MINECO/MAT2014-51937-C-2-P/
info:eu-repo/grantAgreement/MINECO/MAT2014-51937-C-3-P/
info:eu-repo/grantAgreement/MINECO/MAT2015-68837-REDT/
info:eu-repo/grantAgreement/MINECO/RYC-2011-09505/
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.201701347
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
eu_rights_str_mv openAccess
rights_invalid_str_mv © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH GmbH, Weinheim
publisher.none.fl_str_mv Wiley-VCH GmbH, Weinheim
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
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score 15,301603

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