Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells

Releasing bioactive molecules in specific subcellular locations from the corresponding caged precursors offers great potential in photopharmacology, especially when using biologically compatible visible light. By taking advantage of the intrinsic preference of COUPY coumarins for mitochondria and th...

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Detalhes bibliográficos
Autores: López Corrales, Marta, Rovira, Anna, Gandioso, Albert, Nonell, Santi, Bosch, Manel, Marchán, Vicente
Formato: artículo
Fecha de publicación:2023
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:20.500.14342/4663
Acesso em linha:http://hdl.handle.net/20.500.14342/4663
https://doi.org/10.1021/acs.joc.3c00387
Access Level:acceso abierto
Palavra-chave:Aromatic compounds
Electromagnetic radiation
Irradiation
Mitochondria
Mixtures
Compostos aromàtics
Electromagnetisme
Irradiació
Mitocondris
Mescles (Química)
537
576
577
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oai_identifier_str oai:recercat.cat:20.500.14342/4663
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spelling Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living CellsLópez Corrales, MartaRovira, AnnaGandioso, AlbertNonell, SantiBosch, ManelMarchán, VicenteAromatic compoundsElectromagnetic radiationIrradiationMitochondriaMixturesCompostos aromàticsElectromagnetismeIrradiacióMitocondrisMescles (Química)537576577Releasing bioactive molecules in specific subcellular locations from the corresponding caged precursors offers great potential in photopharmacology, especially when using biologically compatible visible light. By taking advantage of the intrinsic preference of COUPY coumarins for mitochondria and their long wavelength absorption in the visible region, we have synthesized and fully characterized a series of COUPY-caged model compounds to investigate how the structure of the coumarin caging group affects the rate and efficiency of the photolysis process. Uncaging studies using yellow (560 nm) and red light (620 nm) in phosphate-buffered saline medium have demonstrated that the incorporation of a methyl group in a position adjacent to the photocleavable bond is particularly important to fine-tune the photochemical properties of the caging group. Additionally, the use of a COUPY-caged version of the protonophore 2,4-dinitrophenol allowed us to confirm by confocal microscopy that photoactivation can occur within mitochondria of living HeLa cells upon irradiation with low doses of yellow light. The new photolabile protecting groups presented here complement the photochemical toolbox in therapeutic applications since they will facilitate the delivery of photocages of biologically active compounds into mitochondria.info:eu-repo/semantics/publishedVersionAmerican Chemical SocietyUniversitat Ramon Llull. IQS2023info:eu-repo/semantics/articlep.13http://hdl.handle.net/20.500.14342/4663https://doi.org/10.1021/acs.joc.3c00387reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésThe Journal of Organic Chemistry 2023, 88, 7128-7140info:eu-repo/grantAgreement/MINECO/PN I+D/CTQ2017-84779-Rinfo:eu-repo/grantAgreement/MCI/PN I+D/PID2020-117508RB-I00© L'autor/aAttribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:20.500.14342/46632026-05-29T05:05:01Z
dc.title.none.fl_str_mv Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
title Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
spellingShingle Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
López Corrales, Marta
Aromatic compounds
Electromagnetic radiation
Irradiation
Mitochondria
Mixtures
Compostos aromàtics
Electromagnetisme
Irradiació
Mitocondris
Mescles (Química)
537
576
577
title_short Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
title_full Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
title_fullStr Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
title_full_unstemmed Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
title_sort Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells
dc.creator.none.fl_str_mv López Corrales, Marta
Rovira, Anna
Gandioso, Albert
Nonell, Santi
Bosch, Manel
Marchán, Vicente
author López Corrales, Marta
author_facet López Corrales, Marta
Rovira, Anna
Gandioso, Albert
Nonell, Santi
Bosch, Manel
Marchán, Vicente
author_role author
author2 Rovira, Anna
Gandioso, Albert
Nonell, Santi
Bosch, Manel
Marchán, Vicente
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universitat Ramon Llull. IQS
dc.subject.none.fl_str_mv Aromatic compounds
Electromagnetic radiation
Irradiation
Mitochondria
Mixtures
Compostos aromàtics
Electromagnetisme
Irradiació
Mitocondris
Mescles (Química)
537
576
577
topic Aromatic compounds
Electromagnetic radiation
Irradiation
Mitochondria
Mixtures
Compostos aromàtics
Electromagnetisme
Irradiació
Mitocondris
Mescles (Química)
537
576
577
description Releasing bioactive molecules in specific subcellular locations from the corresponding caged precursors offers great potential in photopharmacology, especially when using biologically compatible visible light. By taking advantage of the intrinsic preference of COUPY coumarins for mitochondria and their long wavelength absorption in the visible region, we have synthesized and fully characterized a series of COUPY-caged model compounds to investigate how the structure of the coumarin caging group affects the rate and efficiency of the photolysis process. Uncaging studies using yellow (560 nm) and red light (620 nm) in phosphate-buffered saline medium have demonstrated that the incorporation of a methyl group in a position adjacent to the photocleavable bond is particularly important to fine-tune the photochemical properties of the caging group. Additionally, the use of a COUPY-caged version of the protonophore 2,4-dinitrophenol allowed us to confirm by confocal microscopy that photoactivation can occur within mitochondria of living HeLa cells upon irradiation with low doses of yellow light. The new photolabile protecting groups presented here complement the photochemical toolbox in therapeutic applications since they will facilitate the delivery of photocages of biologically active compounds into mitochondria.
publishDate 2023
dc.date.none.fl_str_mv 2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/20.500.14342/4663
https://doi.org/10.1021/acs.joc.3c00387
url http://hdl.handle.net/20.500.14342/4663
https://doi.org/10.1021/acs.joc.3c00387
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv The Journal of Organic Chemistry 2023, 88, 7128-7140
info:eu-repo/grantAgreement/MINECO/PN I+D/CTQ2017-84779-R
info:eu-repo/grantAgreement/MCI/PN I+D/PID2020-117508RB-I00
dc.rights.none.fl_str_mv © L'autor/a
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv © L'autor/a
Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv p.13
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869416591886647296
score 15,811543

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