Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups

Although photolabile protecting groups (PPGs) have found widespread applications in several fields of chemistry, biology and materials science, there is a growing interest in expanding the photochemical toolbox to overcome some of the limitations of classical caging groups. In this work, the synthes...

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Authors: López-Corrales, Marta, Rovira, Anna, Gandioso, Albert, Bosch Marimon, Manel, Nonell, Santi, Marchán Sancho, Vicente
Format: article
Status:Versión aceptada para publicación
Publication Date:2020
Country:España
Institution:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repository:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/172162
Online Access:https://hdl.handle.net/2445/172162
Access Level:Open access
Keyword:Cumarines
Mitocondris
Coumarins
Mitochondria
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spelling Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groupsLópez-Corrales, MartaRovira, AnnaGandioso, AlbertBosch Marimon, ManelNonell, SantiMarchán Sancho, VicenteCumarinesMitocondrisCoumarinsMitochondriaAlthough photolabile protecting groups (PPGs) have found widespread applications in several fields of chemistry, biology and materials science, there is a growing interest in expanding the photochemical toolbox to overcome some of the limitations of classical caging groups. In this work, the synthesis of a new class of visible-light-sensitive PPGs based on low-molecular weight COUPY fluorophores with several attractive properties, including long-wavelength absorption, is reported. Besides being stable to spontaneous hydrolysis in the dark, COUPY-based PPGs can be efficiently photoactivated with yellow (560 nm) and red light (620 nm) under physicological-like conditions, thereby offering the possibility of unmasking functional groups from COUPY photocages under irradiation conditions in which other PPGs remain stable. Additionally, COUPY photocages exhibit excellent cellular uptake and accumulate selectively in mitochondria, opening the door to delivering caged analogues of biologically active compounds into this organelleWiley-VCH2020202120202020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion7 p.application/pdfapplication/pdfhttps://hdl.handle.net/2445/172162Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: https://doi.org/10.1002/chem.202002314Chemistry-A European Journal, 2020, vol. 26https://doi.org/10.1002/chem.202002314(c) Wiley-VCH, 2020info:eu-repo/semantics/openAccessoai:recercat.cat:2445/1721622026-05-29T05:05:01Z
dc.title.none.fl_str_mv Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
title Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
spellingShingle Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
López-Corrales, Marta
Cumarines
Mitocondris
Coumarins
Mitochondria
title_short Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
title_full Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
title_fullStr Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
title_full_unstemmed Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
title_sort Transformation of COUPY fluorophores into a novel class of visible light-cleavable photolabile protecting groups
dc.creator.none.fl_str_mv López-Corrales, Marta
Rovira, Anna
Gandioso, Albert
Bosch Marimon, Manel
Nonell, Santi
Marchán Sancho, Vicente
author López-Corrales, Marta
author_facet López-Corrales, Marta
Rovira, Anna
Gandioso, Albert
Bosch Marimon, Manel
Nonell, Santi
Marchán Sancho, Vicente
author_role author
author2 Rovira, Anna
Gandioso, Albert
Bosch Marimon, Manel
Nonell, Santi
Marchán Sancho, Vicente
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Cumarines
Mitocondris
Coumarins
Mitochondria
topic Cumarines
Mitocondris
Coumarins
Mitochondria
description Although photolabile protecting groups (PPGs) have found widespread applications in several fields of chemistry, biology and materials science, there is a growing interest in expanding the photochemical toolbox to overcome some of the limitations of classical caging groups. In this work, the synthesis of a new class of visible-light-sensitive PPGs based on low-molecular weight COUPY fluorophores with several attractive properties, including long-wavelength absorption, is reported. Besides being stable to spontaneous hydrolysis in the dark, COUPY-based PPGs can be efficiently photoactivated with yellow (560 nm) and red light (620 nm) under physicological-like conditions, thereby offering the possibility of unmasking functional groups from COUPY photocages under irradiation conditions in which other PPGs remain stable. Additionally, COUPY photocages exhibit excellent cellular uptake and accumulate selectively in mitochondria, opening the door to delivering caged analogues of biologically active compounds into this organelle
publishDate 2020
dc.date.none.fl_str_mv 2020
2020
2020
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/172162
url https://hdl.handle.net/2445/172162
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1002/chem.202002314
Chemistry-A European Journal, 2020, vol. 26
https://doi.org/10.1002/chem.202002314
dc.rights.none.fl_str_mv (c) Wiley-VCH, 2020
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley-VCH, 2020
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 7 p.
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
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
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score 15.811543

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