Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group

Autores
Kolmakov, Kirill; Wurm, Christian; Sednev, Maksim V.; Bossi, Mariano Luis; Belov, Vladimir N.; Hell, Stefan W.
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Caged near-IR emitting fluorescent dyes are in high demand in optical microscopy but up to now were unavailable. We discovered that the combination of a carbopyronine dye core and a photosensitive 2-diazo-1-indanone residue leads to masked near-IR emitting fluorescent dyes. Illumination of these caged dyes with either UV or visible light (λ < 420 nm) efficiently generates fluorescent compounds with absorption and emission at 635 nm and 660 nm, respectively. A high-yielding synthetic route with attractive possibilities for further dye design is described in detail. Good photostability, high contrast, and a large fluorescence quantum yield after uncaging are the most important features of the new compounds for non-invasive imaging in high-resolution optical microscopy. For use in immunolabelling the caged dyes were decorated with a (hydrophilic) linker and an (activated) carboxyl group.
Fil: Kolmakov, Kirill. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Wurm, Christian. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Sednev, Maksim V.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
Materia
Cage Compounds
Superresolution Microscopy
Carbopyronines Carbopyronines
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/70877
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging groupKolmakov, KirillWurm, ChristianSednev, Maksim V.Bossi, Mariano LuisBelov, Vladimir N.Hell, Stefan W.Cage CompoundsSuperresolution MicroscopyCarbopyronines Carbopyronineshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Caged near-IR emitting fluorescent dyes are in high demand in optical microscopy but up to now were unavailable. We discovered that the combination of a carbopyronine dye core and a photosensitive 2-diazo-1-indanone residue leads to masked near-IR emitting fluorescent dyes. Illumination of these caged dyes with either UV or visible light (λ < 420 nm) efficiently generates fluorescent compounds with absorption and emission at 635 nm and 660 nm, respectively. A high-yielding synthetic route with attractive possibilities for further dye design is described in detail. Good photostability, high contrast, and a large fluorescence quantum yield after uncaging are the most important features of the new compounds for non-invasive imaging in high-resolution optical microscopy. For use in immunolabelling the caged dyes were decorated with a (hydrophilic) linker and an (activated) carboxyl group.Fil: Kolmakov, Kirill. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Wurm, Christian. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Sednev, Maksim V.. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Bossi, Mariano Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; AlemaniaRoyal Society of Chemistry2012-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/70877Kolmakov, Kirill; Wurm, Christian; Sednev, Maksim V.; Bossi, Mariano Luis; Belov, Vladimir N.; et al.; Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 11; 3; 3-2012; 522-5321474-905XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2012/pp/c1pp05321c/unauthinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C1PP05321Cinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:12:56Zoai:ri.conicet.gov.ar:11336/70877instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:12:56.884CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
title Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
spellingShingle Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
Kolmakov, Kirill
Cage Compounds
Superresolution Microscopy
Carbopyronines Carbopyronines
title_short Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
title_full Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
title_fullStr Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
title_full_unstemmed Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
title_sort Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group
dc.creator.none.fl_str_mv Kolmakov, Kirill
Wurm, Christian
Sednev, Maksim V.
Bossi, Mariano Luis
Belov, Vladimir N.
Hell, Stefan W.
author Kolmakov, Kirill
author_facet Kolmakov, Kirill
Wurm, Christian
Sednev, Maksim V.
Bossi, Mariano Luis
Belov, Vladimir N.
Hell, Stefan W.
author_role author
author2 Wurm, Christian
Sednev, Maksim V.
Bossi, Mariano Luis
Belov, Vladimir N.
Hell, Stefan W.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Cage Compounds
Superresolution Microscopy
Carbopyronines Carbopyronines
topic Cage Compounds
Superresolution Microscopy
Carbopyronines Carbopyronines
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Caged near-IR emitting fluorescent dyes are in high demand in optical microscopy but up to now were unavailable. We discovered that the combination of a carbopyronine dye core and a photosensitive 2-diazo-1-indanone residue leads to masked near-IR emitting fluorescent dyes. Illumination of these caged dyes with either UV or visible light (λ < 420 nm) efficiently generates fluorescent compounds with absorption and emission at 635 nm and 660 nm, respectively. A high-yielding synthetic route with attractive possibilities for further dye design is described in detail. Good photostability, high contrast, and a large fluorescence quantum yield after uncaging are the most important features of the new compounds for non-invasive imaging in high-resolution optical microscopy. For use in immunolabelling the caged dyes were decorated with a (hydrophilic) linker and an (activated) carboxyl group.
Fil: Kolmakov, Kirill. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Wurm, Christian. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Sednev, Maksim V.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
description Caged near-IR emitting fluorescent dyes are in high demand in optical microscopy but up to now were unavailable. We discovered that the combination of a carbopyronine dye core and a photosensitive 2-diazo-1-indanone residue leads to masked near-IR emitting fluorescent dyes. Illumination of these caged dyes with either UV or visible light (λ < 420 nm) efficiently generates fluorescent compounds with absorption and emission at 635 nm and 660 nm, respectively. A high-yielding synthetic route with attractive possibilities for further dye design is described in detail. Good photostability, high contrast, and a large fluorescence quantum yield after uncaging are the most important features of the new compounds for non-invasive imaging in high-resolution optical microscopy. For use in immunolabelling the caged dyes were decorated with a (hydrophilic) linker and an (activated) carboxyl group.
publishDate 2012
dc.date.none.fl_str_mv 2012-03
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/70877
Kolmakov, Kirill; Wurm, Christian; Sednev, Maksim V.; Bossi, Mariano Luis; Belov, Vladimir N.; et al.; Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 11; 3; 3-2012; 522-532
1474-905X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/70877
identifier_str_mv Kolmakov, Kirill; Wurm, Christian; Sednev, Maksim V.; Bossi, Mariano Luis; Belov, Vladimir N.; et al.; Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 11; 3; 3-2012; 522-532
1474-905X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2012/pp/c1pp05321c/unauth
info:eu-repo/semantics/altIdentifier/doi/10.1039/C1PP05321C
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
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:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.982451

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