Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy

Autores
Belov, Vladimir N.; Bossi, Mariano Luis; Fölling, Jonas; Boyarskiy, Vadim P.; Hell, Stefan W.
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The design, synthesis, and evaluation of new rhodamine spiroamides are described. These molecules have applications in optical nanoscopy based on random switching of the fluorescent single molecules. The new markers may be used in (co)localization studies of various objects and their (mutual) positions and shape can be determined with a precision of a few tens of nanometers. Multicolor staining, good photoactivation, a large number of emitted photons, and selective chemical binding with amino or thiol groups were achieved due to the presence of various functional groups on the rhodamine spiroamides. Rigidized sulfonated xanthene fragment fused with six-membered rings, N,N′-bis(2,2,2-trifluoroethyl) groups, and a combination of additional double bonds and sulfonic acid groups with simple aliphatic spiroamide residue provide multicolor properties and improve performance of the rhodamine spiroamides in photoactivation and bioconjugation reactions. Having both essential parts of the photoswitchable assembly - the switching and the fluorescent (reporter) groups - combined in one chemical entity make this approach attractive for further development. A series of rhodamine spiroamides is presented along with characterizations of their most relevant properties for application as fluorescent probes in single-molecule switching and localization microscopy. Optical images with resolutions on the nanometer scale illustrate the potential of the labels in the colocalization of biological objects and the two-photon activation technique with optical sectioning.
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Max Planck Institute for Biophysical Chemistry; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Fölling, Jonas. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Boyarskiy, Vadim P.. Max Planck Institute for Biophysical Chemistry; Alemania. St. Petersburg State University; Rusia
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
Materia
Cage Compounds
Dyes/Pigments
Fluorescence
Molecular Switches
Rhodamines
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:11336/73441
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/73441
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopyBelov, Vladimir N.Bossi, Mariano LuisFölling, JonasBoyarskiy, Vadim P.Hell, Stefan W.Cage CompoundsDyes/PigmentsFluorescenceMolecular SwitchesRhodamineshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The design, synthesis, and evaluation of new rhodamine spiroamides are described. These molecules have applications in optical nanoscopy based on random switching of the fluorescent single molecules. The new markers may be used in (co)localization studies of various objects and their (mutual) positions and shape can be determined with a precision of a few tens of nanometers. Multicolor staining, good photoactivation, a large number of emitted photons, and selective chemical binding with amino or thiol groups were achieved due to the presence of various functional groups on the rhodamine spiroamides. Rigidized sulfonated xanthene fragment fused with six-membered rings, N,N′-bis(2,2,2-trifluoroethyl) groups, and a combination of additional double bonds and sulfonic acid groups with simple aliphatic spiroamide residue provide multicolor properties and improve performance of the rhodamine spiroamides in photoactivation and bioconjugation reactions. Having both essential parts of the photoswitchable assembly - the switching and the fluorescent (reporter) groups - combined in one chemical entity make this approach attractive for further development. A series of rhodamine spiroamides is presented along with characterizations of their most relevant properties for application as fluorescent probes in single-molecule switching and localization microscopy. Optical images with resolutions on the nanometer scale illustrate the potential of the labels in the colocalization of biological objects and the two-photon activation technique with optical sectioning.Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Bossi, Mariano Luis. Max Planck Institute for Biophysical Chemistry; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Fölling, Jonas. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Boyarskiy, Vadim P.. Max Planck Institute for Biophysical Chemistry; Alemania. St. Petersburg State University; RusiaFil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; AlemaniaWiley VCH Verlag2009-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/73441Belov, Vladimir N.; Bossi, Mariano Luis; Fölling, Jonas; Boyarskiy, Vadim P.; Hell, Stefan W.; Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy; Wiley VCH Verlag; Chemistry- A European Journal; 15; 41; 10-2009; 10762-107760947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200901333info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200901333info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:41:29Zoai:ri.conicet.gov.ar:11336/73441instacron: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:34982025-09-29 10:41:29.469CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
title Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
spellingShingle Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
Belov, Vladimir N.
Cage Compounds
Dyes/Pigments
Fluorescence
Molecular Switches
Rhodamines
title_short Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
title_full Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
title_fullStr Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
title_full_unstemmed Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
title_sort Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy
dc.creator.none.fl_str_mv Belov, Vladimir N.
Bossi, Mariano Luis
Fölling, Jonas
Boyarskiy, Vadim P.
Hell, Stefan W.
author Belov, Vladimir N.
author_facet Belov, Vladimir N.
Bossi, Mariano Luis
Fölling, Jonas
Boyarskiy, Vadim P.
Hell, Stefan W.
author_role author
author2 Bossi, Mariano Luis
Fölling, Jonas
Boyarskiy, Vadim P.
Hell, Stefan W.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Cage Compounds
Dyes/Pigments
Fluorescence
Molecular Switches
Rhodamines
topic Cage Compounds
Dyes/Pigments
Fluorescence
Molecular Switches
Rhodamines
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The design, synthesis, and evaluation of new rhodamine spiroamides are described. These molecules have applications in optical nanoscopy based on random switching of the fluorescent single molecules. The new markers may be used in (co)localization studies of various objects and their (mutual) positions and shape can be determined with a precision of a few tens of nanometers. Multicolor staining, good photoactivation, a large number of emitted photons, and selective chemical binding with amino or thiol groups were achieved due to the presence of various functional groups on the rhodamine spiroamides. Rigidized sulfonated xanthene fragment fused with six-membered rings, N,N′-bis(2,2,2-trifluoroethyl) groups, and a combination of additional double bonds and sulfonic acid groups with simple aliphatic spiroamide residue provide multicolor properties and improve performance of the rhodamine spiroamides in photoactivation and bioconjugation reactions. Having both essential parts of the photoswitchable assembly - the switching and the fluorescent (reporter) groups - combined in one chemical entity make this approach attractive for further development. A series of rhodamine spiroamides is presented along with characterizations of their most relevant properties for application as fluorescent probes in single-molecule switching and localization microscopy. Optical images with resolutions on the nanometer scale illustrate the potential of the labels in the colocalization of biological objects and the two-photon activation technique with optical sectioning.
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Max Planck Institute for Biophysical Chemistry; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Fölling, Jonas. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Boyarskiy, Vadim P.. Max Planck Institute for Biophysical Chemistry; Alemania. St. Petersburg State University; Rusia
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
description The design, synthesis, and evaluation of new rhodamine spiroamides are described. These molecules have applications in optical nanoscopy based on random switching of the fluorescent single molecules. The new markers may be used in (co)localization studies of various objects and their (mutual) positions and shape can be determined with a precision of a few tens of nanometers. Multicolor staining, good photoactivation, a large number of emitted photons, and selective chemical binding with amino or thiol groups were achieved due to the presence of various functional groups on the rhodamine spiroamides. Rigidized sulfonated xanthene fragment fused with six-membered rings, N,N′-bis(2,2,2-trifluoroethyl) groups, and a combination of additional double bonds and sulfonic acid groups with simple aliphatic spiroamide residue provide multicolor properties and improve performance of the rhodamine spiroamides in photoactivation and bioconjugation reactions. Having both essential parts of the photoswitchable assembly - the switching and the fluorescent (reporter) groups - combined in one chemical entity make this approach attractive for further development. A series of rhodamine spiroamides is presented along with characterizations of their most relevant properties for application as fluorescent probes in single-molecule switching and localization microscopy. Optical images with resolutions on the nanometer scale illustrate the potential of the labels in the colocalization of biological objects and the two-photon activation technique with optical sectioning.
publishDate 2009
dc.date.none.fl_str_mv 2009-10
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/11336/73441
Belov, Vladimir N.; Bossi, Mariano Luis; Fölling, Jonas; Boyarskiy, Vadim P.; Hell, Stefan W.; Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy; Wiley VCH Verlag; Chemistry- A European Journal; 15; 41; 10-2009; 10762-10776
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/73441
identifier_str_mv Belov, Vladimir N.; Bossi, Mariano Luis; Fölling, Jonas; Boyarskiy, Vadim P.; Hell, Stefan W.; Rhodamine spiroamides for multicolor single-molecule switching fluorescent nanoscopy; Wiley VCH Verlag; Chemistry- A European Journal; 15; 41; 10-2009; 10762-10776
0947-6539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200901333
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.200901333
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.070432

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