Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment

Autores
Boyarskiy, Vadim P.; Belov, Vladimir N.; Medda, Rebecca; Hein, Birka; Bossi, Mariano Luis; Hell, Stefan W.
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Highly water soluble fluorescentdyes were synthesized and transformedinto new amino reactive fluorescentlabels for biological microscopy.To this end,rhodamine 8 (preparedfrom 7-hydroxy-1,2,3,4-tetrahydroquinoline(7) and phthalic anhydride in85% aq. H3PO4) was sulfonated with30% SO3 in H2SO4 and afforded thewater soluble disulfonic acid 3a (64%).Amidation of the carboxy group in 3awith 2-(methylamino)ethanol in thepresence of O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium·PF6(HATU) led to alcohol 3b (66%),which was transformed into the aminoreactive mixed carbonate 3d with di(Nsuccinimidyl)carbonate and Et3N. Reactionof the carboxy group in 3a withMeNHACHTUNGTRENUNG(CH2)2CO2Me and N,N,N’,N’-tetramethyl-O-(N-succinimidyl)-uronium·BF4 (TSTU) yielded methylester 13. After saponification of the aliphaticcarboxy group in 13,the compoundwas converted into NHS-ester3e (using HATU and Et3N). Heatingof 7 with trimellitic anhydride inH3PO4 gave a mixture of dicarboxylicacids 14 and 15 (1:1). Regioisomer 15was isolated,sulfonat ed with 30% SO3in H2SO4,and disulfonic acid 3 f wasused for the synthesis of the monoNHS-ester 3g,in which the stericallyunhindered carboxy group was selectivelyactivated (with N-hydroxysuccinimide,HA TU,and Et3N). The sulfonatedrhodamines 3b, c and f are solublein water (up to 0.1m),have excellentphotostabilities and large fluorescencequantum yields. Subdiffractionresolution images of tubulin filamentsof mammalian cells stained with thesedyes illustrate their applicability aslabels for stimulated emission depletionmicroscopy and other fluorescencetechniques.
Fil: Boyarskiy, Vadim P.. Max Planck Institute for Biophysical Chemistry; Alemania. Saint Petersburg State University; Rusia
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Medda, Rebecca. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Hein, Birka. 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. 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
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
Materia
conjugation
dyes/ pigments
fluorescence nanoscopy
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:11336/103208
Acceder
id CONICETDig_55afa6cd8221f72c3549ac2052b12d86
oai_identifier_str oai:ri.conicet.gov.ar:11336/103208
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene FragmentBoyarskiy, Vadim P.Belov, Vladimir N.Medda, RebeccaHein, BirkaBossi, Mariano LuisHell, Stefan W.conjugationdyes/ pigmentsfluorescence nanoscopyrhodamineshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Highly water soluble fluorescentdyes were synthesized and transformedinto new amino reactive fluorescentlabels for biological microscopy.To this end,rhodamine 8 (preparedfrom 7-hydroxy-1,2,3,4-tetrahydroquinoline(7) and phthalic anhydride in85% aq. H3PO4) was sulfonated with30% SO3 in H2SO4 and afforded thewater soluble disulfonic acid 3a (64%).Amidation of the carboxy group in 3awith 2-(methylamino)ethanol in thepresence of O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium·PF6(HATU) led to alcohol 3b (66%),which was transformed into the aminoreactive mixed carbonate 3d with di(Nsuccinimidyl)carbonate and Et3N. Reactionof the carboxy group in 3a withMeNHACHTUNGTRENUNG(CH2)2CO2Me and N,N,N’,N’-tetramethyl-O-(N-succinimidyl)-uronium·BF4 (TSTU) yielded methylester 13. After saponification of the aliphaticcarboxy group in 13,the compoundwas converted into NHS-ester3e (using HATU and Et3N). Heatingof 7 with trimellitic anhydride inH3PO4 gave a mixture of dicarboxylicacids 14 and 15 (1:1). Regioisomer 15was isolated,sulfonat ed with 30% SO3in H2SO4,and disulfonic acid 3 f wasused for the synthesis of the monoNHS-ester 3g,in which the stericallyunhindered carboxy group was selectivelyactivated (with N-hydroxysuccinimide,HA TU,and Et3N). The sulfonatedrhodamines 3b, c and f are solublein water (up to 0.1m),have excellentphotostabilities and large fluorescencequantum yields. Subdiffractionresolution images of tubulin filamentsof mammalian cells stained with thesedyes illustrate their applicability aslabels for stimulated emission depletionmicroscopy and other fluorescencetechniques.Fil: Boyarskiy, Vadim P.. Max Planck Institute for Biophysical Chemistry; Alemania. Saint Petersburg State University; RusiaFil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Medda, Rebecca. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Hein, Birka. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Bossi, Mariano Luis. Max Planck Institute for Biophysical Chemistry; Alemania. 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; ArgentinaFil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; AlemaniaWiley VCH Verlag2008-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/103208Boyarskiy, Vadim P.; Belov, Vladimir N.; Medda, Rebecca; Hein, Birka; Bossi, Mariano Luis; et al.; Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment; Wiley VCH Verlag; Chemistry- A European Journal; 14; 6; 2-2008; 1784-17920947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.200701058info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200701058info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:08:31Zoai:ri.conicet.gov.ar:11336/103208instacron: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 10:08:32.018CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
title Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
spellingShingle Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
Boyarskiy, Vadim P.
conjugation
dyes/ pigments
fluorescence nanoscopy
rhodamines
title_short Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
title_full Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
title_fullStr Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
title_full_unstemmed Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
title_sort Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment
dc.creator.none.fl_str_mv Boyarskiy, Vadim P.
Belov, Vladimir N.
Medda, Rebecca
Hein, Birka
Bossi, Mariano Luis
Hell, Stefan W.
author Boyarskiy, Vadim P.
author_facet Boyarskiy, Vadim P.
Belov, Vladimir N.
Medda, Rebecca
Hein, Birka
Bossi, Mariano Luis
Hell, Stefan W.
author_role author
author2 Belov, Vladimir N.
Medda, Rebecca
Hein, Birka
Bossi, Mariano Luis
Hell, Stefan W.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv conjugation
dyes/ pigments
fluorescence nanoscopy
rhodamines
topic conjugation
dyes/ pigments
fluorescence nanoscopy
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 Highly water soluble fluorescentdyes were synthesized and transformedinto new amino reactive fluorescentlabels for biological microscopy.To this end,rhodamine 8 (preparedfrom 7-hydroxy-1,2,3,4-tetrahydroquinoline(7) and phthalic anhydride in85% aq. H3PO4) was sulfonated with30% SO3 in H2SO4 and afforded thewater soluble disulfonic acid 3a (64%).Amidation of the carboxy group in 3awith 2-(methylamino)ethanol in thepresence of O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium·PF6(HATU) led to alcohol 3b (66%),which was transformed into the aminoreactive mixed carbonate 3d with di(Nsuccinimidyl)carbonate and Et3N. Reactionof the carboxy group in 3a withMeNHACHTUNGTRENUNG(CH2)2CO2Me and N,N,N’,N’-tetramethyl-O-(N-succinimidyl)-uronium·BF4 (TSTU) yielded methylester 13. After saponification of the aliphaticcarboxy group in 13,the compoundwas converted into NHS-ester3e (using HATU and Et3N). Heatingof 7 with trimellitic anhydride inH3PO4 gave a mixture of dicarboxylicacids 14 and 15 (1:1). Regioisomer 15was isolated,sulfonat ed with 30% SO3in H2SO4,and disulfonic acid 3 f wasused for the synthesis of the monoNHS-ester 3g,in which the stericallyunhindered carboxy group was selectivelyactivated (with N-hydroxysuccinimide,HA TU,and Et3N). The sulfonatedrhodamines 3b, c and f are solublein water (up to 0.1m),have excellentphotostabilities and large fluorescencequantum yields. Subdiffractionresolution images of tubulin filamentsof mammalian cells stained with thesedyes illustrate their applicability aslabels for stimulated emission depletionmicroscopy and other fluorescencetechniques.
Fil: Boyarskiy, Vadim P.. Max Planck Institute for Biophysical Chemistry; Alemania. Saint Petersburg State University; Rusia
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Medda, Rebecca. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Hein, Birka. 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. 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
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
description Highly water soluble fluorescentdyes were synthesized and transformedinto new amino reactive fluorescentlabels for biological microscopy.To this end,rhodamine 8 (preparedfrom 7-hydroxy-1,2,3,4-tetrahydroquinoline(7) and phthalic anhydride in85% aq. H3PO4) was sulfonated with30% SO3 in H2SO4 and afforded thewater soluble disulfonic acid 3a (64%).Amidation of the carboxy group in 3awith 2-(methylamino)ethanol in thepresence of O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium·PF6(HATU) led to alcohol 3b (66%),which was transformed into the aminoreactive mixed carbonate 3d with di(Nsuccinimidyl)carbonate and Et3N. Reactionof the carboxy group in 3a withMeNHACHTUNGTRENUNG(CH2)2CO2Me and N,N,N’,N’-tetramethyl-O-(N-succinimidyl)-uronium·BF4 (TSTU) yielded methylester 13. After saponification of the aliphaticcarboxy group in 13,the compoundwas converted into NHS-ester3e (using HATU and Et3N). Heatingof 7 with trimellitic anhydride inH3PO4 gave a mixture of dicarboxylicacids 14 and 15 (1:1). Regioisomer 15was isolated,sulfonat ed with 30% SO3in H2SO4,and disulfonic acid 3 f wasused for the synthesis of the monoNHS-ester 3g,in which the stericallyunhindered carboxy group was selectivelyactivated (with N-hydroxysuccinimide,HA TU,and Et3N). The sulfonatedrhodamines 3b, c and f are solublein water (up to 0.1m),have excellentphotostabilities and large fluorescencequantum yields. Subdiffractionresolution images of tubulin filamentsof mammalian cells stained with thesedyes illustrate their applicability aslabels for stimulated emission depletionmicroscopy and other fluorescencetechniques.
publishDate 2008
dc.date.none.fl_str_mv 2008-02
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/11336/103208
Boyarskiy, Vadim P.; Belov, Vladimir N.; Medda, Rebecca; Hein, Birka; Bossi, Mariano Luis; et al.; Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment; Wiley VCH Verlag; Chemistry- A European Journal; 14; 6; 2-2008; 1784-1792
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/103208
identifier_str_mv Boyarskiy, Vadim P.; Belov, Vladimir N.; Medda, Rebecca; Hein, Birka; Bossi, Mariano Luis; et al.; Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment; Wiley VCH Verlag; Chemistry- A European Journal; 14; 6; 2-2008; 1784-1792
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/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.200701058
info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.200701058
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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