Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe

A very simple, small and symmetric, but highly bright, photostable and functionalizable molecular probe for plasma membrane (PM) has been developed from an accessible, lipophilic and clickable organic dye based on BODIPY. To this aim, two lateral polar ammoniostyryl groups were easily linked to incr...

Descripción completa

Detalles Bibliográficos
Autores: Serrano-Buitrago, Sergio, Muñoz Úbeda, Mónica, Almendro Vedia, Víctor Galileo, Sánchez-Camacho, Juan, Lora Maroto, Beatriz, Moreno Jiménez, Florencio, Bañuelos, Jorge, García-Moreno, Inmaculada, López Montero, Iván, Moya Cerero, Santiago de la
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/92357
Acceso en línea:https://hdl.handle.net/20.500.14352/92357
Access Level:acceso abierto
Palabra clave:54
Ciencias
23 Química
id ES_3b85b72e4ca6df20428fddbf17c8d913
oai_identifier_str oai:docta.ucm.es:20.500.14352/92357
network_acronym_str ES
network_name_str España
repository_id_str
spelling Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probeSerrano-Buitrago, SergioMuñoz Úbeda, MónicaAlmendro Vedia, Víctor GalileoSánchez-Camacho, JuanLora Maroto, BeatrizMoreno Jiménez, FlorencioBañuelos, JorgeGarcía-Moreno, InmaculadaLópez Montero, IvánMoya Cerero, Santiago de la54Ciencias23 QuímicaA very simple, small and symmetric, but highly bright, photostable and functionalizable molecular probe for plasma membrane (PM) has been developed from an accessible, lipophilic and clickable organic dye based on BODIPY. To this aim, two lateral polar ammoniostyryl groups were easily linked to increase the amphiphilicity of the probe and thus its lipid membrane partitioning. Compared to the BODIPY precursor, the transversal diffusion across lipid bilayers of the ammoniostyryled BODIPY probe was highly reduced, as evidenced by fluorescence confocal microscopy on model membranes built up as giant unilamellar vesicles (GUVs). Moreover, the ammoniostyryl groups endow the new BODIPY probe with the ability to optically work (excitation and emission) in the bioimaging-useful red region, as shown by staining of the plasma membrane of living mouse embryonic fibroblasts (MEFs). Upon incubation, this fluorescent probe rapidly entered the cell through the endosomal pathway. By blocking the endocytic trafficking at 4 °C, the probe was confined within the PM of MEFs. Our experiments show the developed ammoniostyrylated BODIPY as a suitable PM fluorescent probe, and confirm the synthetic approach for advancing PM probes, imaging and science.The Royal Society of ChemistryUniversidad Complutense de Madrid20232023-01-0120232023-01-01journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/92357reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/923572026-06-02T12:44:21Z
dc.title.none.fl_str_mv Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
title Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
spellingShingle Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
Serrano-Buitrago, Sergio
54
Ciencias
23 Química
title_short Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
title_full Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
title_fullStr Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
title_full_unstemmed Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
title_sort Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
dc.creator.none.fl_str_mv Serrano-Buitrago, Sergio
Muñoz Úbeda, Mónica
Almendro Vedia, Víctor Galileo
Sánchez-Camacho, Juan
Lora Maroto, Beatriz
Moreno Jiménez, Florencio
Bañuelos, Jorge
García-Moreno, Inmaculada
López Montero, Iván
Moya Cerero, Santiago de la
author Serrano-Buitrago, Sergio
author_facet Serrano-Buitrago, Sergio
Muñoz Úbeda, Mónica
Almendro Vedia, Víctor Galileo
Sánchez-Camacho, Juan
Lora Maroto, Beatriz
Moreno Jiménez, Florencio
Bañuelos, Jorge
García-Moreno, Inmaculada
López Montero, Iván
Moya Cerero, Santiago de la
author_role author
author2 Muñoz Úbeda, Mónica
Almendro Vedia, Víctor Galileo
Sánchez-Camacho, Juan
Lora Maroto, Beatriz
Moreno Jiménez, Florencio
Bañuelos, Jorge
García-Moreno, Inmaculada
López Montero, Iván
Moya Cerero, Santiago de la
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 54
Ciencias
23 Química
topic 54
Ciencias
23 Química
description A very simple, small and symmetric, but highly bright, photostable and functionalizable molecular probe for plasma membrane (PM) has been developed from an accessible, lipophilic and clickable organic dye based on BODIPY. To this aim, two lateral polar ammoniostyryl groups were easily linked to increase the amphiphilicity of the probe and thus its lipid membrane partitioning. Compared to the BODIPY precursor, the transversal diffusion across lipid bilayers of the ammoniostyryled BODIPY probe was highly reduced, as evidenced by fluorescence confocal microscopy on model membranes built up as giant unilamellar vesicles (GUVs). Moreover, the ammoniostyryl groups endow the new BODIPY probe with the ability to optically work (excitation and emission) in the bioimaging-useful red region, as shown by staining of the plasma membrane of living mouse embryonic fibroblasts (MEFs). Upon incubation, this fluorescent probe rapidly entered the cell through the endosomal pathway. By blocking the endocytic trafficking at 4 °C, the probe was confined within the PM of MEFs. Our experiments show the developed ammoniostyrylated BODIPY as a suitable PM fluorescent probe, and confirm the synthetic approach for advancing PM probes, imaging and science.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-01-01
2023
2023-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/92357
url https://hdl.handle.net/20.500.14352/92357
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv The Royal Society of Chemistry
publisher.none.fl_str_mv The Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869406311624474624
score 15,300724

Similares en LA Referencia