Polar ammoniostyryls easily converting a clickable Q1 lipophilic BODIPY in an advanced plasma membrane probe†

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dc.contributor.authorSerrano-Buitrago, Sergio
dc.contributor.authorMuñoz Úbeda, Mónica
dc.contributor.authorAlmendro Vedia, Víctor Galileo
dc.contributor.authorSánchez-Camacho, Juan
dc.contributor.authorLora Maroto, Beatriz
dc.contributor.authorMoreno, Florencio
dc.contributor.authorBañuelos, Jorge
dc.contributor.authorGarcía-Moreno, Inmaculada
dc.contributor.authorLópez Montero, Iván
dc.contributor.authorMoya Cerero, Santiago De La
dc.contributor.authorMoreno Jiménez, Florencio
dc.date.accessioned2024-01-10T17:24:33Z
dc.date.available2024-01-10T17:24:33Z
dc.date.issued2023
dc.description.abstractA 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.
dc.description.departmentDepto. de Química Física
dc.description.facultyFac. de Ciencias Químicas
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Ciencia, Innovación y Universidades (España)
dc.description.sponsorshipEusko Jaurlaritza
dc.description.statuspub
dc.identifier.citationSerrano-Buitrago, S.; Muñoz-Úbeda, M.; Almendro-Vedia, V.; Sánchez-Camacho, J.; Maroto, B. L.; Moreno, F.; Bañuelos, J.; García-Moreno, I.; López-Montero, I.; de la Moya, S. Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe. J. Mater. Chem. B 2023, 11, 2108-2114 DOI:10.1039/D2TB02516G.
dc.identifier.doi10.1039/d2tb02516g
dc.identifier.issn2050-750X
dc.identifier.officialurlhttps://doi.org/10.1039/D2TB02516G
dc.identifier.urihttps://hdl.handle.net/20.500.14352/92357
dc.issue.number10
dc.journal.titleJournal of Materials Chemistry B
dc.language.isoeng
dc.page.final2114
dc.page.initial2108
dc.publisherThe Royal Society of Chemistry
dc.rights.accessRightsopen access
dc.subject.cdu54
dc.subject.ucmCiencias
dc.subject.unesco23 Química
dc.titlePolar ammoniostyryls easily converting a clickable Q1 lipophilic BODIPY in an advanced plasma membrane probe†
dc.typejournal article
dc.type.hasVersionP
dc.volume.number11
dspace.entity.typePublication
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relation.isAuthorOfPublication.latestForDiscovery270b8d45-a3ee-4257-8b98-17d43064b34e
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