RT Journal Article
T1 Polar ammoniostyryls easily converting a clickable Q1 lipophilic BODIPY in an advanced plasma membrane probe†
A1 Serrano-Buitrago, Sergio
A1 Muñoz Úbeda, Mónica
A1 Almendro Vedia, Víctor Galileo
A1 Sánchez-Camacho, Juan
A1 Lora Maroto, Beatriz
A1 Moreno, Florencio
A1 Bañuelos, Jorge
A1 García-Moreno, Inmaculada
A1 López Montero, Iván
A1 Moya Cerero, Santiago De La
A1 Moreno Jiménez, Florencio
AB 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.
PB The Royal Society of Chemistry
SN 2050-750X
YR 2023
FD 2023
LK https://hdl.handle.net/20.500.14352/92357
UL https://hdl.handle.net/20.500.14352/92357
LA eng
NO Serrano-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.
NO Ministerio de Ciencia, Innovación y Universidades (España)
NO Eusko Jaurlaritza
DS Docta Complutense
RD 6 oct 2024