Polar ammoniostyryls easily converting a clickable lipophilic BODIPY in an advanced plasma membrane probe
| Autor: | Sergio Serrano-Buitrago, Mónica Muñoz-Úbeda, Víctor G. Almendro-Vedia, Juan Sánchez-Camacho, Beatriz L. Maroto, Florencio Moreno, Jorge Bañuelos, Inmaculada García-Moreno, Iván López-Montero, Santiago de la Moya |
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| Přispěvatelé: | Ministerio de Ciencia e Innovación (España), Eusko Jaurlaritza, Ministerio de Ciencia, Innovación y Universidades (España), Comunidad de Madrid, Ministerio de Sanidad (España) |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Journal of Materials Chemistry B 11: 2108-2114 (2023). |
| ISSN: | 2050-7518 |
| Popis: | 7 pags., 5 figs. 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. Financial support from MICINN (PID2020-114755GB-C31, -C32 and C-33) and Basque Government (IT1639-22) is gratefully acknowledged by S. d. l. M., J. B. and I. G.-M. I. L.-M. acknowledge financial support from the Spanish Ministry of Science, Innovation and Universities through the grant PGC2018-097903-B-I00. This work was also supported by the TECNOLOGI´AS 2018 program, funded by the Regional Government of Madrid (Grant S2018/BAA-4403 SINOXPHOS-CM, to I. L-M.). S. S.-B. thanks the Regional Government of Madrid for an INVESTIGO contract. M. M.-U´. was recipient of a Sara Borrell fellowship (CD15/00190) financed by the Spanish Ministry of Health. |
| Databáze: | OpenAIRE |
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