[PMID]: | 29254896 |
[Au] Autor: | Bizet F; Ipuy M; Bernhard Y; Lioret V; Winckler P; Goze C; Perrier-Cornet JM; Decréau RA |
[Ad] Endereço: | ICMUB Institute, University Bourgogne - Franche Comté, 9 Avenue Alain Savary, Sciences Mirande, 21078 Dijon, France. |
[Ti] Título: | Cellular imaging using BODIPY-, pyrene- and phthalocyanine-based conjugates. |
[So] Source: | Bioorg Med Chem;26(2):413-420, 2018 01 15. |
[Is] ISSN: | 1464-3391 |
[Cp] País de publicação: | England |
[La] Idioma: | eng |
[Ab] Resumo: | Fluorescent Probes aimed at absorbing in the blue/green region of the spectrum and emitting in the green/red have been synthesized (as the form of dyads-pentads), studied by spectrofluorimetry, and used for cellular imaging. The synthesis of phthalocyanine-pyrene 1 was achieved by cyclotetramerization of pyrenyldicyanobenzene, whereas phthalocyanine-BODIPY 2c was synthesized by Sonogashira coupling between tetraiodophthalocyanine and meso-alkynylBODIPY. The standard four-steps BODIPY synthesis was applied to the BODIPY-pyrene dyad 3 starting from pyrenecarbaldehyde and dimethylpyrrole. H, C, F, BNMR, ICP, MS, and UV/Vis spectroscopic analyses demonstrated that 2c is a mixture of BODIPY-Pc conjugates corresponding to an average ratio of 2.5 BODIPY per Pc unit, where its bis, tris, tetrakis components could not be separated. Fluorescence emission studies (µM concentration in THF) showed that the design of the probes allowed excitation of their antenna (pyrene, BODIPY) in the blue/green region of the spectrum, and subsequent transfer to the acceptor platform (BODIPY, phthalocyanine) followed by its emission in the green/red (with up to 140-350 nm overall Stokes shifts). The fluorescent probes were used for cellular imaging of B16F10 melanoma cells upon solubilization in 1% DMSO containing RPMI or upon encapsulation in liposomes (injection method). Probes were used at 1-10 µM concentrations, cells were fixed with methanol and imaged by biphoton and/or confocal microscopy, showing that probes could achieve the staining of cells membranes and not the nucleus. |
[Mh] Termos MeSH primário: |
Compostos de Boro/química Corantes Fluorescentes/química Indóis/química Melanoma/diagnóstico Pirenos/química
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[Mh] Termos MeSH secundário: |
Animais Corantes Fluorescentes/síntese química Camundongos Estrutura Molecular Células Tumorais Cultivadas
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[Pt] Tipo de publicação: | JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T |
[Nm] Nome de substância:
| 0 (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene); 0 (Boron Compounds); 0 (Fluorescent Dyes); 0 (Indoles); 0 (Pyrenes); 9E0T7WFW93 (pyrene); V5PUF4VLGY (phthalocyanine) |
[Em] Mês de entrada: | 1802 |
[Cu] Atualização por classe: | 180220 |
[Lr] Data última revisão:
| 180220 |
[Sb] Subgrupo de revista: | IM |
[Da] Data de entrada para processamento: | 171220 |
[St] Status: | MEDLINE |
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