Multicomponent Reactions for de Novo Synthesis of BODIPY Probes: In Vivo Imaging of Phagocytic Macrophages.

Multicomponent reactions are excellent tools to generate complex structures with broad chemical diversity and fluorescent properties. Herein we describe the adaptation of the fluorescent BODIPY scaffold to multicomponent reaction chemistry with the synthesis of BODIPY adducts with high fluorescence...

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Publicado en:Journal of the American Chemical Society Vol. 135; no. 43; pp. 16018 - 16022
Autores principales: Vázquez-Romero, Ana, Kielland, Nicola, Arévalo, María J., Preciado, Sara, Mellanby, Richard J., Yi Feng, Lavilla, Rodolfo, Vendrell, Marc
Formato: Artículo
Publicado: American Chemical Society 10/30/2013
Materias:
Acceso en línea:Ver este registro en EBSCOhost
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        atl: Multicomponent Reactions for de Novo Synthesis of BODIPY Probes: In Vivo Imaging of Phagocytic Macrophages.
      aug:
        au:
          Vázquez-Romero, Ana
          Kielland, Nicola
          Arévalo, María J.
          Preciado, Sara
          Mellanby, Richard J.
          Yi Feng
          Lavilla, Rodolfo
          Vendrell, Marc
        affil:
          Barcelona Science Park, Baldiri Reixac 10-12, 08028 Barcelona, Spain
          Escuela Politécnica, Universidad Extremadura, Avda. de la Universidad s/n, 10003 Cáceres, Spain
          MRC Centre for Inflammation Research, Queen's Medical Research Institute, University of Edinburgh, Edinburgh EH16 4TJ, United Kingdom
          Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Avda. Joan XXIII s/n, 08028 Barcelona, Spain
      su:
        Imaging systems
        Chemical synthesis
        Macrophage activation
        Acidification
        Dyes & dyeing
        Fluorescent dyes
      sug:
        subj:
          Imaging systems
          Chemical synthesis
          Macrophage activation
          Acidification
          Dyes & dyeing
          Fluorescent dyes
      ab: Multicomponent reactions are excellent tools to generate complex structures with broad chemical diversity and fluorescent properties. Herein we describe the adaptation of the fluorescent BODIPY scaffold to multicomponent reaction chemistry with the synthesis of BODIPY adducts with high fluorescence quantum yields and good cell permeability. From this library we identified one BODIPY derivative (PhagoGreen) as a low-pH sensing fluorescent probe that enabled imaging of phagosomal acidification in activated macrophages. The fluorescence emission of PhagoGreen was proportional to the degree of activation of macrophages and could be specifically blocked by bafilomycin A, an inhibitor of phagosomal acidification. PhagoGreen does not impair the normal functions of macrophages and can be used to image phagocytic macrophages in vivo.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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          year: 2013
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