Fluorescent probes are of enormous importance in biomedical research and medical imaging. Most currently used probes for activated macrophages target the recognition of enzymes or cell surface receptors. The BODIPY scaffold is one of the most exploited fluorophores, due to its excellent photophysical properties. While BODIPY dyes have been widely used to label biomolecules and prepare the corresponding fluorescent analogues, there are few reports of activatable fluorescent probes based on the BODIPY scaffold.
Multicomponent reactions (MCRs) are excellent chemical tools to generate complex derivatives with unique chemical diversity. University researchers achieved the first derivatization of the BODIPY structure using MCRs, and prepared a collection of activatable fluorescent BODIPY probes with exclusive chemical connectivity and good cell permeability. They examined their collection of BODIPY adducts in live cell imaging and identified one derivative, named as PhagoGreen, as a highly fluorescent activatable probe for phagocytic macrophages.
PhagoGreen is a pH-sensitive probe that brightly stains acidified phagosomes in macrophages. The staining of PhagoGreen is proportional to the extent of the treatment with zymosan, a glucan from yeast cell wall that induces phagosomal acidification, proving that its fluorescence emission correlates with the degree of macrophage activation.
Research has corroborated that PhagoGreen is not cytotoxic and does not impair the normal physiology of macrophages, and it to image phagocytic macrophages in vivo in zebrafish embryos.
- Biomedical research
- Medical imaging
- requires a lower concentration
- potentially less toxic than alternative offerings
- brighter probe, so easier to track the behaviour and distribution of the macrophages
- pH sensitive
- targeted at macrophages
Multicomponent Reactions for de Novo Synthesis of BODIPY Probes: In Vivo Imaging of Phagocytic Macrophages, J. Am. Chem. Soc., 2013, 135 (43), pp 16018–16021
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