4.6 Review

Bodipy-carbohydrate systems: synthesis and bio-applications

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Summary: The study demonstrates a straightforward synthetic route to water-soluble, uncharged BODIPY derivatives using unprocessed reducing sugar substrates, showing high fluorescence efficiency and compatibility with various postfunctionalizations. The Knoevenagel condensations result in red and far-red fluorescent glycoconjugates with high hydrophilicity, and the synthetic outcome is confirmed through X-ray crystallography and photophysical investigations. Cell experiments further illustrate efficient cell uptake and differential cell targeting based on chiral information integration.

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Boosting the properties of a fluorescent dye by encapsulation into halloysite nanotubes

Serena Riela et al.

Summary: A new biocompatible bichmmophoric system (CURBO) was developed by connecting the skeleton of curcumin to a BODIPY derivative, which showed intense fluorescence and red-shifted emission spectra in organic solvent and aqueous solution, respectively. Loading the system into halloysite nanotubes (HNT) improved its solubility and resulted in increased emission intensity in the red region. The HNT/CURBO nanocomposite exhibited high cell uptake and dual-channel emissions, making it suitable for minimizing autofluorescence detection and interesting microscopy applications.

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Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging

Giacomo Biagiotti et al.

Summary: The synthesis of glyco-BODIPYs 1 and 2 based on efficient chemical reactions allows for efficient targeting of lectins. Glyco-BODIPY 1, with stable C-mannose residues, is effective in targeting DC-SIGN receptors in immune cells. Super-resolution STED microscopy demonstrates that glyco-BODIPY 1 can be used for tracking lectin-mediated cell internalization in diverse biological settings.

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Bringing Color to Sugars: The Chemical Assembly of Carbohydrates to BODIPY Dyes

Ana M. Gomez et al.

Summary: The combination of carbohydrates with BODIPY fluorophores leads to a family of BODIPY-carbohydrate hybrids, with benefits in imaging techniques and biocompatibility. This Account presents available methods for the synthesis of these hybrids, focusing on chemical transformations on the BODIPY core.

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Summary: BODIPY dyes can be turned into efficient triplet photosensitizers with strong absorption in the visible region through proper design strategies such as halogenation of the dye skeleton, donor-acceptor dyads, and BODIPY dimers. These design strategies offer numerous advantages in terms of optical and electrochemical properties, with potential applications ranging from energy conversion to medicine.

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One-Pot Synthesis of Rotationally Restricted, Conjugatable, BODIPY Derivatives from Phthalides

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Syntheses and photodynamic activity of some glucose-conjugated BODIPY dyes

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Cell internalization of BODIPY-based fluorescent dyes bearing carbohydrate residues

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Convenient Access to Carbohydrate-BODIPY Hybrids by Two Complementary Methods Involving One-Pot Assembly of Clickable BODIPY Dyes

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