1. Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging
- Author
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Fabrizio Chiodo, Giacomo Biagiotti, Edvin Purić, Stefano Cicchi, Cristina Gellini, Luigi Lay, Marko Anderluh, Matjaž Weiss, Barbara Richichi, Janez Mravljak, Iztok Urbančič, Ana Krišelj, and Molecular cell biology and Immunology
- Subjects
glikan ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,stimulated emission depletion microscopy ,Drug Discovery ,Fluorescence microscope ,Internalization ,udc:615.4 ,media_common ,glycan ,biology ,Molecular Structure ,Chemistry ,STED microscopy ,Healthy Volunteers ,DC-SIGN ,fluorescenčna mikroskopija ,glikan, bioaktivne molekule, fluorescenčna mikroskopija, endosomi, biomedicinsko slikanje ,Knoevenagel condensation ,BODIPY ,udc:615.4:54:615 ,Boron Compounds ,Endosome ,media_common.quotation_subject ,Farmacevtska kemija ,Receptors, Cell Surface ,Cell Line ,Structure-Activity Relationship ,Humans ,endosomi ,Lectins, C-Type ,Molecular Biology ,Dose-Response Relationship, Drug ,010405 organic chemistry ,Organic Chemistry ,Lectin ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,bioaktivne molekule ,Glucose ,Biophysics ,biology.protein ,farmacevtska kemija ,BODIPY, mannose binding lectins, stimulated emission depletion microscopy, DC-SIGN, glycan ,mannose binding lectins ,Cell Adhesion Molecules ,Mannose ,biomedicinsko slikanje - Abstract
Lectins are involved in a wide range of carbohydrate mediated recognition processes. Therefore, the availability of highly performant fluorescent tools tailored for lectin targeting and able to efficiently track events related to such key targets is in high demand. We report here on the synthesis of the glyco-BODIPYs 1 and 2, based on the efficient combination of a Heck-like cross coupling and a Knoevenagel condensation, which revealed efficient in addressing lectins. In particular, glyco-BODIPY 1 has two glycosidase stable C-mannose residues, which act as DC-SIGN (dendritic cell-specific intercellular adhesion molecule-3-grabbing non-integrin) targeting modules. By using live-cell fluorescence microscopy, we proved that BODIPY-mannose 1 was efficiently taken up by immune cells expressing DC-SIGN receptors. Super-resolution stimulated emission depletion (STED) microscopy further revealed that the internalized 1 localized in membranes of endosomes, proving that 1 is a reliable tool also in STED applications. Of note, glyco-BODIPY 1 contains an aryl-azido group, which allows further functionalization of the glycoprobe with bioactive molecules, thus paving the way for the use of 1 for tracking lectin-mediated cell internalization in diverse biological settings. Članek s št.: 104730. Abstract. Bibliografija: str. 9-10. ARRS ARRS
- Published
- 2021
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