20.500.12556/RUL-144971 Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging 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. BODIPY mannose binding lectins stimulated emission depletion microscopy DC-SIGN glycan glikan bioaktivne molekule fluorescenčna mikroskopija endosomi biomedicinsko slikanje farmacevtska kemija true false true Angleški jezik Slovenski jezik Članek v reviji 2023-03-27 07:20:00 2023-03-27 07:20:06 2023-03-28 03:26:51 0000-00-00 00:00:00 2021 0 0 Str. 1-10 Vol. 109 art. 104730 2021 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 615.4:54:615 0045-2068 10.1016/j.bioorg.2021.104730 52587523 1-s2.0-S0045206821001073-main.pdf 1-s2.0-S0045206821001073-main.pdf 1 05D45FD1BF9AC7A3499A08395816E6E7 79bc790c78b7ca6ca356b6abdd229c15433b077765c14bddf41be791c2a43808 e15cfa73-cc5f-11ed-a314-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=167562 https://www.sciencedirect.com/science/article/pii/S0045206821001073?casa_token=HzJ-g6Cn8OUAAAAA:eD-hnCXf40Xf_YPGVDoy1051o5Pc2BOdP8Le6m5lXQ5CROwhvZXT0c-UiHe-5Gf7z60lVhJ6cNEa 1 f213670d-cc5e-11ed-a314-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=167561 Fakulteta za farmacijo 0 0 0