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

Biagiotti, Giacomo (avtor), Purić, Edvin (avtor), Urbančič, Iztok (avtor), Krišelj, Ana (avtor), Weiss, Matjaž (avtor), Mravljak, Janez (avtor), Gellini, Cristina (avtor), Lay, Luigi (avtor), Chiodo, Fabrizio (avtor), Anderluh, Marko (avtor)

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.

• Jezik: Angleški jezik
• Ključne besede: BODIPY, mannose binding lectins, stimulated emission depletion microscopy, DC-SIGN, glycan
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FFA - Fakulteta za farmacijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2021
• Št. strani: Str. 1-10
• Številčenje: art. 104730, Vol. 109
• PID: 20.500.12556/RUL-144971
• UDK: 615.4:54:615
• ISSN pri članku: 0045-2068
• DOI: 10.1016/j.bioorg.2021.104730
• COBISS.SI-ID: 52587523
• Datum objave v RUL: 27.03.2023

Gradivo je del revije

• Naslov: Bioorganic chemistry
• Skrajšan naslov: Bioorg. chem.
• Založnik: Elsevier
• ISSN: 0045-2068
• COBISS.SI-ID: 25099008

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: glikan, bioaktivne molekule, fluorescenčna mikroskopija, endosomi, biomedicinsko slikanje, farmacevtska kemija