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

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

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.

• Language: English
• Keywords: BODIPY, mannose binding lectins, stimulated emission depletion microscopy, DC-SIGN, glycan
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FFA - Faculty of Pharmacy
• Publication status: Published
• Publication version: Version of Record
• Year: 2021
• Number of pages: Str. 1-10
• Numbering: art. 104730, Vol. 109
• PID: 20.500.12556/RUL-144971
• UDC: 615.4:54:615
• ISSN on article: 0045-2068
• DOI: 10.1016/j.bioorg.2021.104730
• COBISS.SI-ID: 52587523
• Publication date in RUL: 27.03.2023

Record is a part of a journal

• Title: Bioorganic chemistry
• Shortened title: Bioorg. chem.
• Publisher: Elsevier
• ISSN: 0045-2068
• COBISS.SI-ID: 25099008

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: glikan, bioaktivne molekule, fluorescenčna mikroskopija, endosomi, biomedicinsko slikanje, farmacevtska kemija