Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging
Copyright © 2021 Elsevier Inc. All rights reserved..
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:109 |
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| Enthalten in: |
Bioorganic chemistry - 109(2021) vom: 05. Apr., Seite 104730 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Biagiotti, Giacomo [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 30.09.2021 Date Revised 30.09.2021 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bioorg.2021.104730 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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NLM321801261 |
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| 245 | 1 | 0 | |a Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2021 Elsevier Inc. All rights reserved. | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a BODIPY | |
| 650 | 4 | |a DC-SIGN | |
| 650 | 4 | |a Glycan | |
| 650 | 4 | |a Mannose binding lectins | |
| 650 | 4 | |a Stimulated emission depletion microscopy | |
| 650 | 7 | |a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene |2 NLM | |
| 650 | 7 | |a Boron Compounds |2 NLM | |
| 650 | 7 | |a Cell Adhesion Molecules |2 NLM | |
| 650 | 7 | |a DC-specific ICAM-3 grabbing nonintegrin |2 NLM | |
| 650 | 7 | |a Lectins, C-Type |2 NLM | |
| 650 | 7 | |a Receptors, Cell Surface |2 NLM | |
| 650 | 7 | |a Glucose |2 NLM | |
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| 650 | 7 | |a Mannose |2 NLM | |
| 650 | 7 | |a PHA4727WTP |2 NLM | |
| 700 | 1 | |a Purić, Edvin |e verfasserin |4 aut | |
| 700 | 1 | |a Urbančič, Iztok |e verfasserin |4 aut | |
| 700 | 1 | |a Krišelj, Ana |e verfasserin |4 aut | |
| 700 | 1 | |a Weiss, Matjaž |e verfasserin |4 aut | |
| 700 | 1 | |a Mravljak, Janez |e verfasserin |4 aut | |
| 700 | 1 | |a Gellini, Cristina |e verfasserin |4 aut | |
| 700 | 1 | |a Lay, Luigi |e verfasserin |4 aut | |
| 700 | 1 | |a Chiodo, Fabrizio |e verfasserin |4 aut | |
| 700 | 1 | |a Anderluh, Marko |e verfasserin |4 aut | |
| 700 | 1 | |a Cicchi, Stefano |e verfasserin |4 aut | |
| 700 | 1 | |a Richichi, Barbara |e verfasserin |4 aut | |
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