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Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimagingBiagiotti, Giacomo ...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.Vir: Bioorganic chemistry. - ISSN 0045-2068 (Vol. 109, 2021, str. 1-10)Vrsta gradiva - članek, sestavni del ; neleposlovje za odrasleLeto - 2021Jezik - angleškiCOBISS.SI-ID - 52587523
Avtor
Biagiotti, Giacomo |
Purić, Edvin |
Urbančič, Iztok, fizik |
Krišelj, Ana |
Weiss, Matjaž |
Mravljak, Janez, 1978- |
Gellini, Cristina |
Lay, Luigi |
Chiodo, Fabrizio |
Anderluh, Marko
Teme
Farmacevtska kemija |
BODIPY |
mannose binding lectins |
stimulated emission depletion microscopy |
DC-SIGN |
glycan |
glikan |
bioaktivne molekule |
fluorescenčna mikroskopija |
endosomi |
biomedicinsko slikanje
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Avtor | Biagiotti, Giacomo ... |
Naslov | Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging |
Datum objave | 2021-04-30 |
COBISS.SI-ID | 52587523 |
Verzija objave v repozitoriju | Založnikova različica |
Licenca objave v repozitoriju | Creative Commons Priznanje avtorstva 4.0 Mednarodna |
Embargo | Takojšnja javna objava |
Projekti, iz katerih je bila financirana objava
Naziv | Akronim | Številka projekta | Financer |
---|---|---|---|
Eksperimentalna biofizika kompleksnih sistemov in slikanje v biomedicini | P1-0060-2019 |
Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije |
|
Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin | P1-0208-2015 |
Javna agencija za znanstvenoraziskovalno in inovacijsko dejavnost Republike Slovenije |
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Vnos na polico
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Baze podatkov, v katerih je revija indeksirana
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Povezave do osebnih bibliografij avtorjev | Povezave do podatkov o raziskovalcih v sistemu SICRIS |
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Biagiotti, Giacomo | ![]() |
Purić, Edvin | 55895 |
Urbančič, Iztok, fizik | 32057 |
Krišelj, Ana | 53101 |
Weiss, Matjaž | 50503 |
Mravljak, Janez, 1978- | 23419 |
Gellini, Cristina | ![]() |
Lay, Luigi | ![]() |
Chiodo, Fabrizio | ![]() |
Anderluh, Marko | 21456 |
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