-
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.Source: Bioorganic chemistry. - ISSN 0045-2068 (Vol. 109, 2021, str. 1-10)Type of material - article, component part ; adult, seriousPublish date - 2021Language - englishCOBISS.SI-ID - 52587523
Author
Biagiotti, Giacomo |
Purić, Edvin |
Urbančič, Iztok, fizik |
Krišelj, Ana |
Weiss, Matjaž |
Mravljak, Janez, 1978- |
Gellini, Cristina |
Lay, Luigi |
Chiodo, Fabrizio |
Anderluh, Marko
Topics
Farmacevtska kemija |
BODIPY |
mannose binding lectins |
stimulated emission depletion microscopy |
DC-SIGN |
glycan |
glikan |
bioaktivne molekule |
fluorescenčna mikroskopija |
endosomi |
biomedicinsko slikanje
Author | Biagiotti, Giacomo ... |
Title | Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging |
Publication date | 2021-04-30 |
COBISS.SI-ID | 52587523 |
Publication version in repository | Publisher's version |
Publication licence | Creative Commons Attribution 4.0 International |
Embargo | Immediate publication for public |
Project(s) from which the publication was funded
Title | Acronym | Project ID | Funder |
---|---|---|---|
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 |
Files that belong to the publication
Shelf entry
Permalink
- URL:
Impact factor
Access to the JCR database is permitted only to users from Slovenia. Your current IP address is not on the list of IP addresses with access permission, and authentication with the relevant AAI accout is required.
Year | Impact factor | Edition | Category | Classification | ||||
---|---|---|---|---|---|---|---|---|
JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
Select the library membership card:
DRS, in which the journal is indexed
Database name | Field | Year |
---|
Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
---|---|
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 |
Select pickup location:
Material pickup by post
Notification
Subject headings in COBISS General List of Subject Headings
Select pickup location
Pickup location | Material status | Reservation |
---|
Please wait a moment.