Bioorganic Chemistry, volume 109, pages 104730
Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging.
Biagiotti Giacomo
1
,
Purić Edvin
2
,
Urbančič Iztok
3
,
Krišelj Ana
3
,
Weiss M
2
,
Mravljak Janez
2
,
Gellini Cristina
1
,
Lay Luigi
4
,
Chiodo Fabrizio
,
Anderluh Marko
5
,
Cicchi Stefano
6
,
Richichi Barbara
6
1
Dept. of Chemistry Ugo Schiff, University of Firenze, Via Della Lastruccia 3-13, 50019, Sesto Fiorentino, Fi, Italy
|
2
University of Ljubljana, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Aškerčeva 7, SI-1000 Ljubljana, Slovenia.
|
3
Laboratory of Biophysics, Condensed Matter Physics, Department Jožef Stefan Institute, Jamova cesta 39, SI-1000 Ljubljana, Slovenia.
|
5
University of Ljubljana
|
6
Univ of Florence
Publication type: Journal Article
Publication date: 2021-04-01
Journal:
Bioorganic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.1
ISSN: 00452068, 10902120
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Abstract
• Get fluorescent glyco-BODIPYs by the combination of a Heck-like cross coupling and a Knoevenagel condensation. • The glycosidase stable BODIPY-mannose acts as efficient DC-SIGN targeting probes in vitro. • BODIPY-mannose: a high performant tool in fluorescence and STED microscopy. • The functional and modular glyco-probe can be further functionalized with bioactive compounds. • Significant perspectives on tracking lectin-mediated cell uptake in diverse biological settings. 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.
Citations by journals
|
1
2
|
|
|
Chemical Society Reviews
|
Chemical Society Reviews
2 publications, 20%
|
|
Molecules
|
Molecules
1 publication, 10%
|
|
Pure and Applied Chemistry
|
Pure and Applied Chemistry
1 publication, 10%
|
|
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
|
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
1 publication, 10%
|
|
2D Materials
|
2D Materials
1 publication, 10%
|
|
Chemical Record
|
Chemical Record
1 publication, 10%
|
|
Advanced Materials
|
Advanced Materials
1 publication, 10%
|
|
Organic and Biomolecular Chemistry
|
Organic and Biomolecular Chemistry
1 publication, 10%
|
|
Journal of Organic Chemistry
|
Journal of Organic Chemistry
1 publication, 10%
|
|
1
2
|
Citations by publishers
|
1
2
3
|
|
|
Royal Society of Chemistry (RSC)
|
Royal Society of Chemistry (RSC)
3 publications, 30%
|
|
Wiley
|
Wiley
2 publications, 20%
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
|
Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 10%
|
|
Walter de Gruyter
|
Walter de Gruyter
1 publication, 10%
|
|
Elsevier
|
Elsevier
1 publication, 10%
|
|
IOP Publishing
|
IOP Publishing
1 publication, 10%
|
|
American Chemical Society (ACS)
|
American Chemical Society (ACS)
1 publication, 10%
|
|
1
2
3
|
- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2021,2022,2023,2024],"ids":[0,0,0,0],"codes":[0,0,0,0],"imageUrls":["","","",""],"datasets":[{"label":"Citations number","data":[1,4,4,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["10","40","40","10"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Chemical Society Reviews","Molecules","Pure and Applied Chemistry","Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy","2D Materials","Chemical Record","Advanced Materials","Organic and Biomolecular Chemistry","Journal of Organic Chemistry"],"ids":[20586,1770,11456,6337,22357,22413,25159,541,8697],"codes":[0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/3SpVxcYL33bOvPq4sHxJLH2NeKNeDloahSUpNiO4_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/LsKy6OnmmmRGcAU6CZgWQvNiP1polbaSLNrN7zqj_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp"],"datasets":[{"label":"","data":[2,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[20,10,10,10,10,10,10,10,10],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Royal Society of Chemistry (RSC)","Wiley","Multidisciplinary Digital Publishing Institute (MDPI)","Walter de Gruyter","Elsevier","IOP Publishing","American Chemical Society (ACS)"],"ids":[123,11,202,4,17,2075,40],"codes":[0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/3SpVxcYL33bOvPq4sHxJLH2NeKNeDloahSUpNiO4_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/LsKy6OnmmmRGcAU6CZgWQvNiP1polbaSLNrN7zqj_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp"],"datasets":[{"label":"","data":[3,2,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[30,20,10,10,10,10,10],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"}},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"}}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Metrics
Cite this
GOST |
RIS |
BibTex
Cite this
GOST
Copy
Biagiotti G. et al. Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging. // Bioorganic Chemistry. 2021. Vol. 109. p. 104730.
GOST all authors (up to 50)
Copy
Biagiotti G., Purić E., Urbančič I., Krišelj A., Weiss M., Mravljak J., Gellini C., Lay L., Chiodo F., Anderluh M., Cicchi S., Richichi B. Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging. // Bioorganic Chemistry. 2021. Vol. 109. p. 104730.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.bioorg.2021.104730
UR - https://doi.org/10.1016%2Fj.bioorg.2021.104730
TI - Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging.
T2 - Bioorganic Chemistry
AU - Biagiotti, Giacomo
AU - Purić, Edvin
AU - Urbančič, Iztok
AU - Krišelj, Ana
AU - Weiss, M
AU - Mravljak, Janez
AU - Gellini, Cristina
AU - Lay, Luigi
AU - Chiodo, Fabrizio
AU - Anderluh, Marko
AU - Cicchi, Stefano
AU - Richichi, Barbara
PY - 2021
DA - 2021/04/01 00:00:00
PB - Elsevier
SP - 104730
VL - 109
SN - 0045-2068
SN - 1090-2120
ER -
Cite this
BibTex
Copy
@article{2021_Biagiotti,
author = {Giacomo Biagiotti and Edvin Purić and Iztok Urbančič and Ana Krišelj and M Weiss and Janez Mravljak and Cristina Gellini and Luigi Lay and Fabrizio Chiodo and Marko Anderluh and Stefano Cicchi and Barbara Richichi},
title = {Combining cross-coupling reaction and Knoevenagel condensation in the synthesis of glyco-BODIPY probes for DC-SIGN super-resolution bioimaging.},
journal = {Bioorganic Chemistry},
year = {2021},
volume = {109},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016%2Fj.bioorg.2021.104730},
pages = {104730},
doi = {10.1016/j.bioorg.2021.104730}
}