Copper-free click reactions with polar bicyclononyne derivatives for modulation of cellular imaging
| Autor: | F.L. van Delft, Jan Dommerholt, Joost G. J. Hoenderop, Elizabeth H. P. Leunissen, Jorge M. M. Verkade, M. H. L. Meuleners |
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| Rok vydání: | 2014 |
| Předmět: |
Azides
Glycan Glycosylation Cycloalkyne Synthetic Organic Chemistry Biochemistry Bridged Bicyclo Compounds chemistry.chemical_compound Polysaccharides Labelling Humans Organic chemistry Moiety Hydroxymethyl Molecular Biology Fluorescent Dyes Microscopy Confocal Cycloaddition Reaction biology Optical Imaging Organic Chemistry Flow Cytometry Combinatorial chemistry Cycloaddition HEK293 Cells Renal disorders Radboud Institute for Molecular Life Sciences [Radboudumc 11] chemistry Alkynes biology.protein Click chemistry Molecular Medicine Click Chemistry Azide |
| Zdroj: | ChemBioChem, 15, 10, pp. 1446-51 ChemBioChem, 15, 1446-1451 ChemBioChem, 15, 1446-51 ChemBioChem, 15, 10, pp. 1446-1451 |
| ISSN: | 1439-4227 |
| Popis: | Contains fulltext : 137694.pdf (Publisher’s version ) (Closed access) The ability of cells to incorporate azidosugars metabolically is a useful tool for extracellular glycan labelling. The exposed azide moiety can covalently react with alkynes, such as bicyclo[6.1.0]nonyne (BCN), by strain-promoted alkyne-azide cycloaddition (SPAAC). However, the use of SPAAC can be hampered by low specificity of the cycloalkyne. In this article we describe the synthesis of more polar BCN derivatives and their properties for selective cellular glycan labelling. The new polar derivatives [amino-BCN, glutarylamino-BCN and bis(hydroxymethyl)-BCN] display reaction rates similar to those of BCN and are less cell-permeable. The labelling specificity in HEK293 cells is greater than that of BCN, as determined by confocal microscopy and flow cytometry. Interestingly, amino-BCN appears to be highly specific for the Golgi apparatus. In addition, the polar BCN derivatives label the N-glycan of the membrane calcium channel TRPV5 in HEK293 cells with significantly enhanced signal-to-noise ratios. |
| Databáze: | OpenAIRE |
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