Synthetic Glycosphingolipids for Live-Cell Labeling

Dauner, Martin; Batroff, Ellen; Bachmann, Verena; Hauck, Christof R.; Wittmann, Valentin

Synthetic Glycosphingolipids for Live-Cell Labeling

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Datum

2016

Publikationstyp

Zeitschriftenartikel

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Erschienen in

Bioconjugate Chemistry. 2016, 27(7), pp. 1624-1637. ISSN 1043-1802. eISSN 1520-4812. Available under: doi: 10.1021/acs.bioconjchem.6b00177

Zusammenfassung

Glycosphingolipids are an important component of cell membranes that are involved in many biological processes. Fluorescently labeled glycosphingolipids are frequently used to gain insight into their localization. However, the attachment of a fluorophore to the glycan part or-more commonly-to the lipid part of glycosphingolipids is known to alter the biophysical properties and can perturb the biological function of the probe. Presented here is the synthesis of novel glycosphingolipid probes with mono- and disaccharide head groups and ceramide moieties containing fatty acids of varying chain length (C4 to C20). These glycosphingolipids bear an azide or an alkyne group as chemical reporter to which a fluorophore can be attached through a bioorthogonal ligation reaction. The fluorescent tag and any linker connected to it can be chosen in a flexible manner. We demonstrate the suitability of the probes by selective visualization of the plasma membrane of living cells by confocal microscopy techniques. Whereas the derivatives with the shorter fatty acids can be directly applied to HEK 293T cells, the hydrophobic glycosphingolipids with longer fatty acids can be delivered to cells using fusogenic liposomes.

Fachgebiet (DDC)

540 Chemie

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ISO 690

DAUNER, Martin, Ellen BATROFF, Verena BACHMANN, Christof R. HAUCK, Valentin WITTMANN, 2016. Synthetic Glycosphingolipids for Live-Cell Labeling. In: Bioconjugate Chemistry. 2016, 27(7), pp. 1624-1637. ISSN 1043-1802. eISSN 1520-4812. Available under: doi: 10.1021/acs.bioconjchem.6b00177

BibTex

@article{Dauner2016-07-20Synth-35228,
  year={2016},
  doi={10.1021/acs.bioconjchem.6b00177},
  title={Synthetic Glycosphingolipids for Live-Cell Labeling},
  number={7},
  volume={27},
  issn={1043-1802},
  journal={Bioconjugate Chemistry},
  pages={1624--1637},
  author={Dauner, Martin and Batroff, Ellen and Bachmann, Verena and Hauck, Christof R. and Wittmann, Valentin}
}

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