Synthesis and evaluation of new thiodigalactoside-based chemical probes to label galectin-3

van Scherpenzeel, M., Moret, E.E., Ballell, L., Liskamp, R.M.J. , Nilsson, U.J., Leffler, H. and Pieters, R.J. (2009) Synthesis and evaluation of new thiodigalactoside-based chemical probes to label galectin-3. ChemBioChem, 10(10), pp. 1724-1733. (doi:10.1002/cbic.200900198)

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Abstract

Light up galectin: Photoprobes based on thiodigalactoside were prepared for galectin-3, a lectin linked to cancer. The probes contained either benzophenone or acetophenone moieties as the photolabel for covalent attachment to the protein. One particular probe labeled galectin-3 selectively, even in the presence of cell lysate.

New chemical probes were synthesized to label galectin-3. They are based on the high affinity thiodigalactoside ligand. The probes were synthesized with benzophenone or acetophenone moieties as the photolabel for covalent attachment to the protein. Besides labeling the protein, these aromatic photolabels also greatly enhance the affinity of the probes towards galectin-3, due to the interaction of the photolabel with two arginine guanidinium groups of the protein. The linkage between the sugar and the photolabel was varied as an ester, an amide, and a triazole. For the amide and triazole derivatives, a versatile synthetic route towards a symmetrical 3-azido-3-deoxy-thiodigalactoside was developed. The new probes were evaluated for their binding affinity of human galectin-3. They were subsequently tested for their labeling efficiency, as well as specificity in the presence of a protein mixture and a human cancer cell lysate.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: van Scherpenzeel, M., Moret, E.E., Ballell, L., Liskamp, R.M.J., Nilsson, U.J., Leffler, H., and Pieters, R.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:ChemBioChem
ISSN:1439-4227
ISSN (Online):1439-7633

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