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

Authors
Type
Published Article
Journal
ChemBioChem
1439-7633
Publisher
Wiley Blackwell (John Wiley & Sons)
Publication Date
Volume
10
Issue
10
Pages
1724–1733
Identifiers
DOI: 10.1002/cbic.200900198
PMID: 19492387
Source
Medline
License
Unknown

Abstract

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.

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