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Synthesis and Evaluation of New Thiodigalactoside-Based Chemical Probes to Label Galectin-3

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Author

Summary, in English

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 be-tween 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.

Publishing year

2009

Language

English

Pages

1724-1733

Publication/Series

ChemBioChem

Volume

10

Issue

10

Document type

Journal article

Publisher

John Wiley & Sons Inc.

Topic

  • Immunology in the medical area
  • Microbiology in the medical area

Keywords

  • glycoconjugates
  • galectin-3
  • carbohydrates
  • chemical probes
  • photolabeling

Status

Published

ISBN/ISSN/Other

  • ISSN: 1439-4227