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

In English

Författare

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.

Publiceringsår

2009

Språk

Engelska

Sidor

1724-1733

Publikation/Tidskrift/Serie

ChemBioChem

Volym

10

Issue

10

Dokumenttyp

Artikel i tidskrift

Förlag

John Wiley & Sons Inc.

Ämne

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

Nyckelord

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

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 1439-4227