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

van Scherpenzee, Monique; Moret, Ed E.; Ballell, Lluis; Liskamp, Rob M. J.; Nilsson, Ulf LU ; Leffler, Hakon LU and Pieters, Roland J. (2009) In ChemBioChem 10(10). p.1724-1733
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 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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
glycoconjugates, galectin-3, carbohydrates, chemical probes, photolabeling
in
ChemBioChem
volume
10
issue
10
pages
1724 - 1733
publisher
John Wiley & Sons
external identifiers
  • wos:000267893200022
  • scopus:70349556437
ISSN
1439-4227
DOI
10.1002/cbic.200900198
language
English
LU publication?
yes
id
0170d540-99b2-4541-bd08-69c7851c90a0 (old id 1462808)
date added to LUP
2009-08-18 16:54:11
date last changed
2017-09-03 03:42:31
@article{0170d540-99b2-4541-bd08-69c7851c90a0,
  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 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.},
  author       = {van Scherpenzee, Monique and Moret, Ed E. and Ballell, Lluis and Liskamp, Rob M. J. and Nilsson, Ulf and Leffler, Hakon and Pieters, Roland J.},
  issn         = {1439-4227},
  keyword      = {glycoconjugates,galectin-3,carbohydrates,chemical probes,photolabeling},
  language     = {eng},
  number       = {10},
  pages        = {1724--1733},
  publisher    = {John Wiley & Sons},
  series       = {ChemBioChem},
  title        = {Synthesis and Evaluation of New Thiodigalactoside-Based Chemical Probes to Label Galectin-3},
  url          = {http://dx.doi.org/10.1002/cbic.200900198},
  volume       = {10},
  year         = {2009},
}