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Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1

van Hattum, Hilde ; Branderhorst, Hilbert M. ; Moret, Ed E. ; Nilsson, Ulf LU ; Leffler, Hakon LU and Pieters, Roland J. (2013) In Journal of Medicinal Chemistry 56(3). p.1350-1354
Abstract
Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Medicinal Chemistry
volume
56
issue
3
pages
1350 - 1354
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000315182100060
  • scopus:84873903645
ISSN
1520-4804
DOI
10.1021/jm301677r
language
English
LU publication?
yes
id
87790cbe-a99d-4579-82d9-12b0cfbddd2f (old id 3671227)
date added to LUP
2016-04-01 11:13:29
date last changed
2022-03-12 20:43:53
@article{87790cbe-a99d-4579-82d9-12b0cfbddd2f,
  abstract     = {{Inhibitors for galectin-1 and -3 were synthesized from thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The builder 4-(4-phenoxypheny1)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.}},
  author       = {{van Hattum, Hilde and Branderhorst, Hilbert M. and Moret, Ed E. and Nilsson, Ulf and Leffler, Hakon and Pieters, Roland J.}},
  issn         = {{1520-4804}},
  language     = {{eng}},
  number       = {{3}},
  pages        = {{1350--1354}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Medicinal Chemistry}},
  title        = {{Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1}},
  url          = {{http://dx.doi.org/10.1021/jm301677r}},
  doi          = {{10.1021/jm301677r}},
  volume       = {{56}},
  year         = {{2013}},
}