Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/3671227
- author
- van Hattum, Hilde ; Branderhorst, Hilbert M. ; Moret, Ed E. ; Nilsson, Ulf LU ; Leffler, Hakon LU and Pieters, Roland J.
- organization
- publishing date
- 2013
- 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}}, }