Monosaccharide Derivatives with Low-Nanomolar Lectin Affinity and High Selectivity Based on Combined Fluorine-Amide, Phenyl-Arginine, Sulfur-π, and Halogen Bond Interactions
(2018) In ChemMedChem 13(2). p.133-137- Abstract
The design of small and high-affinity lectin inhibitors remains a major challenge because the natural ligand binding sites of lectin are often shallow and have polar character. Herein we report that derivatizing galactose with un-natural structural elements that form multiple non-natural lectin-ligand interactions (orthogonal multipolar fluorine-amide, phenyl-arginine, sulfur-π, and halogen bond) can provide inhibitors with extraordinary affinity (low nanomolar) for the model lectin, galectin-3, which is more than five orders of magnitude higher than the parent galactose; moreover, is selective over other galectins.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/32189061-b29f-4229-a66c-985a0965c316
- author
- Zetterberg, Fredrik R. ; Peterson, Kristoffer LU ; Johnsson, Richard E. LU ; Brimert, Thomas ; Håkansson, Maria LU ; Logan, Derek T. LU ; Leffler, Hakon LU and Nilsson, Ulf J. LU
- organization
- publishing date
- 2018-01-22
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Fluorine multipolar interactions, Galectin-3, Halogen bonds, Inhibitors, Lectins, Sulfur-π
- in
- ChemMedChem
- volume
- 13
- issue
- 2
- pages
- 133 - 137
- publisher
- Wiley-Blackwell
- external identifiers
-
- scopus:85040694778
- pmid:29194992
- ISSN
- 1860-7179
- DOI
- 10.1002/cmdc.201700744
- language
- English
- LU publication?
- yes
- id
- 32189061-b29f-4229-a66c-985a0965c316
- date added to LUP
- 2018-01-30 14:02:33
- date last changed
- 2024-01-29 10:53:35
@article{32189061-b29f-4229-a66c-985a0965c316, abstract = {{<p>The design of small and high-affinity lectin inhibitors remains a major challenge because the natural ligand binding sites of lectin are often shallow and have polar character. Herein we report that derivatizing galactose with un-natural structural elements that form multiple non-natural lectin-ligand interactions (orthogonal multipolar fluorine-amide, phenyl-arginine, sulfur-π, and halogen bond) can provide inhibitors with extraordinary affinity (low nanomolar) for the model lectin, galectin-3, which is more than five orders of magnitude higher than the parent galactose; moreover, is selective over other galectins.</p>}}, author = {{Zetterberg, Fredrik R. and Peterson, Kristoffer and Johnsson, Richard E. and Brimert, Thomas and Håkansson, Maria and Logan, Derek T. and Leffler, Hakon and Nilsson, Ulf J.}}, issn = {{1860-7179}}, keywords = {{Fluorine multipolar interactions; Galectin-3; Halogen bonds; Inhibitors; Lectins; Sulfur-π}}, language = {{eng}}, month = {{01}}, number = {{2}}, pages = {{133--137}}, publisher = {{Wiley-Blackwell}}, series = {{ChemMedChem}}, title = {{Monosaccharide Derivatives with Low-Nanomolar Lectin Affinity and High Selectivity Based on Combined Fluorine-Amide, Phenyl-Arginine, Sulfur-π, and Halogen Bond Interactions}}, url = {{http://dx.doi.org/10.1002/cmdc.201700744}}, doi = {{10.1002/cmdc.201700744}}, volume = {{13}}, year = {{2018}}, }