Skip to main page content
Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2018 Jan 22;13(2):133-137.
doi: 10.1002/cmdc.201700744. Epub 2018 Jan 15.

Monosaccharide Derivatives With Low-Nanomolar Lectin Affinity and High Selectivity Based on Combined Fluorine-Amide, Phenyl-Arginine, Sulfur-π, and Halogen Bond Interactions

Affiliations

Monosaccharide Derivatives With Low-Nanomolar Lectin Affinity and High Selectivity Based on Combined Fluorine-Amide, Phenyl-Arginine, Sulfur-π, and Halogen Bond Interactions

Fredrik R Zetterberg et al. ChemMedChem. .

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.

Keywords: fluorine multipolar interactions; galectin-3; halogen bonds; inhibitors; lectins; sulfur-π.

Similar articles

See all similar articles

Cited by 8 articles

See all "Cited by" articles

Publication types

LinkOut - more resources

Feedback