Investigation of α-thioaryl galactopyranosides to improve affinity towards Galectin-9N

Abstract: Galectins are a family of carbohydrate recognition proteins involved in modulation of cell signaling and cell adhesion. galectin-9 especially is involved in regulation of the immune response. In this work, galectin-9N inhibitors have been designed, synthesized and evaluated. The aim was to synthesize compounds with higher affinity than currently known compounds. Three compounds were synthesized with different substituents at the alpha position of the anomeric carbon. Substituent patterns employed in this study were phenyl, methyl phenyl and fluoro phenyl. Affinities of compounds were evaluated in a fluorescence polarization assay. The compound with best affinity was the galectin-9N inhibitor with fluoro phenyl as the substituent, with affinity of 5. The polar interaction between the binding pocket and the inhibitor is believed to be the reason for the good affinity.