Glycosylated asterisks are among the most potent low valency inducers of Concanavalin A aggregation

Abstract

A new class of sulfurated, semi-rigid, radial and low-valent glycosylated asterisk ligands with potential dual function as ligand and probe has some of the highest inhibition potencies of Con A-induced hemagglutination, by using a cross-linking mechanism of Con A which amplifies the enhancement to near nanomolar concentrations with the alpha-d-mannose asterisk.

Crystal Multi‐Conformational Control Through Deformable Carbon‐Sulfur Bond for Singlet‐Triplet Emissive Tuning

“…Multi‐sulfurated aromatic compounds are prone to take effect metal‐free room‐temperature phosphorescence emitters in which the ISC process is environmentally adjustable . The compounds can be readily synthesized from low‐cost precursors with different functional groups modified for postprocessing . Herein, we designed and synthesized two fluoro‐substituted tetrakis(arylthio)benzene molecules (compound 1 and 2 , Figure ), based on the anticipation that the multiple C−S bond can be deformable for tuning the molecular conformation with diverse intermolecular non‐covalent interaction (e.g., CH−F bond, CH‐π, S−S interaction, π‐π stacking, etc.).…”

Enhanced Inhibition of Protein Carbohydrate Interactions by Dendritic Multivalent Glycoligands

“…These enhancements of larger systems are not limited to dendrimers since polymers, micelles, quantum dots, and linear glycopolymers were also shown to exhibit these effects (15,16). However there was a report of an exception to these trends, i.e., compound 12, which is both relatively small and of relatively low valency, yet exhibited a very large potency enhancement of 3750-fold per sugar in a hemagglutination inhibition assay in comparison with Me-α-D-glucopyranoside (17). This result indicates that the mechanistic aspects are more complicated even though in general the statistical rebinding mechanism seems to be more effective for larger systems.…”

“…Taken into account that the system is expected to be too small to chelate the binding sites, an explanation involving non-terminal amino acids binding favorably to the protein surface was given as the most likely possibility. (16), P. aeruginosa lectins LecA (17,18) and LecB (19), and their multivalent potency enhancement per sugar, compared to relevant monovalent ligands.…”

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

“…Our investigations further aimed at concentrating a high density of proximate carbohydrate epitopes with limited degrees of freedom onto a sulfurated heteroaromatic scaffold as novel glycosylated asterisk ligands [30]. We have thus designed a simple, yet effective new family of multivalent glycosylated architectures built around a trithiotriazine core.…”