Anthracenemethyl Glycosides as Supramolecular Synthons for Chiral Self-Assembly and as Probes in Cell Imaging.

Abstract

Chiral self-assembly of molecules warrants optimal structural features of synthons that promote formation of such self-assembled structures. A polyaromatic moiety coupled with hydrophilic, chiral-rich carbohydrates leads to segmentation of the regions and the self-assembly to supramolecular structures. Thermodynamic stability is augmented further through chiral self-assembly of the molecules, and formation of the desired chiral supramolecular structures is achieved. In the present study, we develop anthracene glycosides as efficient synthons that, in aqueous solutions, undergo facile self-assembly and lead to chiral supramolecular structures. Anthracenemethyl O-glycosides, installed with mono- and disaccharides, are studied for their self-assembly properties. Emerging chiral structures follow the configuration of the attached sugar moiety. Monosaccharide d- and l-glycopyranoside-containing derivatives alternate between left- and right-handed chiral structures, respectively. Disaccharide-containing derivatives do not exhibit chirality, even when self-assembly occurred. Photochemical [4π + 4π] cycloaddition occurs in the self-assembled structure in aqueous solution. Cell viability assay using HeLa cells shows above 80% viable cells at a concentration of 50 μM. Bioimaging assays reveal a significant imaging of HeLa cells for anthracenemethyl d-glucopyranoside; bright imaging was observed at the perinuclear region of the cells, suggestive of an active transport of the molecules through the cell membrane. d-Galactopyranoside and l-glucopyranoside-containing derivatives show weak imaging potencies.