Eline Bartolami

Abstract Cyclic oligochalcogenides (COCs) are emerging as promising systems to penetrate cells. Clearly better than and different to the reported diselenolanes and epidithiodiketopiperazines, we introduce the benzopolysulfanes (BPS), which show efficient delivery, insensitivity to inhibitors of endocytosis, and compatibility with substrates as large as proteins. This high activity coincides with high reactivity, selectively toward thiols, exceeding exchange rates of disulfides under tension.

Thus far, most of the reported intracellular abiotic catalysis has relied on the catalysts’ inherent cell permeability: only few reports have used cell-permeable carrier modules13, 16, 19, 20. In the absence of a cell-permeable moiety, the efficiency of the catalyst’s cellular uptake has been a matter of controversy14, 35.

The glycosylation of cell-penetrating poly(disulfide)s (CPDs) is introduced to increase the solubility of classical CPDs and to achieve multifunctional cellular uptake. With the recently developed sidechain engineering, CPDs decorated with ?-d-glucose (Glu), ?-d-galactose (Gal), d-trehalose (Tre), and triethyleneglycol (TEG) were readily accessible.