n-Octyl (Thio)glycosides as Potential Cryoprotectants: Glass Transition Behaviour, Membrane Permeability, and Ice Recrystallization Inhibition Studies

Abstract

A series of eight <i>n</i>-octyl (thio)glycosides (<b>1α, β–4α, β</b>) with D-glucose or D-galactose-configured head groups and varying anomeric configuration were synthesized and evaluated for glass transition behaviour, membrane permeability, and ice recrystallization inhibition (IRI) activity. Of these, <i>n</i>-octyl β-D-glucopyranoside (<b>2β</b>) exhibited a high glass transition temperatures (<i>T_g</i>), both as a neat sample and 20 wt-% aqueous solution. Membrane permeability studies of this compound revealed cellular uptake to concentrations relevant to the inhibition of intracellular ice formation, thus presenting a promising lead candidate for further biophysical and cryopreservation studies. Compounds were also evaluated as ice recrystallization inhibitors; however, no detectable activity was observed for the newly tested compounds.