n-Octyl (Thio)glycosides as Potential Cryoprotectants: Glass Transition Behaviour, Membrane Permeability, and Ice Recrystallization Inhibition Studies*
Rekha Raju A , Theresa Merl B , Madeleine K. Adam C , Emiliyan Staykov C , Robert N. Ben C , Gary Bryant A D and Brendan L. Wilkinson B D
+ Author Affiliations
- Author Affiliations
A Centre for Molecular and Nanoscale Physics, School of Science, RMIT University, Melbourne, Vic. 3000, Australia.
B School of Science and Technology, University of New England, Armidale, NSW 2351, Australia.
C Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, ON K1N 6N5, Canada.
D Corresponding authors. Email: gary.bryant@rmit.edu.au; brendan.wilkinson@une.edu.au
Australian Journal of Chemistry 72(8) 637-643 https://doi.org/10.1071/CH19159
Submitted: 10 April 2019 Accepted: 25 July 2019 Published: 14 August 2019
Abstract
A series of eight n-octyl (thio)glycosides (1α, β–4α, β) 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, n-octyl β-d-glucopyranoside (2β) exhibited a high glass transition temperatures (Tg), 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.
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