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Issue 5, 2012
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Potent inhibition of ice recrystallization by low molecular weight carbohydrate-based surfactants and hydrogelators

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Abstract

Ice recrystallization inhibition (IRI) activity is a very desirable property for an effective cryoprotectant. This property was first observed in biological antifreezes (BAs), which cannot be utilized in cryopreservation due to their ability to bind to ice. To date, potent IRI active compounds have been limited to BAs or synthetic C-linked AFGP analogues (1 and 2), all of which are large peptide-based molecules. This paper describes the first example of low molecular weight carbohydrate-based derivatives that exhibit potent IRI activity. Non-ionic surfactant n-octyl-β-D-galactopyranoside (4) exhibited potent IRI activity at a concentration of 22 mM, whereas hydrogelator N-octyl-D-gluconamide (5) exhibited potent IRI activity at a low concentration of 0.5 mM. Thermal hysteresis measurements and solid-state NMR experiments indicated that these derivatives are not exhibiting IRI activity by binding to ice. For non-ionic surfactant derivatives (3 and 4), we demonstrated that carbohydrate hydration is important for IRI activity and that the formation of micelles in solution is not a prerequisite for IRI activity. Furthermore, using solid-state NMR and rheology we demonstrated that the ability of hydrogelators 5 and 6 to form a hydrogel is not relevant to IRI activity. Structure–function studies indicated that the amide bond in 5 is an essential structural feature required for potent IRI activity.

Graphical abstract: Potent inhibition of ice recrystallization by low molecular weight carbohydrate-based surfactants and hydrogelators

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Supplementary files

Article information


Submitted
05 Nov 2011
Accepted
02 Feb 2012
First published
06 Feb 2012

Chem. Sci., 2012,3, 1408-1416
Article type
Edge Article

Potent inhibition of ice recrystallization by low molecular weight carbohydrate-based surfactants and hydrogelators

C. J. Capicciotti, M. Leclère, F. A. Perras, D. L. Bryce, H. Paulin, J. Harden, Y. Liu and R. N. Ben, Chem. Sci., 2012, 3, 1408
DOI: 10.1039/C2SC00885H

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