NDLI: Developing highly active small molecule ice recrystallization inhibitors based upon C-linked antifreeze glycoprotein analogues

Content Provider	Royal Society of Chemistry (RSC)
Author	Capicciotti, Chantelle J. Trant, John F. Ben, Robert N. Biggs, Robyn A.
Copyright Year	2013
Abstract	Ice recrystallization during cryopreservation results in a significant amount of cellular damage making compounds that exhibit ice recrystallization inhibition (IRI) activity desirable as a novel class of cryoprotectants. Herein, we report a systematic structure–function study on a previously identified IRI active C-linked antifreeze glycoprotein (C-AFGP) analogue (1). These studies indicate that while C-AFGPs containing three tripeptide repeats exhibit weak IRI activity 5.5 μM, a minimum number of four tripeptide repeats is required for potent IRI activity at this concentration. In addition, the galactosyl–ornithine building block 5 exhibited only moderate activity at 22 mM, but IRI activity was significantly increased upon addition of two glycine units to the C-terminal end of the amino acid bearing the C-linked galactopyranose residue. Finally, we report that conjugation of long alkyl chains (octyl, nonyl and decyl) to the C-linked galactosyl moiety of 1 can furnish IRI active small molecules. The “ideal” hydrocarbon chain length was 10 carbons for potent activity in this series of compounds. Longer hydrocarbon chain lengths dramatically decreased solubilities. The results of this study emphasize the importance of hydrophobic moieties for IRI activity and while consistent with previously reported small molecule carbohydrate-based and lysine-based ice recrystallization inhibitors, is the first example where a large IRI active glycoconjugate has been successfully truncated to small molecule IRI active components.
Starting Page	26005
Ending Page	26009
Page Count	5
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	3
Issue Number	48
Journal	RSC Advances
DOI	10.1039/c3ra43835j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	IRI Ethylene glycol Hydrocarbon Cryopreservation Carboxylic acid Alkyl Crystallization Glycoprotein Tripeptide Glycoconjugate Glycine C-terminus
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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