title: Photoswitchable carbohydrate-based fluorosurfactants as tuneable ice recrystallization inhibitors.
abstract: Cryopreservation is an important technique employed for the storage and preservation of biological tissues and cells. The limited effectiveness and significant toxicity of conventionally-used cryoprotectants, such as DMSO, have prompted efforts toward the rational design of less toxic alternatives, including carbohydrate-based surfactants. In this paper, we report the modular synthesis and ice recrystallization inhibition (IRI) activity of a library of variably substituted, carbohydrate-based fluorosurfactants. Carbohydrate-based fluorosurfactants possessed a variable mono- or disaccharide head group appended to a hydrophobic fluoroalkyl-substituted azobenzene tail group. Light-addressable fluorosurfactants displayed weak-to-moderate IRI activity that could be tuned through selection of carbohydrate head group, position of the trifluoroalkyl group on the azobenzene ring, and isomeric state of the azobenzene tail fragment.
authors.affiliation: Department of Chemistry and Biomolecular Sciences, 10 Marie Curie, University of Ottawa, Ontario KN1 6N5, Canada.
authors.forename: Madeleine K
authors.initials: MK
authors.lastname: Adam
authors.affiliation: School of Chemistry, Monash University, Victoria 3800, Australia.
authors.forename: Yingxue
authors.initials: Y
authors.lastname: Hu
authors.affiliation: Department of Chemistry and Biomolecular Sciences, 10 Marie Curie, University of Ottawa, Ontario KN1 6N5, Canada.
authors.forename: Jessica S
authors.initials: JS
authors.lastname: Poisson
authors.affiliation: School of Chemistry, Monash University, Victoria 3800, Australia.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Pottage
authors.affiliation: Department of Chemistry and Biomolecular Sciences, 10 Marie Curie, University of Ottawa, Ontario KN1 6N5, Canada.
authors.forename: Robert N
authors.initials: RN
authors.lastname: Ben
authors.affiliation: School of Science and Technology, University of New England, New South Wales 2351, Australia. Electronic address: bwilkin7@une.edu.au.
authors.forename: Brendan L
authors.initials: BL
authors.lastname: Wilkinson
mesh_terms: D001391:Azo Compounds / Q000737:chemistry; D015925:Cryopreservation; D003451:Cryoprotective Agents / Q000138:chemical synthesis / Q000737:chemistry*; D003460:Crystallization; D004187:Disaccharides / Q000737:chemistry; D054879:Halogenation; D007053:Ice / Q000032:analysis*; D008027:Light; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D055668:Photochemical Processes; D054852:Small Molecule Libraries / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D003451:Cryoprotective Agents; D004187:Disaccharides; D007053:Ice; D009005:Monosaccharides; D054852:Small Molecule Libraries; D013501:Surface-Active Agents
keywords: Carbohydrate-based fluorosurfactants; Ice recrystallization inhibitors; Photoswitchable fluorosurfactants