Photoswitchable carbohydrate-based fluorosurfactants as tuneable ice recrystallization inhibitors

• Published in: Carbohydrate research 2017-02, Vol.439, p.1-8
• Main Authors: Adam, Madeleine K., Hu, Yingxue, Poisson, Jessica S., Pottage, Matthew J., Ben, Robert N., Wilkinson, Brendan L.
• Format: Article
• Language: English
• Subjects: Azo Compounds - chemistry; Carbohydrate-based fluorosurfactants; Cryopreservation; Cryoprotective Agents - chemical synthesis; Cryoprotective Agents - chemistry; Crystallization; Disaccharides - chemistry; Halogenation; Ice - analysis; Ice recrystallization inhibitors; Light; Molecular Structure; Monosaccharides - chemistry; Photochemical Processes; Photoswitchable fluorosurfactants; Small Molecule Libraries - chemical synthesis; Small Molecule Libraries - chemistry; Structure-Activity Relationship; Surface-Active Agents - chemical synthesis; Surface-Active Agents - chemistry
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2016.12.004

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. [Display omitted] •First report describing the ice recrystallization inhibition (IRI) activity of photoswitchable, carbohydrate-based fluorosurfactants.•6 novel compounds are presented, along with photocontrollable interfacial activity, log P and thermal half-life data.•Attenuation of IRI activity for ortho-CF3 substituted analogues was demonstrated by trans-cis photoisomerization of the photoswitchable tail group.•A carbohydrate-based fluorosurfactant incorporating a D-gluco-configured head group was identified that possessed moderate IRI activity in the cis and trans isomeric states.