Polysaccharide-Derived Ice Recrystallization Inhibitors with a Modular Design: The Case of Dextran-Based Graft Polymers.

Ice recrystallization inhibitors inspired from antifreeze proteins (AFPs) are receiving increasing interest for cryobiology and other extreme environment applications. Here, we present a modular strategy to develop polysaccharide-derived biomimetics, and detailed studies were performed in the case of dextran. Poly(vinyl alcohol) (PVA) which has been termed as one of the most potent biomimetics of AFPs was grafted onto dextran via thiol-ene click chemistry (Dex-g-PVA). This demonstrated that Dex-g-PVA is effective in IRI and its activity increases with the degree of polymerization (DP) (sizes of ice crystals were 18.846 ± 1.759 and 9.700 ± 1.920 μm with DPs of 30 and 80, respectively) and fraction of PVA. By means of the dynamic ice shaping (DIS) assay, Dex-g-PVA is found to engage on the ice crystal surfaces, thus the ice affinity accounts for their IRI activity. In addition, Dex- g-PVA displayed enhanced IRI activity compared to that of equivalent PVA alone. We speculate that the hydrophilic nature of dextran would derive PVA in a stretch conformation that favors ice binding. The modular design can not only offer polysaccharides IRI activity but also favor the ice-binding behavior of PVA.

[1]  Zhang Liu,et al.  Bioinspired Ice-Binding Materials for Tissue and Organ Cryopreservation. , 2022, Journal of the American Chemical Society.

[2]  Y. S. Zhang,et al.  Freeform Cell-Laden Cryobioprinting for Shelf-Ready Tissue Fabrication and Storage. , 2021, Matter.

[3]  So-Jung Park,et al.  Hypothermic Stem Cell Storage Using a Polypeptide Thermogel. , 2021, Biomacromolecules.

[4]  Robin Rajan,et al.  Design of an Ice Recrystallization-Inhibiting Polyampholyte-Containing Graft Polymer for Inhibition of Protein Aggregation. , 2021, Biomacromolecules.

[5]  Jun Yang,et al.  Engineering Self-Adhesive Polyzwitterionic Hydrogel Electrolytes for Flexible Zinc-Ion Hybrid Capacitors with Superior Low-Temperature Adaptability. , 2021, ACS nano.

[6]  H. Lee,et al.  Poly(l-Ala-co-l-Lys) Exhibits Excellent Ice Recrystallization Inhibition Activity. , 2021, ACS Macro Letters.

[7]  Fanglian Yao,et al.  Antifreeze proteins and their biomimetics for cell cryopreservation: Mechanism, function and application-A review. , 2021, International journal of biological macromolecules.

[8]  B. Gong,et al.  Dipropinonates of Sugar Alcohols as Water-Soluble, Nontoxic CPAs for DMSO-Free Cell Cryopreservation. , 2021, ACS biomaterials science & engineering.

[9]  S. Matosevic,et al.  Cryopreservation of NK and T Cells Without DMSO for Adoptive Cell-Based Immunotherapy , 2021, BioDrugs.

[10]  Kongchang Wei,et al.  Carbohydrate-Based Macromolecular Biomaterials. , 2021, Chemical reviews.

[11]  So-Jung Park,et al.  Size and Shape Control of Ice Crystals by Amphiphilic Block Copolymers and Their Implication in the Cryoprotection of Mesenchymal Stem Cells. , 2021, ACS applied materials & interfaces.

[12]  M. Gibson,et al.  Polymer Self-Assembly Induced Enhancement of Ice Recrystallization Inhibition , 2021, Journal of the American Chemical Society.

[13]  G. Sosso,et al.  The atomistic details of the ice recrystallisation inhibition activity of PVA , 2021, Nature Communications.

[14]  Gang Zhao,et al.  Ice Inhibition for Cryopreservation: Materials, Strategies, and Challenges , 2021, Advanced science.

[15]  Khoi Vo,et al.  Effects of antioxidants and antifreeze proteins on cryopreservation of blue catfish (Ictalurus furcatus) spermatogonia , 2021 .

[16]  Fanglian Yao,et al.  A starch-based zwitterionic hydrogel coating for blood-contacting devices with durability and bio-functionality , 2021 .

[17]  J. Burdick,et al.  Chemically Modified Biopolymers for the Formation of Biomedical Hydrogels. , 2020, Chemical reviews.

[18]  S. Hyon,et al.  Carboxylated ε-poly-L-lysine, a cryoprotective agent, is an effective partner of ethylene glycol for the vitrification of embryos at various preimplantation stages. , 2020, Cryobiology.

[19]  M. Gibson,et al.  Low DMSO Cryopreservation of Stem Cells Enabled by Macromolecular Cryoprotectants , 2020, ACS applied bio materials.

[20]  S. Hyon,et al.  Molecular design of polyampholytes for vitrification-induced preservation of three-dimensional cell constructs without using liquid nitrogen. , 2020, Biomacromolecules.

[21]  Bingyan Yang,et al.  Bioinspired Cryoprotectants of Glucose-Based Carbon Dots , 2020 .

[22]  S. Lenaghan,et al.  Effect of surface charge density on the ice recrystallization inhibition activity of nanocelluloses. , 2020, Carbohydrate polymers.

[23]  T. Weil,et al.  Polymer bioconjugates: Modern design concepts toward precision hybrid materials , 2020 .

[24]  Liying Yan,et al.  Bioinspired L-Proline Oligomer for the Cryopreservation of Oocytes via Controlling Ice Growth. , 2020, ACS applied materials & interfaces.

[25]  V. Molinero,et al.  Slow Propagation of Ice Binding Limits the Ice-Recrystallization Inhibition Efficiency of PVA and Other Flexible Polymers. , 2020, Journal of the American Chemical Society.

[26]  Yanguang Chen Two Sets of Simple Formulae to Estimating Fractal Dimension of Irregular Boundaries , 2019, Mathematical Problems in Engineering.

[27]  Seungwoo Lee,et al.  Antifreezing Gold Colloids. , 2019, Journal of the American Chemical Society.

[28]  Yi Cao,et al.  Bioinspired Ice Growth Inhibitors Based on Self-Assembling Peptides. , 2019, ACS macro letters.

[29]  Chang Kil Kim,et al.  A brief review of applications of antifreeze proteins in cryopreservation and metabolic genetic engineering , 2019, 3 Biotech.

[30]  Muhammad Hasan,et al.  Mimicking the Ice Recrystallization Activity of Biological Antifreezes. When is a New Polymer “Active”? , 2019, Macromolecular bioscience.

[31]  B. Kong,et al.  Spreading fully at the ice-water interface is required for high ice recrystallization inhibition activity , 2019, Science China Chemistry.

[32]  V. Molinero,et al.  Hydrogen-Bonding and Hydrophobic Groups Contribute Equally to the Binding of Hyperactive Antifreeze and Ice-Nucleating Proteins to Ice. , 2019, Journal of the American Chemical Society.

[33]  C. Brinker,et al.  Metal-Organic Framework Nanoparticle-Assisted Cryopreservation of Red Blood Cells. , 2019, Journal of the American Chemical Society.

[34]  Tianshu Li,et al.  Anomalous Stability of Two-Dimensional Ice Confined in Hydrophobic Nanopores. , 2019, ACS nano.

[35]  A. Gaharwar,et al.  Pectin Methacrylate (PEMA) and Gelatin-Based Hydrogels for Cell Delivery: Converting Waste Materials into Biomaterials. , 2019, ACS applied materials & interfaces.

[36]  Q. Zhong,et al.  Inhibiting Ice Recrystallization by Nanocelluloses. , 2019, Biomacromolecules.

[37]  M. Walker,et al.  Multivalent Presentation of Ice Recrystallization Inhibiting Polymers on Nanoparticles Retains Activity , 2018, Langmuir : the ACS journal of surfaces and colloids.

[38]  Momoh Karmah Mbogba,et al.  Microencapsulation facilitates low-CPA vitrification of HUVECs , 2019 .

[39]  Zhiyuan He,et al.  Bioinspired Materials for Controlling Ice Nucleation, Growth, and Recrystallization. , 2018, Accounts of chemical research.

[40]  F. Paesani,et al.  Ice-Nucleating and Antifreeze Proteins Recognize Ice through a Diversity of Anchored Clathrate and Ice-like Motifs. , 2018, Journal of the American Chemical Society.

[41]  V. Gaukel,et al.  Influence of gelation on ice recrystallization inhibition activity of κ-carrageenan in sucrose solution , 2018 .

[42]  M. Gibson,et al.  Synthesis of Degradable Poly(vinyl alcohol) by Radical Ring-Opening Copolymerization and Ice Recrystallization Inhibition Activity , 2017, ACS macro letters.

[43]  V. Molinero,et al.  Molecular Recognition of Ice by Fully Flexible Molecules , 2017 .

[44]  M. Marcellini,et al.  Polyproline as a Minimal Antifreeze Protein Mimic That Enhances the Cryopreservation of Cell Monolayers , 2017, Angewandte Chemie.

[45]  Jianjun Wang,et al.  Control of ice growth and recrystallization by sulphur-doped oxidized quasi-carbon nitride quantum dots , 2017 .

[46]  M. Gibson,et al.  Ultra-Low Dispersity Poly(vinyl alcohol) Reveals Significant Dispersity Effects on Ice Recrystallization Inhibition Activity. , 2017, ACS macro letters.

[47]  S. MacNeil,et al.  Development of a UV crosslinked biodegradable hydrogel containing adipose derived stem cells to promote vascularization for skin wounds and tissue engineering. , 2017, Biomaterials.

[48]  W. Rao,et al.  Oxidized Quasi‐Carbon Nitride Quantum Dots Inhibit Ice Growth , 2017, Advanced materials.

[49]  R. Notman,et al.  Synthesis of star-branched poly(vinyl alcohol) and ice recrystallization inhibition activity , 2017 .

[50]  Sun-Ha Park,et al.  Marine Antifreeze Proteins: Structure, Function, and Application to Cryopreservation as a Potential Cryoprotectant , 2017, Marine drugs.

[51]  Daniel E. Mitchell,et al.  Structure-activity relationship of the exopolysaccharide from a psychrophilic bacterium: A strategy for cryoprotection. , 2017, Carbohydrate polymers.

[52]  Haiping Fang,et al.  Graphene Oxide Restricts Growth and Recrystallization of Ice Crystals. , 2017, Angewandte Chemie.

[53]  R. Notman,et al.  Influence of Block Copolymerization on the Antifreeze Protein Mimetic Ice Recrystallization Inhibition Activity of Poly(vinyl alcohol) , 2016, Biomacromolecules.

[54]  I. Voets,et al.  Blocking rapid ice crystal growth through nonbasal plane adsorption of antifreeze proteins , 2016, Proceedings of the National Academy of Sciences.

[55]  Daniel E. Mitchell,et al.  Combining Biomimetic Block Copolymer Worms with an Ice‐Inhibiting Polymer for the Solvent‐Free Cryopreservation of Red Blood Cells , 2016, Angewandte Chemie.

[56]  V. Monteil,et al.  Polymerization of ethylene through reversible addition-fragmentation chain transfer (RAFT). , 2014, Angewandte Chemie.

[57]  V. Molinero,et al.  Ice crystallization in ultrafine water-salt aerosols: nucleation, ice-solution equilibrium, and internal structure. , 2014, Journal of the American Chemical Society.

[58]  M. Vatish,et al.  Synthetic polymers enable non-vitreous cellular cryopreservation by reducing ice crystal growth during thawing , 2014, Nature Communications.

[59]  R. Notman,et al.  Ice recrystallisation inhibition by polyols: comparison of molecular and macromolecular inhibitors and role of hydrophobic units. , 2013, Biomaterials science.

[60]  Sung-Ho Kang,et al.  Cryopreservative Effects of the Recombinant Ice-Binding Protein from the Arctic Yeast Leucosporidium sp. on Red Blood Cells , 2012, Applied Biochemistry and Biotechnology.

[61]  T. Koop,et al.  Ice recrystallization inhibition and molecular recognition of ice faces by poly(vinyl alcohol). , 2006, Chemphyschem : a European journal of chemical physics and physical chemistry.

[62]  W. Hennink,et al.  Synthesis, characterization, and polymerization of glycidyl methacrylate derivatized dextran , 1995 .

[63]  T. N. Hansen,et al.  Antifreeze protein modulates cell survival during cryopreservation: mediation through influence on ice crystal growth. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[64]  Joseph H. Finley,et al.  Spectrophotometric determination of polyvinyl alcohol in paper coatings , 1961 .