Binding of β-amyloid to sulfated sugar residues in a polymer brush

Kitano, Hiromi; Saito, Daisuke; Kamada, Tomohiro; Gemmei‐Ide, Makoto

doi:10.1016/j.colsurfb.2012.01.010

Cited by 11 publications

(6 citation statements)

References 56 publications

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“…This method has the advantage that the polymer can be fully characterized and preliminary tests can be performed before the immobilization step is conducted. The immobilization is achieved often via reaction of a thiol endgroup with a gold surface . However, for the synthesis of functionalized surfaces for biological applications like affinity chromatography, flat gold surface or gold nanoparticles are not the best choice due to the low surface area and the high costs, respectively.…”

Section: Introductionmentioning

confidence: 99%

“…The immobilization is achieved often via reaction of a thiol endgroup with a gold surface. [29][30][31] However, for the synthesis of functionalized surfaces for biological applications like affi nity chromatography, fl at gold surface or gold nanoparticles are not the best choice due to the low surface area and the high costs, respectively. If other types of surfaces like polystyrene or silica beads are targeted, different strategies have to be followed to couple a glycopolymer onto the surface, for example, applying the azide-alkyne click reaction, [ 32 ] the isocyanate coupling to an amino groups bearing surface [ 33 ] or the thiol-ene reaction.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Thermoresponsive Glycopolymers Combining RAFT Polymerization, Thiol‐Ene Reaction, and Subsequent Immobilization onto Solid Supports

Ehe

Weber

Wagner

et al. 2014

Macro Chemistry & Physics

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A new monomer, N‐hexenylacrylamide, is copolymerized with N‐isopropylacrylamide by reversible addition‐fragmentation chain transfer (RAFT) polymerization using a carboxylic‐acid‐functionalized RAFT agent. Subsequently, the resulting functional copolymers are reacted with acetylated thiogalactose via a thiol‐ene reaction. After deprotection of the sugar acetyl groups, the glycopolymers show a lower critical solution temperature (LCST) behavior, as confirmed by turbidity measurements. One of these glycopolymers is subsequently immobilized onto solid supports. The obtained products are characterized by attenuated total reflection Fourier transform IR (ATR FTIR) spectroscopy, thermal gravimmetric analysis (TGA), and elemental analysis, confirming the immobilization of the glycopolymer. Additionally, the glycopolymer‐functionalized support shows interaction with the lectin RCA120.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Thermoresponsive Glycopolymers Combining RAFT Polymerization, Thiol‐Ene Reaction, and Subsequent Immobilization onto Solid Supports

Ehe

Weber

Wagner

et al. 2014

Macro Chemistry & Physics

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“…Multivalent sulfonated groups have been reported to interact with Aβ with GAGs [ 26 ], 6-sulfoGlcNAc polymer [ 14 , 15 ], sulfonated Glc polymer [ 27 ], and the polymer with sulfonic acid [ 28 ]. It is obvious that the sulfonic acid interact with Aβ via electrostatic interaction.…”

Section: Resultsmentioning

confidence: 99%

Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation

2012

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A series of novel glycol-clusters containing sulfonated N-acetyl-D-glucosamine (GlcNAc) have been synthesized using click chemistry. Three dendrimers with aromatic dendrons were synthesized using chlorination, azidation and click chemistries. The resulting dendrimers were modified with azide-terminated sulfonated GlcNAc using click chemistry. The sulfonated dendrimers showed affinity for proteins, including the lectin wheat germ agglutinin and amyloid beta peptide (1-42). The dendrimers of G1 and G2 in particular showed the largest affinity for the proteins. The addition of the sulfonated GlcNAc dendrimers of G1 and G2 exhibited an inhibition effect on the aggregation of the amyloid beta peptide, reduced the β-sheet conformation, and led to a reduction in the level of nanofiber formation.

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“…The majority of glycopolymer brushes reported the use of glucose derivatives as the saccharide unit, mainly due to glucose bioavailability, biocompatibility, and known recognition ability by different lectins, like Con A, Griffonia simplicifolia or wheat germ lectins [ 5 , 7 , 38 , 39 , 40 ]. Most of the glucose-based brushes are obtained by the direct polymerization of the glycomonomer, on its protected or unprotected form, by SI-ATRP from a functionalized surface, using water or alcohol/water mixtures as solvents, CuCl or CuBr as the catalyst and bipyridine as the ligand [ 17 , 41 , 42 , 43 , 44 ]. To the best of our knowledge, there is only one work reporting the preparation of glucosamine-containing brushes by RAFT polymerization from silicon wafer by the Z-group approach [ 30 ].…”

Section: Glucose-containing Polymer Brushesmentioning

confidence: 99%

Glycopolymer Brushes by Reversible Deactivation Radical Polymerization: Preparation, Applications, and Future Challenges

et al. 2020

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The cellular surface contains specific proteins, also known as lectins, that are carbohydrates receptors involved in different biological events, such as cell–cell adhesion, cell recognition and cell differentiation. The synthesis of well-defined polymers containing carbohydrate units, known as glycopolymers, by reversible deactivation radical polymerization (RDRP) methods allows the development of tailor-made materials with high affinity for lectins because of their multivalent interaction. These polymers are promising candidates for the biomedical field, namely as novel diagnostic disease markers, biosensors, or carriers for tumor-targeted therapy. Although linear glycopolymers are extensively studied for lectin recognition, branched glycopolymeric structures, such as polymer brushes can establish stronger interactions with lectins. This specific glycopolymer topology can be synthesized in a bottlebrush form or grafted to/from surfaces by using RDRP methods, allowing a precise control over molecular weight, grafting density, and brush thickness. Here, the preparation and application of glycopolymer brushes is critically discussed and future research directions on this topic are suggested.

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Binding of β-amyloid to sulfated sugar residues in a polymer brush

Cited by 11 publications

References 56 publications

Synthesis of Thermoresponsive Glycopolymers Combining RAFT Polymerization, Thiol‐Ene Reaction, and Subsequent Immobilization onto Solid Supports

Synthesis of Thermoresponsive Glycopolymers Combining RAFT Polymerization, Thiol‐Ene Reaction, and Subsequent Immobilization onto Solid Supports

Syntheses of Sulfo-Glycodendrimers Using Click Chemistry and Their Biological Evaluation

Glycopolymer Brushes by Reversible Deactivation Radical Polymerization: Preparation, Applications, and Future Challenges

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