九州大学 研究者情報
論文一覧
三浦 佳子(みうら よしこ) データ更新日:2024.04.25

教授 /  工学研究院 化学工学部門 工学府 化学システム工学専攻 生体界面工学 (分子・生物システム工学講座)


原著論文
1. Yoshiko Miura, Masanori Nagao, Hikaru Matsumoto, De Novo designed glycopolymer by the precise polymer synthesis, Chemistry Letters, https://doi.org/10.1093/chemle/upad012, 2023.12, Synthetic polymers with molecular recognition ability were investigated. Well-defined chemical structures of biopolymers were mimicked by controlled polymerization. In particular, the preparation and molecular recognition of de novo designed glycopolymers were studied. Glycopolymers such as block polymers, star polymers, and microgels were prepared. The designed glycopolymers showed strong molecular recognition against target proteins and viruses..
2. Masanori Nagao, Aya Horie, Hikaru Matsumoto, Yu Hoshino, Yoshiko Miura, Continuous-Flow PET-RAFT Polymerization in a Packed-Bed Reactor with Porphyrin-Immobilized Silica Particles, Industrial & Engineering Chemistry Research, doi.org/10.1021/acs.iecr.3c03496, 2023.12, Photoinduced electron/energy transfer-reversible addition–fragmentation chain transfer (PET-RAFT) polymerization enables the production of well-controlled synthetic polymers under mild conditions by using visible-light energy. Although flow reactors are suitable for photoreactions in terms of light penetration, contamination of photocatalysts occurs in a homogeneous system and necessitates product purification. Immobilizing the photocatalysts onto supports can eliminate the need for this purification step and enhance the potential for industrial applications of PET-RAFT polymerization. Herein, we report the development of a packed-bed flow photoreactor wherein a photocatalyst for PET-RAFT polymerization, zinc tetraphenylporphyrin, was immobilized onto packed silica particles. Continuous PET-RAFT polymerization of a model monomer (N,N-dimethylacrylamide) was achieved without leakage of the porphyrin molecules. The effects of various reaction conditions, such as the residence time, catalyst density, and target molecular weight, on the polymerization reaction were evaluated. This work contributes to the realization of a facile and practical manufacturing process for highly valuable synthetic polymers..
3. Hiroyuki Koide, Chiaki Kiyokawa, Anna Okishima, Kaito Saito, Keiichi Yoshimatsu, Tatsuya Fukuta, Yu Hoshino, Tomohiro Asai, Yuri Nishimura, Yoshiko Miura, Naoto Oku, Kenneth J. Shea, Design of an Anti-HMGB1 Synthetic Antibody for In Vivo Ischemic/Reperfusion Injury Therapy, Journal of the American Chemical Society, https://doi.org/10.1021/jacs.3c06799, 2023.10, High-mobility group box 1 (HMGB1) is a multifunctional protein. Upon injury or infection, HMGB1 is passively released from necrotic and activated dendritic cells and macrophages, where it functions as a cytokine, acting as a ligand for RAGE, a major receptor of innate immunity stimulating inflammation responses including the pathogenesis of cerebral ischemia/reperfusion (I/R) injury. Blocking the HMGB1/RAGE axis offers a therapeutic approach to treating these inflammatory conditions. Here, we describe a synthetic antibody (SA), a copolymer nanoparticle (NP) that binds HMGB1. A lightly cross-linked N-isopropylacrylamide (NIPAm) hydrogel copolymer with nanomolar affinity for HMGB1 was selected from a small library containing trisulfated 3,4,6S-GlcNAc and hydrophobic N-tert-butylacrylamide (TBAm) monomers. Competition binding experiments with heparin established that the dominant interaction between SA and HMGB1 occurs at the heparin-binding domain. In vitro studies established that anti-HMGB1-SA inhibits HMGB1-dependent ICAM-1 expression and ERK phosphorylation of HUVECs, confirming that SA binding to HMGB1 inhibits the proteins’ interaction with the RAGE receptor. Using temporary middle cerebral artery occlusion (t-MCAO) model rats, anti-HMGB1-SA was found to accumulate in the ischemic brain by crossing the blood–brain barrier. Significantly, administration of anti-HMGB1-SA to t-MCAO rats dramatically reduced brain damage caused by cerebral ischemia/reperfusion. These results establish that a statistical copolymer, selected from a small library of candidates synthesized using an “informed” selection of functional monomers, can yield a functional synthetic antibody. The knowledge gained from these experiments can facilitate the discovery, design, and development of a new category of drug..
4. Masanori Nagao, Hikaru Matsumoto, Yoshiko Miura , Design of Glycopolymers for Controlling the Interactions with Lectins, Chemistry – An Asian Journal, 10.1002/asia.202300643, 10.1002/asia.202300643, 2023.08, Carbohydrates are involved in life activities through the interactions with their corresponding proteins (lectins). Pathogen infection and the regulation of cell activity are controlled by the binding between lectins and glycoconjugates on cell surfaces. A deeper understanding of the interactions of glycoconjugates has led to the development of therapeutic and preventive methods for infectious diseases. Glycopolymer is one of the classes of the materials present multiple carbohydrates. The properties of glycopolymers can be tuned through the molecular design of the polymer structures. This review focuses on research over the past decade on the design of glycopolymers with the aim of developing inhibitors against pathogens and manipulator of cellular functions..
5. Hikaru Matsumoto, Yu Hoshino, Tomohiro Iwai, Masaya Sawamura, Yoshiko Miura, Sheltering Mono‐P‐Ligated Metal Complexes in Porous Polystyrene Monolith: Effect of Aryl Pendant Stabilizers on Catalytic Durability, Chemistry A European Journal, 10.1002/chem.202301847, 29, 55, e202301847, Chemistry A European Journal, 2023, 29, 55, e202301847, 2023.07, Metal centers that can generate coordinatively unsaturated metals in accessible and stable states have been developed using synthetic polymers with sophisticated ligand and scaffold designs, which required synthetic efforts. Herein, we report a simple and direct strategy for producing polymer-supported phosphine-metal complexes, which stabilizes mono-P-ligated metals by modulating the electronic properties of the aryl pendant groups in the polymer platform. A three-fold vinylated PPh3 was copolymerized with a styrene derivative and a cross-linker to produce a porous polystyrene-phosphine hybrid monolith. Based on the Hammett substituent constants, the electronic properties of styrene derivatives were modulated and incorporated into the polystyrene backbone to stabilize the mono-P-ligated Pd complex via Pd-arene interactions. Through NMR, TEM, and comparative catalytic studies, the polystyrene-phosphine hybrid, which induces selective mono-P-ligation and moderate Pd-arene interactions, demonstrated high catalytic durability for the cross-coupling of chloroarenes under continuous-flow conditions..
6. Masanori Nagao, Yoshiko Miura , Correlation between Self-Folding Behavior of Amphiphilic Polymers and Their Molecular Flexibility, ACS Macro Letters, 10.1021/acsmacrolett.3c00182, 12, 6, 733-737, ACS Macro Lett. 2023, 12, 6, 733–737, 2023.05, Self-folding behavior of amphiphilic polymers in aqueous environments mimics the structures of biomacromolecules (e.g., proteins). Since both the three-dimensional structure (static) and the molecular flexibility (dynamic) of a protein are essential for its biological functions, the latter should be considered when designing synthetic polymers that are intended to mimic proteins. Herein, we investigated the correlation between the self-folding behavior of amphiphilic polymers and their molecular flexibility. We synthesized amphiphilic polymers by subjecting N,N-dimethylacrylamide (hydrophilic) and N-benzylacrylamide (hydrophobic) to living radical polymerization. Polymers containing 10, 15, and 20 mol % of N-benzylacrylamide demonstrated self-folding behavior in an aqueous phase. The spin–spin relaxation time (T2) of the hydrophobic segments decreased with the percent collapse of the polymer molecules, indicating that mobility was restricted by the self-folding behavior. Furthermore, comparison of the polymers with random and block sequences revealed that the mobility of hydrophobic segments was not affected by the component of the local segments..
7. Masanori Nagao, Shuya Tanaka, Yoshiko Miura, Preparation of an amphipathic polymer library in a mixture of water/ethanol by photoinduced polymerization and evaluation of the cryoprotective activity, Materials Advances, 10.1039/D3MA00251A , 4, 3192-3196, 2023, 4, 3192-3196, 2023.04, [URL], Synthetic cryoprotectants with macromolecular structures are desirable as alternatives to commonly used ones. Herein, we prepared an amphipathic polymer library and evaluated the cryoprotective ability of the polymers by facile screening using red blood cells. The cryoprotective properties of the amphipathic polymers was independent of both the log[thin space (1/6-em)]P values of the hydrophobic groups and the ice recrystallization inhibition activity..
8. Masanori Nagao, Yu Hoshino, Yoshiko Miura, Synthesis of well-defined cyclic glycopolymers and the relationship between their physical properties and their interaction with lectins, Polymer Chemistry, 10.1039/d2py00941b, 13, 5453-5457, Polym. Chem., 2022, 13, 5453-5457, 2022.09.
9. Jiamin Cheng, Hikaru Matsumoto, Keita Shichijo, Yoshiko Miura, Hisashi Shimakoshi, Effect of Catalyst Support in B12-Based Heterogeneous Catalysts for Catalytic Alkane Oxidations, Bulletin of the Chemical Society of Japan, 10.1246/bcsj.20220161, 95, 8, 1250-1252, 2022, 95(8), 1250-1252, 2022.08.
10. Tomoki Imoto, Hikaru Matsumoto, Seiya Nonaka, Keita Shichijo, Masanori Nagao, Hisashi Shimakoshi, Yu Hoshino, Yoshiko Miura, 4-Amino-TEMPO-Immobilized Polymer Monolith: Preparations, and Recycling Performance of Catalyst for Alcohol Oxidation, Polymers, 10.3390/polym14235123, 14, 23, 5123, Polymers 2022, 14(23), 5123, 2022.11.
11. Yusuke Saito, Ryutaro Honda, Sotaro Akashi, Hinata Takimoto, Masanori Nagao, Yoshiko Miura, Yu Hoshino, Polymer Nanoparticles with Uniform Monomer Sequences for Sequence Specific Peptide Recognition, Angewandte Chemie, 10.1002/ange.202206456, 2022.05, [URL], Synthetic polymer nanoparticles (NPs) that recognize and neutralize target biomacromolecules are of considerable interest as “plastic antibodies”, synthetic mimics of antibodies. However, monomer sequences in the synthetic NPs are heterogeneous. The heterogeneity limits the target specificity and safety of the NPs. Herein, we report the synthesis of NPs with uniform monomer sequences for recognition and neutralization of target peptides. A multifunctional oligomer with a precise monomer sequence that recognizes the target peptide was prepared via cycles of reversible addition–fragmentation chain transfer (RAFT) polymerization and flash chromatography. The oligomer or blend of oligomers was used as a chain transfer agent and introduced into poly(N-isopropyl acrylamide) hydrogel NPs by radical polymerization. Evaluation of the interaction with the peptides revealed that multiple oligomers in NPs cooperatively recognized the sequence of the target peptide and neutralized its toxicity. Effect of sequence, combination, density and molecular weight distribution of precision oligomers on the affinity to the peptides was also investigated..
12. Masanori Nagao, Yuri Kimoto, Yu Hoshino, Yoshiko Miura, Facile Preparation of a Glycopolymer Library by PET-RAFT Polymerization for Screening the Polymer Structures of GM1 Mimics, ACS Omega, 10.1021/acsomega.2c00719, 7, 15, 13254-13259, ACS Omega 2022, 7, 15, 13254–13259, 2022.04, [URL], Commercialized oligosaccharides such as GM1 are useful for biological applications but generally expensive. Thus, facile access to an effective alternative is desired. Glycopolymers displaying both carbohydrate and hydrophobic units are promising materials as alternatives to oligosaccharides. Prediction of the appropriate polymer structure as an oligosaccharide mimic is difficult, and screening of the many candidates (glycopolymer library) is required. However, repeating polymerization manipulation for each polymer sample to prepare the glycopolymer library is time-consuming. Herein, we report a facile preparation of the glycopolymer library of GM1 mimics by photoinduced electron/energy transfer-reversible addition–fragmentation chain-transfer (PET-RAFT) polymerization. Glycopolymers displaying galactose units were synthesized in various ratios of hydrophobic acrylamide derivatives. The synthesized glycopolymers were immobilized on a gold surface, and the interactions with cholera toxin B subunits (CTB) were analyzed using surface plasmon resonance imaging (SPRI). The screening by SPRI revealed the correlation between the log P values of the hydrophobic monomers and the interactions of the glycopolymers with CTB, and the appropriate polymer structure as a GM1 mimic was determined. The combination of the one-time preparation and the fast screening of the glycopolymer library provides a new strategy to access the synthetic materials for critical biomolecular recognition..
13. M Nagao, A Yamaguchi, T Matsubara, Y Hoshino, T Sato, Y Miura, De Novo Design of Star-Shaped Glycoligands with Synthetic Polymer Structurestoward an Influenza Hemagglutinin Inhibitor, Biomacromolecules, 10.1021/acs.biomac.1c01483, 23, 3, 1232-1241, Biomacromolecules 2022, 23, 3, 1232–1241, 2021.12, Synthetic polymers with well-defined structures allow the development of nanomaterials with additional functions beyond biopolymers. Herein, we demonstrate de novo design of star-shaped glycoligands to interact with hemagglutinin (HA) using well-defined synthetic polymers with the aim of developing an effective inhibitor for the influenza virus. Prior to the synthesis, the length of the star polymer chains was predicted using the Gaussian model of synthetic polymers, and the degree of polymerization required to achieve multivalent binding to three carbohydrate recognition domains (CRDs) of HA was estimated. The star polymer with the predicted degree of polymerization was synthesized by reversible addition–fragmentation chain transfer (RAFT) polymerization, and 6′-sialyllactose was conjugated as the glycoepitope for HA. The designed glycoligand exhibited the strongest interaction with HA as a result of multivalent binding. This finding demonstrated that the biological function of the synthetic polymer could be controlled by precisely defining the polymer structures..
14. T Oh , T Uemura, M Nagao, Y Hoshino, Y Miura, A QCM study of strong carbohydrate–carbohydrate interactions of glycopolymerscarrying mannosides on substrates, Journal of Materials Chemistry B, 10.1039/D1TB02344F, 10, 2597-2601, J. Mater. Chem. B, 2022, 10, 2597-2601 10.1039/D1TB02344F (Paper), 2021.12, [URL], Carbohydrates on cell surfaces are known to interact not only with lectins but also with other carbohydrates; the latter process is known as a carbohydrate–carbohydrate interaction. Such interactions are observed in complex oligosaccharides. It would be surprising if these interactions were observed in simple monosaccharides of mannose. In this study, the interaction between glycopolymers carrying monosaccharides of mannose was quantitatively investigated by quartz crystal microbalance measurements. We measured the interactions with glycopolymers carrying mannose, galactose and glucose. Surprisingly, the interaction between the glycopolymers and mannose was much stronger than that between other saccharides..
15. T Ishida , M Nagao, T Oh, T Mori, Y Hoshino, Y Miura, Synthesis of Glycopolymers Carrying 3’-Sialyllactose for Suppressing InflammatoryReaction via Siglec-E, Chemistry Letters, 51, 3, 308-311, Chem. Lett. 2022, 51, 308–311 | doi:10.1246/cl.210740, 2021.12, [URL], One of the new strategies to treat autoimmune diseases is to target Siglec, a membrane protein receptor with the ability to suppress immune responses. Herein, we synthesized glycopolymers carrying 3′-sialyllactose in various glycounit densities. RAW 264.7 macrophages transfected to express secreted alkaline phosphatase (SEAP) were used to evaluate the immunosuppression ability of the glycopolymers. The inhibition of the signal transmission was dependent on the glycounit densities of the glycopolymers, and was maximized at the moderate density (70%)..
16. S Nonaka, H Matsumoto, M Nagao, Y Hoshino, Y Miura, Investigation of the effect of microflow reactor diameter on condensationreactions in l-proline-immobilized polymer monoliths, Reaction Chemistry & Engineering, 10.1039/D1RE00386K, 7, 1, 55-60, 10.1039/D1RE00386K (Communication) React. Chem. Eng., 2022, 7, 55-60, 2021.11, [URL], The effect of monolith structure and monolith reactor inner diameter on the residence time distribution (RTD), and the relationship between RTD and the catalytic efficiency of the asymmetric aldol addition reaction between p-nitrobenzaldehyde and cyclohexanone were examined. A monolith column containing L-proline as a catalyst was prepared using poly(ethylene glycol) (PEG) as the porogen. The monolith column prepared with PEG with a molecular weight of 6000 Da displayed a narrow pore size distribution and showed a controlled RTD. The performance of monolith reactors with different inner diameters (micro- and millireactors, 0.53 and 4.00 mm) was compared: the microreactor displayed a narrower RTD and a higher turnover number for the asymmetric aldol addition reaction than the millireactor. The different linear flow velocities in the microreactor did not affect the catalytic reaction efficiency and enantioselectivity, demonstrating that the RTDs can be controlled regardless of the flow velocity..
17. Benshuai Guo, Yoshiko Miura, Yu Hoshino, Rational Design of Thermocells Driven by the Volume Phase Transition of Hydrogel Nanoparticles, ACS Applied Materials & Interfaces, 10.1021/acsami.1c07266, 13, 27, 32184-32192, ACS Appl. Mater. Interfaces 2021, 13, 27, 32184–32192, 2021.10, Thermocells are thermoelectrochemical conversion systems for harvesting low-temperature thermal energy. Liquid-state thermocells are particularly desirable because of low cost and their high conversion efficiency at temperatures around physiological temperature, and they have, thus, been extensively studied. However, the performance of the thermocells has to be improved to utilize them as energy chargers and/or batteries. Recently, we reported that a liquid-state thermocell driven by the volume phase transition of hydrogel nanoparticles showed highly efficient thermoelectric conversion with Seebeck coefficient (Se) of −6.7 mV K–1. Here, we report the design rationale of the thermocells driven by the phase transition. A high Se of −9.5 mV K–1 was achieved at temperature between 36 and 40 °C by optimizing choice and amount of redox chemical species. The figure of merit (ZT) of the thermocell was improved by selecting appropriate electrolyte salt to increase the ionic conductivity and prevent the precipitation of nanoparticles. Furthermore, screening of nanoparticles revealed the high correlation between Se and the pH shift generated as a result of phase transition of the nanoparticles. After optimization, the maximum ZT of 8.0 × 10–2 was achieved at a temperature between 20 and 70 °C..
18. Masanori Nagao, Takeshi Uemura, Tasuku Horiuchi, Yu Hoshino, , Screening of a glycopolymer library for GM1 mimetics synthesized by the “carbohydrate module method”, Chemical Communications, 10.1039/D1CC04394C, 57, 10871-10874, Chem. Commun., 2021, 57, 10871-10874, 2021.09, The “carbohydrate module method” is a promising approach for oligosaccharide mimetics using polymeric materials. However, it is difficult to predict the optimal structure for a particular oligosaccharide mimetic, and an efficient strategy for the synthesis and evaluation of glycopolymers is desirable. In this study, a screening of glycopolymers for the “carbohydrate module method” by a combination of photoinduced electron/energy transfer-reversible addition–fragmentation chain-transfer (PET-RAFT) polymerization and surface plasmon resonance imaging (SPRI) is demonstrated. The facile and fast screening of synthetic glycomimetics was achieved, and the glycopolymer with the optimal structure as a GM1 mimetic strongly interacted with the cholera toxin B subunit..
19. Seiji KAMBA, Atsushi OGURA, Yoshiko MIURA, Makoto HASEGAWA, Enrichment of Uncommon Bacteria in Soil by Fractionation Using a Metal Mesh Device, Analytical Science, 10.2116/analsci.21P042, 9, 1295-1300, Anal Sci Vol. 37 (2021), No. 9 pp. 1295-1300, 2021.09.
20. Hirokazu Seto, Atsushi Saikia, Ryosuke Matsushita, Wataru Mitsukami, Seiji Kamba, Makoto Hasegawa,Yoshiko Miura, Yumiko Hirohashi, Hiroyuki Shinto, Development of microparticle counting sensor based on structural and spectroscopic properties of metal mesh device, Advanced Powder Technology
Volume 32, Issue 6, June 2021, Pages 1920-1926
, 10.1016/j.apt.2021.04.002, 32, 6, 1920-1926, 2021,32(6),1920-1926, 2021.06, A microparticle counter based on a metal mesh device was developed. The metal mesh device had a lattice-shaped structure with well-regulated holes of 1.8 μm. The collection percentages of differently sized microparticles using the metal mesh device were determined by flow cytometry. The cut-off point and hole size of the metal mesh device were identical. Polystyrene microparticles were detected from changes in the spectroscopic properties of the metal mesh device. When microparticles were trapped on the holes of the metal mesh device, the transmittance in the infrared spectra decreased. Microparticles smaller than the holes were not detected by the metal mesh device, whereas 2 and 3 μm microparticles were detected. Polystyrene and silica microparticles could be counted using the metal mesh device via calibration curves between the concentration of microparticles and the change level in the transmittance of the metal mesh device. The separation of microparticles from a mixture suspension using the metal mesh device was evaluated. Unlike a microfiber filter, only 2 μm microparticles were collected from coexisting 1 μm microparticles by the metal mesh device. Owing to its high separation ability, the metal mesh device selectively detected 2 μm microparticles in coexisting 10-equivalence 1 μm microparticles..
21. Masanori Nagao, Masaya Kichize, Yu Hoshino, Yoshiko Miura, Influence of Monomer Structures for Polymeric Multivalent Ligands: Consideration of the Molecular Mobility of Glycopolymers, Biomacromolecules, 10.1021/acs.biomac.1c00553, 22, 7, 3119-3127, Biomacromolecules 2021, 22, 7, 3119–3127, 2021.06, Molecular mobility is important for interactions of biofunctional polymers with target molecules. Monomer structures for synthetic biofunctional polymers are usually selected based on their compatibility with polymerization systems, whereas the influence of monomer structures on the interaction with target molecules is hardly considered. In this report, we evaluate the correlation between the monomer structures of glycopolymers and their interactions with concanavalin A (ConA) with respect to the molecular mobility. Two types of glycopolymers bearing mannose are synthesized with acrylamide or acrylate monomers. Despite the similar structures, except for amide or ester bonds in the side chains, the acrylate-type glycopolymers exhibit stronger interaction with ConA both in the isothermal titration calorimetry measurement and in a hemagglutination inhibition assay. Characterization of the acrylate-type glycopolymers suggests that the higher binding constant arises from the higher molecular mobility of mannose units, which results from the rotational freedom of ester bonds in their side chains..
22. Yu Hoshino, Tomohiro Gyobu, Kazushi Imamura, Akira Hamasaki, Ryutaro Honda, Ryoga Horii, Chie Yamashita, Yuki Terayama, Takeshi Watanabe, Shoma Aki, Yida Liu, Junko Matsuda, Yoshiko Miura, Ikuo Taniguchi, Assembly of Defect-Free Microgel Nanomembranes for CO2 Separation, ACS Appl. Mater. Interfaces , 10.1021/acsami.1c06447, 13, 25, 30030-30038, ACS Appl. Mater. Interfaces 2021, 13, 25, 30030–30038, 2021.06, The development of robust and thin CO2 separation membranes that allow fast and selective permeation of CO2 will be crucial for rebalancing the global carbon cycle. Hydrogels are attractive membrane materials because of their tunable chemical properties and exceptionally high diffusion coefficients for solutes. However, their fragility prevents the fabrication of thin defect-free membranes suitable for gas separation. Here, we report the assembly of defect-free hydrogel nanomembranes for CO2 separation. Such membranes can be prepared by coating an aqueous suspension of colloidal hydrogel microparticles (microgels) onto a flat, rough, or micropatterned porous support as long as the pores are hydrophilic and the pore size is smaller than the diameter of the microgels. The deformability of the microgel particles enables the autonomous assembly of defect-free 30–50 nm-thick membrane layers from deformed ∼15 nm-thick discoidal particles. Microscopic analysis established that the penetration of water into the pores driven by capillary force assists the assembly of a defect-free dense hydrogel layer on the pores. Although the dried films did not show significant CO2 permeance even in the presence of amine groups, the permeance dramatically increased when the membranes are adequately hydrated to form a hydrogel. This result indicated the importance of free water in the membranes to achieve fast diffusion of bicarbonate ions. The hydrogel nanomembranes consisting of amine-containing microgel particles show selective CO2 permeation (850 GPU, αCO2/N2 = 25) against post-combustion gases. Acid-containing microgel membranes doped with amines show highly selective CO2 permeation against post-combustion gases (1010 GPU, αCO2/N2 = 216) and direct air capture (1270 GPU, αCO2/N2 = 2380). The membrane formation mechanism reported in this paper will provide insights into the self-assembly of soft matters. Furthermore, the versatile strategy of fabricating hydrogel nanomembranes by the autonomous assembly of deformable microgels will enable the large-scale manufacturing of high-performance separation membranes, allowing low-cost carbon capture from post-combustion gases and atmospheric air..
23. Hirokazu Seto, Atsushi Saiki, Ryosuke Matsushita, Wataru Mitsukami, Seiji Kamba, Makoto Hasegawa, Yoshiko Miura, Yumiko Hirohashi, HiroyukiShinto, Development of microparticle counting sensor based on structural and spectroscopic properties of metal mesh device, Advanced Powder Technology, doi.org/10.1016/j.apt.2021.04.002, 32, 6, 1920-1926, 2021, 32(6),1920-1626, 2021.04, A microparticle counter based on a metal mesh device was developed. The metal mesh device had a lattice-shaped structure with well-regulated holes of 1.8 μm. The collection percentages of differently sized microparticles using the metal mesh device were determined by flow cytometry. The cut-off point and hole size of the metal mesh device were identical. Polystyrene microparticles were detected from changes in the spectroscopic properties of the metal mesh device. When microparticles were trapped on the holes of the metal mesh device, the transmittance in the infrared spectra decreased. Microparticles smaller than the holes were not detected by the metal mesh device, whereas 2 and 3 μm microparticles were detected. Polystyrene and silica microparticles could be counted using the metal mesh device via calibration curves between the concentration of microparticles and the change level in the transmittance of the metal mesh device. The separation of microparticles from a mixture suspension using the metal mesh device was evaluated. Unlike a microfiber filter, only 2 μm microparticles were collected from coexisting 1 μm microparticles by the metal mesh device. Owing to its high separation ability, the metal mesh device selectively detected 2 μm microparticles in coexisting 10-equivalence 1 μm microparticles..
24. Yoshiko MIURA, Yuki KOJIMA, Hirokazu SETO, Yu HOSHINO, Bio-inert Properties of TEG Modified Dendrimer Interface, Analytical Sciences, 10.2116/analsci.20P388, 37, 3, 519-523, 2021,37(3), 519-523, 2021.03, The bioinert interfaces that prevent adhesion of proteins and cells are important for biomaterial applications. In order to design a bioinert interface, the immobilization of an appropriate functional group and the control of molecular density is required. Dendrimer was modified with triethylene glycol (TEG) to display a dense brush structure. TEG with different density and terminal groups were immobilized with a dendrimer template and thiol terminated molecules. The inhibitory effect on protein and bacteria binding was investigated. The physical property of the interface was measured by QCM-admittance to clarify the factor of the bioinert property..
25. Masaya Kichize, Masanori Nagao, Yu Hoshino, Yoshiko Miura, Multi-block and sequence-controlled polymerization of glycopolymers, andinteraction with lectin, European Polymer Journal, doi.org/10.1016/j.eurpolymj.2020.110044, 140, 110044, 2020.11.
26. Takahiro Oh, Yu Hoshino, Yoshiko Miura,, Aggregation of a double hydrophilic block glycopolymer: the effect ofblock polymer ratio, Journal of Materials Chemistry B, doi.org/10.1039/DoTB02093A, 8, 10101-10107, 2020.10.
27. Benshuai Guo, Yu Hoshino, Fan Gao, Keisuke HayashiYoshiko Miura, Nobuo Kimizuka, Teppei Yamada, Thermocells driven by phase transition of hydrogel nanoparticles, J.Am.Chem.Soc, doi.org/10.1021/jacs.0c08600, 142, 41, 17318-17322, 2020, 142, 41, 17318–17322, 2020.09.
28. Ryutaro Honda, Akira Hamasaki, Yoshiko Miura, Yu Hoshino, Thermoresponsive CO2 absorbent for various CO2 concentrations: tuning the pKa of ammonium ions for effective carbon capture, Polymer Journal volume, 10.1038/s41428-020-00407-5, 53, 157-167, 2021, 53, 157-167, 2020.09.
29. Hikaru Matsumoto, Yu Hoshino, Tomohiro Iwai, Masaya Sawamura, Yoshiko Miura, Polystyrene‐Supported PPh3 in Monolithic Porous Material: Effect of Cross‐Linking Degree on Coordination Mode and Catalytic Activity in Pd‐Catalyzed C−C Cross‐Coupling of Aryl Chlorides, ChemCatChem, doi.org/10.1002/cctc.202000651, 12, 16, 4034-4037, 2020.08, Hybridization of porous synthetic polymer and sophisticated ligands play an important role in transition‐metal catalysis for chemical transformations at laboratory and industrial levels. A monolithic porous polymer, which is a single piece with continuous macropores, is desired for high permeability, fast mass transfer properties, high stability, and easy modification. Herein, we first develop a monolithic porous polystyrene containing three‐fold cross‐linked PPh3 (M‐PS‐TPP ) for transition‐metal catalysis. The monolithic and macroporous structure of M‐PS‐TPP was fabricated via polymerization‐induced phase separation using porogenic solvent. Moreover, the M‐PS‐TPP was synthesized using different feed ratios of divinylbenzene (DVB) for site‐isolation and mono‐P‐ligating behavior of PPh3. 31P CP/MAS NMR analysis revealed that the different selectivity of M‐PS‐TPP s was obtained in formation of mono‐P‐ligation toward PdII. The macroporous properties and controlled mono‐P‐ligating behavior of M‐PS‐TPP facilitated the challenging Pd‐catalyzed Suzuki‐Miyaura cross‐coupling reaction of chloroarenes..
30. Yu Hoshino,Shinnosuke Shimohara,Yusuke Wada,Masahiko Nakamoto, Yoshiko Miura , Affinity Purification of Multifunctional Oligomeric Ligands Synthesized via Controlled Radical Polymerization, Journal of Materials Chemistry B, doi.org/10.1039/d0tb00849d, 8, 5597-5601, 2020.07.
31. Hikaru Matsumoto, Yu Hoshino, Tomohiro Iwai, Masaya Sawamura, Yoshiko Miura, Polystyrene-Cross-Linking Triphenylphosphine on a Porous Monolith: EnhancedCatalytic Activity for Aryl Chloride Cross-Coupling in Biphasic Flow, Ind.Eng. Chem., doi.org/10.1021/acs.iecr.0c02404, 59, 34, 15179-15187, 2020,59, 34, 15179-15187., 2020.07.
32. Ryutaro Honda, Tomohiro Gyobu, Hideto Shimahara, Yoshiko Miura, Yu Hoshino*, Electrostatic Interactions between Acid-/Base-Containing Polymer Nanoparticles and Proteins: Impact of Polymerization pH, ACS Appl. Bio Mater., 10.1021/acsabm.0c00390, 3, 6, 3827-3834, 2020,3, 6, 3827-3834., 2020.06, Electrostatic interaction between synthetic polymer nanoparticles (NPs) and proteins is of considerable importance in the design of NPs that capture, neutralize, and deliver target molecules in a biological milieu. Ionizable functional groups, such as carboxylic acids and amines, are often introduced to NPs to tune the affinity with target bio-macromolecules through electrostatic attraction and repulsion. However, acids/bases are not always ionized at a physiological pH because acidities of the functional groups depend on the microenvironment around the acids/bases that are imprinted during the polymerization process. Here, we show that electrostatic interaction between acid-/base-containing NPs and target proteins strongly depends on the pH of the solution during the NP polymerization process. To prepare NPs that capture target proteins by electrostatic interactions at physiological pH, NPs must be polymerized within a pH range where the acid/base monomer is ionized. Acid-/base-containing NPs that exhibit completely different interactions with the proteins can be prepared by changing the polymerization pH without changing monomer compositions. Our results indicate that polymerization pH should be carefully tuned to design acid-/base-containing NPs that show desired affinity to all proteins in a biological milieu and to proteins of interest..
33. Hinata Takimoto, Sho Katakami, Yoshiko Miura, Yu Hoshino, Controlling the block sequence of multi-block oligomer ligands for neutralizationof a target peptide, Materials Advances, doi.org/10.1039/DoMA00149J, 1, 604-608, 2020, 1, 604-608., 2020.06.
34. Yida Liu, Takashi Kodama, Taisuke Kojima, Ikuo Taniguchi, Hirokazu Seto, Yoshiko Miura, YuHoshino, Fine-tuning of the surface porosity of micropatterned polyethersulfonemembranes prepared by phase separation micromolding, Polymer Journal, doi/10.1038/s41428-019-0298-9, 2020.04.
35. Yusuke Yoanmine, Kotaro Hiramatsu, Takuro Ideguchi, Takuro Ito, Tomomi Fujiwara, Yoshiko Miura, Keisuke Goda, Yu Hoshino, Spatiotemporal monitoring of intracellular metabolic dynamics by resonance Raman microscopy with isotope labeling, RSC Adv, 10.1039/D0RA02803G, 10, 16679-16686, 2020, 10, 16679-16686., 2020.04.
36. Yoshiko Miura, Controlled polymerization for the development of bioconjugate polymers and material, Journal of Materials Chemistry B, 10.1039/c9tb02418b, 8, 10, 2010-2019, 2020.03, [URL], Controlled polymerization through living radical polymerization is widely studied. Controlled polymerization enables synthetic polymers with precise structures, which have the potential for excellent bio-functional materials. This review summarizes the applications of controlled polymers, especially those via living radical polymerization, to biofunctional materials and conjugation with biomolecules. In the case of polymer ligands like glycopolymers, the polymers control the interactions with proteins and cells based on the precise polymer structures. Living radical polymerization enables the conjugation of polymers to proteins, antibodies, nucleic acids and cells. Those polymer conjugations are a sophisticated method to modify bio-organisms. The polymer conjugations expand the potential of biofunctional materials and are useful for understanding biology..
37. 服部 春香, 松本 光, 星野 友, 三浦 佳子, 有機分子触媒L-prolineを固定化した多孔質高分子モノリスの開発およびフロー不斉アルドール付加反応への応用, 化学工学論文集, doi.org/10.1252/kakoronbunshu.46.77, 46, 3, 77-83, 2020,46, 3, 77-83, 2020.03, フロー合成による化学合成プロセスが精密有機合成の分野で注目されている.実用的かつ高効率なフロー合成を実現するため,洗練されたフローシステムおよびよく設計された固定化触媒は強力な手段である.多孔質モノリスは,三次元的な貫通孔をもち大きな比表面積および高い透過性能を有する一塊の多孔質体である.本研究では,O-Acryloyl-trans-4-hydroxy-L-proline hydrochlorideを共重合したAcrylamide骨格の多孔質モノリスを作製し,その多孔性を評価した.また,作製したモノリスを不斉アルドール付加反応に応用し,その触媒活性について評価した.モノリスは,ポロゲンとして用いるアルコール(Ethanol, 1-Butanol, 1-Octanol, あるいは1-Dodecanol)により多孔質モノリスの細孔直径および比表面積を制御することができた.また,そのモノリスを用いてフローシステムを構築し,12 hの滞留時間においてフロー条件下で不斉アルドール付加反応を行った.すべてのモノリスは61–74%のeeでフロー不斉アルドール付加反応を達成した.これは,有機分子触媒L-Prolineを導入した多孔質高分子モノリスを用いて,フロー不斉合成を達成した初めての例である.
38. Seiji Kamba, Atsushi Ogura, Yoshiko Miura, Makoto Hasegawa, Enrichment of Uncommon Bacteria in Soil by Fractionation Using a Metal Mesh Device, Analytical Sciences, 10.2116/analsci.21P042, 2020.03.
39. Yu Hoshino, Shohei Taniguchi, Hinata Takimoto, Sotaro Akashi, Sho Katakami, Yusuke Yonamine, Yoshiko Miura, Homogeneous Oligomeric Ligands Prepared via Radical Polymerization that Recognize and Neutralize a Target Peptide, Angewandte Chemie - International Edition, 10.1002/anie.201910558, 59, 2, 679-683, 2020, 132,2,689-693., 2020.01, [URL], Abiotic ligands that bind to specific biomolecules have attracted attention as substitutes for biomolecular ligands, such as antibodies and aptamers. Radical polymerization enables the production of robust polymeric ligands from inexpensive functional monomers. However, little has been reported about the production of monodispersed polymeric ligands. Herein, we present homogeneous ligands prepared via radical polymerization that recognize epitope sequences on a target peptide and neutralize the toxicity of the peptide. Taking advantage of controlled radical polymerization and separation, a library of multifunctional oligomers with discrete numbers of functional groups was prepared. Affinity screening revealed that the sequence specificity of the oligomer ligands strongly depended on the number of functional groups. The process reported here will become a general step for the development of abiotic ligands that recognize specific peptide sequences..
40. Hirokazu Seto, Hikaru Matsumoto, Yoshiko Miura, Preparation of palladium-loaded polymer hydrogel catalysts with high durability and recyclability, Polymer Journal, 10.1038/s41428-020-0323-z, 52, 671-679, 2020, 52, 671-679., 2020.01, [URL], To establish effective chemical transformations, catalytic systems with advantages such as high activity, recyclability, durability, and operability have attracted considerable attention. One of the strategies for the development of high-performance catalytic systems is the use of polymer hydrogels. In this focus review, an overview of our research using poly(N-isopropyl acrylamide)-based hydrogel particles and macroporous monoliths as molecular catalysts and loading matrices for palladium catalysts is summarized..
41. Xiaojing Feng, Devendra S. Maurya, Nabil Bensabeh, Adrian Moreno, Takahiro Oh, Yuqing Luo, Jā Nis Lejnieks, Marina Galià,Yoshiko Miura, Michael J. Monteiro, Gerard Lligadas, Virgil Percec, Replacing Cu(II)Br2 with Me6-TREN in Biphasic Cu(0)/TREN Catalyzed SET-LRP Reveals the Mixed-Ligand Effect, Biomacromolecules, 10.1021/acs.biomac.9b01282, 21, 1, 250-261, 2020,21,1,250-261, 2020.01, [URL], The mixed-ligand system consisting of tris(2-aminoethyl)amine (TREN) and tris(2-dimethylaminoethyl)amine (Me6-TREN) during the Cu(0) wire-catalyzed single electron transfer-living radical polymerization (SET-LRP) of methyl acrylate (MA) in "programmed" biphasic mixtures of the dipolar aprotic solvents NMP, DMF, and DMAc with H2O is reported. Kinetic and chain end analysis studies by NMR and MALDI-TOF before and after thio-bromo "click" reaction demonstrated that Me6-TREN complements and makes the less expensive TREN a very efficient ligand in the absence of externally added Cu(II)Br2. Statistical analysis of the kinetic data together with control experiments demonstrated that this mixed-ligand effect enhanced the apparent rate constant of propagation, monomer conversion, and molecular weight control. The most efficient effect was observed at a 1/1 molar ratio between these two ligands, suggesting that in addition to a fast exchange between the two ligands, a new single dynamic ligand generated by hydrogen bonding may be responsible for the mixed ligand observed..
42. Yu Hoshino, Mitunori Moribe, Naoki Gondo, Toshiki Jibiki, Masahiko Nakamoto, Benshuai Guo, Rinoka Adachi, Yoshiko Miura, Combining Acid- and Base-Imprinted Nanoparticles in a Hydrogel Film forTemperature-Responsive Quick and Reversible Capture of Salt, ACS Appl. Polym. Mater, doi/10.1021/acsapm.9b00940, 2, 2, 505-514, 2020,2,2,505-514, 2019.12, [URL].
43. Yida Liu, Takashi Kodama, Taisuke Kojima, Ikuo Taniguchi, Hirokazu Seto, Yoshiko Miura, Yu Hoshino, Fine-tuning of the surface porosity of micropatterned polyethersulfone membranes prepared by phase separation micromolding, Polymer Journal , doi.org/10.1038/s41428-019-0298-9, 52, 397-403, Polymer Journal (2020) 52:397–403, 2019.12, Phase separation micromolding (PSμM) is an effective technique for fabricating porous membranes with micropatterned structures. However, reports on procedures to control the size and number of open pores on the patterned surface are scarce, which often limits the use of the surface-patterned membranes. This work presents a systematic study on tailoring open pores on the patterned surface of polyethersulfone (PES) membranes prepared by the PSμM procedure. The composition of the solvent and the concentration of PES in the casting solution were optimized to tune the size and number of pores on the membrane surfaces formed on a flat substrate during the nonsolvent-induced phase separation (NIPS) process. The surface porosity changed significantly and macrovoids appeared when the flat substrate was replaced by a micropatterned substrate. The vapor-induced phase separation process was applied prior to the NIPS process to prevent the formation of macrovoids. The composition of the casting solution was tuned again to prepare micropatterned porous PES membranes with open pores on the patterned surface. We observed that the size and number of pores were different depending on the pore locations on the patterned surface, which was caused by different solvent/nonsolvent demixing dynamics resulting from the physical discontinuity of micro-patterned membranes..
44. Yuri Kimoto, Yuhei Terada, Yu Hoshino, Yoshiko Miura, Screening of a Glycopolymer Library of GM1 Mimics Containing Hydrophobic Units Using Surface Plasmon Resonance Imaging, ACS Omega, 10.1021/acsomega.9b02877, 4, 24, 20690-20696, 2019, 4, 24, 20690-20696., 2019.11, [URL], Effective screening methods for the development of glycopolymers as molecular recognition materials are desirable for the discovery of novel biofunctional materials. A glycopolymer library was prepared to obtain guidelines for the design of glycopolymers for the recognition of cholera toxin B subunits (CTB). Glycopolymers with varying ratios of hydrophobic and sugar units were synthesized by reversible addition fragmentation chain transfer polymerization. N-tert-Butylacrylamide, N-phenylacrylamide, and N-cyclohexylacrylamide as hydrophobic units were copolymerized in the polymer backbone, and galactose, which contributes to CTB recognition, was introduced into the side chains by "post-click" chemistry. The thiol-terminated glycopolymers were immobilized on a gold surface. The polymer immobilization substrate was analyzed in terms of interaction with galactose recognition proteins (CTB, peanut agglutinin, and Ricinus communis agglutinin I) using surface plasmon resonance imaging. The polymers with high ratios of sugar and hydrophobic units had the strongest interactions with the CTB, which was different from the trend with peanut agglutinin and Ricinus communis agglutinin I. The binding constant of the CTB with the glycopolymer with hydrophobic units was 4.1 × 106 M-1, which was approximately eight times larger than that of the polymer without hydrophobic units. A correlation was observed between the log P value and the binding constant, indicating that the hydrophobic interaction played an important role in binding. New guidelines for the design of recognition materials were obtained by our screening method..
45. Takahiro Oh, Kazuki Jono, Yuri Kimoto, Yu Hoshino, Yoshiko Miura, Preparation of multifunctional glycopolymers using double orthogonal reactions and the effect of electrostatic groups on the glycopolymer–lectin interaction, Polymer Journal, 10.1038/s41428-019-0244-x, 51, 12, 1299-1308, 2019, 51,12,1299-1308, 2019.08, [URL], We investigated synthetic biomacromolecules to control molecular interactions. Multifunctional glycopolymers for molecular recognition were prepared via living radical polymerization and post-click chemistry with orthogonal Huisgen and thiol-epoxy reactions. The synthesis of the polymer backbone and the subsequent side-chain introduction successfully proceeded in high yield. The multifunctional glycopolymers had a tri-block structure: the first and third blocks contained mannose, and the second block contained either a positively or negatively charged group or a neutral hydrophilic group. The molecular recognition of the glycopolymers toward lectin was evaluated via fluorescence quenching measurements. Because of the electrostatic interaction, the binding constant varied in the following order: positively charged glycopolymer (PT110) > negatively charged glycopolymer (NT110). The effect of the electrostatic interactions was modest compared with the effect of the carbohydrate–lectin binding. These results suggested that the carbohydrate–lectin interaction was an important factor in the molecular recognition of glycopolymers. This study provides guidelines for the preparation of multifunctional polymers, such as biomaterials..
46. Kenneth J. Shea, @Hiroyuki Koide, Yoshiko Miura, Yu Hoshino, Yuri Nishimura, Naoto Oku, Abiotic Anti-VEGF Nanoparticle, United States Patent Application, 2019.07, The present invention relates generally to compositions and methods comprising abiotic, synthetic polymers with affinity and specificity to proteins. The synthetic polymers are an improvement over biological agents by providing a simpler, less expensive, and customizable platform for binding to proteins. In one embodiment, the compositions and methods relate to synthetic polymers with affinity and specificity to vascular endothelial growth factor (VEGF). In one embodiment, the compositions are useful for treating diseases and disorders related to the overexpression of VEGF. In one embodiment, the compositions are useful for treating cancer. In one embodiment, the compositions are useful for detecting VEGF levels from biological samples. In one embodiment, the compositions are useful for detecting overexpression of VEGF from biological samples. In one embodiment, the compositions are used to diagnose cancer..
47. Nagao,M., Matsubara, T., Hoshino, Y., Sato, T., Miura, Y., Synthesis of Various Glycopolymers Bearing Sialyllactose and the Effectof Their Molecular Mobility on Interaction with the Influenza Virus, Biomacromolecules, doi/10.1021/acs.biomac.9b00515, 20, 7, 2763-2769, 2019, 20, 7, 2763-2769, 2019.06.
48. Tomohiro Fukuda, Tsuji S, Yoshiko Miura, Glycopolymer preparation via post-polymerization modification using N-succinimidyl monomers, Polymer Journal, 10.1038/s41428-019-0170-y, 2019.05.
49. Seto, H.,Saiki, A.; Kamba, S.; Kondo, T.; Hasegawa, M.; Miura, Y.; Hhirohashi, Y.; hinto, H., Amplification of Sensor Signals from Metal Mesh Device with Fine Periodic Structure, Analytical Science, 10.2116/analsci.18P498, 35, 6, 619-623, 2019.05.
50. cui xinnan, Yu Hoshino, Yoshiko Miura, Fibronectin coating on implant material surface attracted both osteoblasts and bacteria, Chemistry Letters, doi.org/10.1246/cl.190293, 48, 8, 764-767, 2019, 48, 764-767, 2019.05.
51. Yoshiko Miura, Hirokazu Seto, Makoto Shibuya, Yu Hoshino, Biopolymer monolith for protein separation, Faraday Discussion, doi.org/10.1039/C9FD00018F, 219, 154-164, 2019, 219, 154-167, 2019.05.
52. Masanori Nagao, Teruhiko Matsubara, Yu Hoshino, Toshinori Sato, and Yoshiko Miura, Topological Design of Star Glycopolymers for Controlling the Interaction with the Influenza Virus, Bioconjugate Chemistry, 10.1021/acs.bioconjchem.9b00134, 30, 1192-1198, Bioconjugate Chemistry 2019,30,1192-1198, 2019.04, The precise design of synthetic polymer ligands using controlled polymerization techniques provides an advantage for the field of nanoscience. We report the topological design of glyco-ligands based on synthetic polymers for targeting hemagglutinin (HA, lectin on the influenza virus). To achieve precise arrangement of the glycounits toward the sugar-binding pockets of HA, triarm star glycopolymers were synthesized. The interaction of the star glycopolymers with HA was found to depend on the length of the polymer arms and was maximized when the hydrodynamic diameter of the star glycopolymer was comparable to the distance between the sugar-binding pockets of HA. Following the formula of multivalent interaction, the number of binding sites in the interaction of the glycopolymers with HA was estimated as 1.8–2.7. Considering one HA molecule has three sugar-binding pockets, these values were reasonable. The binding mode of synthetic glycopolymer–ligands toward lectins could be tuned using controlled radical polymerization techniques..
53. Nagao Masanori, Hoshino Yu, Miura Yoshiko, Quantitative preparation of multiblock glycopolymers bearing glycounits at the terminal segments by aqueous reversible addition–fragmentation chain transfer polymerization of acrylamide monomer, Journal of Polymer Science, Part A: Polymer Chemistry, 10.1002/pola.29344, 57, 857-861, 2019,57,857-861, 2019.03.
54. Terada, Y.; Hoshino, Y.; Miura, Y., “Glycopolymers mimicking GM1 gangliosides: Cooperativity of galactose and neuraminic acid for cholera toxin recognition, Chemistry–An Asian Journal, 10.1002/asia.201900053, 14, 1021-1027, Chemistry–An Asian Journal 2019,14,1021-1027. (DOI: doi.org/10.1002/asia.201900053), 2019.03.
55. Yu Hoshino, Kazushi Imamura, Tomohiro Gyobu, Ikuo Taniguchi, Akira Hamasaki, Chie Yamashita, Takeshi Watanabe, Yoshiko Miura, , Monolayer, composite, gas separation material, filter, gas separation device and method for manufacturing composite, United States Patent Application, 2019.03, A monolayer membrane containing gelling polymer particles having at least one of a basic functional group and an acidic functional group, and having a thickness of less than 5 μm. A composite having a porous carrier and gelling polymer particles having at least any one of a basic functional group and an acidic functional group and filling up the surface pores of the porous carrier. The invention can provide a novel material capable of efficiently separating an acid gas from a mixed gas..
56. Hiroyuki Koidea, KeiichiYoshimatsu,Yu Hoshino, Saki Ariizumi, Anna Okishima, Takafumi Ide, Hiromichi Egami, Yoshitaka Hamashima, Yuri Nishimura, Hiroaki Kanazawa, Yoshiko Miura, Tomohiro Asai, Naoto Oku, Kenneth J.Shea , Sequestering and inhibiting a vascular endothelial growth factor in vivo by systemic administration of a synthetic polymer nanoparticle, Journal of Controlled Release, 295, 13-20., https://doi.org/10.1016/j.jconrel.2018.12.033, Journal of Controlled Release, 295, 13-20., 2019.02.
57. Tomohiro Fukuda, Sotaro Tsuji, Yoshiko Miura, Glycopolymer preparation via post-polymerization modification using N-succinimidyl monomers, Polymer Journal, 10.1038/s41428-019-0170-y, 51, 617-625, Polym J 51, 617–625 (2019)., 2019.02.
58. Yu Hoshino, Toshiki Jibiki, Masahiko Nakamoto, Yoshiko Miura, Reversible pKa Modulation of Carboxylic Acids in Temperature-Responsive Nanoparticles through Imprinted Electrostatic Interactions, ACS applied materials & interfaces, DOI: 10.1021/acsami.8b11397, ACS applied materials & interfaces, 10(37), 31096-31105., 2018.08.
59. Takahiro Oh, Masanori Nagao, Yu Hoshino , and Yoshiko Miura, Self-Assembly of a Double Hydrophilic Block Glycopolymer and the Investigation of Its Mechanism, Langmuir, 10.1021/acs.langmuir.8b01527, 2018.07.
60. Hikaru Matsumoto, Takanori Akiyoshi, Yu Hoshino, and Yoshiko Miura, Size-tuned hydrogel network of palladium-confining polymer particles: a highly active and durable catalyst for Suzuki coupling reactions in water and ambient temperature, Polymer Jornal, 10.1038/ s41428-018-0102-2, 2018.07.
61. #Seiji KAMBA, Hirokazu SETO, Takashi KONDO, Yoshiko MIURA, Verification of the Universal Versatility of a Quantitative Protein Measurement Technique Using a Metal Mesh Device, Analytical Science, 10.2116/analsci.17P523, 34, 7, 765-770, 2018,34(7), 765-770, 2018.07, When proteins are attached to microstructures such as a metal mesh device, changes in their optical properties occur. These changes have been characterized based on actual measurements in the infrared region of the spectrum. We have previously theoretically and experimentally demonstrated the optical changes associated with streptavidin. Here, we investigate three types of proteins: avidin, BSA, and lysozyme. The three proteins were adsorbed onto three types of metal mesh devices having different resonant frequencies, and the corresponding spectra were measured in the infrared region. The change in the frequency of the dip point in the spectrum was extracted to quantitatively determine the quantity of protein; these results were correlated with the quantitative measurements obtained by electrophoresis. By examining three types of different proteins, it was verified that a variety of proteins can be measured based on the optical characteristics of metal mesh devices..
62. Masanori Nagao, Jayeeta Sengupta, Diana Diaz-Dussan, Madeleine Adam, Meng Wu, Jason Acker, Robert Ben, Kazuhiko Ishihara, Hongbo Zeng, Yoshiko Miura, Ravin Narain , Synthesis of Highly Biocompatible and Temperature-Responsive Physical Gels for Cryopreservation and 3D Cell Culture, ACS Applied Bio Materials, DOI: 10.1021/acsabm.8b00096, ACS Applied Bio Materials, 2018, 1.2: 356-366., 2018.07.
63. Xinnan Cui, Tatsuya Murakami, Yukihiko Tamura, Kazuhiro Aoki, Yu Hoshino, and Yoshiko Miura, Bacterial Inhibition and Osteoblast Adhesion on Ti Alloy Surfaces Modified by Poly(PEGMA-r-Phosmer) Coating, ACS Appl. Mater. Interfaces, 10.1021/acsami.8b07757, 10, 28, 23674-23681, 2018, 10 (28), 23674–23681, 2018.06, We have synthesized and immobilized PEGMA500-Phosmer to Ti6Al4V surfaces by a simple procedure to reduce bacteria-associated infection without degrading the cell response. Adhered bacteria coverage was lessened to 1% on polymer-coated surfaces when exposed to Escherichia coli, Staphylococcus epidermidis, and Streptococcus mutans. Moreover, PEGMA500-Phosmer and homoPhosmer coatings presented better responses to MC3T3-E1 preosteoblast cells when compared with the results for PEGMA2000-Phosmer-coated and raw Ti alloy surfaces. The behavior of balancing bacterial inhibition and cell attraction of the PEGMA500-Phosmer coating was explained by the grafted phosphate groups, with an appropriate PEG brush length facilitating greater levels of calcium deposition and further fibronectin adsorption when compared with that of the raw Ti alloy surface..
64. Seiji KAMBA, Hirokazu SETO, Takashi KONDO, Yoshiko MIURA, Regulating Detectable Optical Domain in Sensing Technology Using Metal Mesh Devices and Detection of Submicron-size Particle, Analytical Sciences, doi.org/10.2116/analsci.17P506, 34, 5, 547-552, 2018, 34(5), 547-552, 2018.05, A metal mesh device has a structure in which through-holes of the same shape are periodically placed on a thin metal film, and the selection of such a structure makes it possible to sense objects of various sizes. In this study, we showed the structure of the metal mesh device and the relationship between the detectable optical domain and the size of the objects to be measured. In addition, from measurement of changes in electromagnetic wave transmission characteristics of the metal mesh device due to specific adsorption of particles with a mean diameter of 100 nm with surface modification with Streptavidin to a metal mesh device fixed with biotin, we showed that even large particles can be sensed. Based on these examinations, we showed that, by using a metal mesh device with detectable optical domain corresponding to the size of objects, even objects that are larger than protein can be sensed..
65. Hikaru Matsumoto, Hirokazu Seto, Takanori Akiyoshi, Makoto Shibuya, Yu Hoshino , Yoshiko Miura, Macroporous Gel with a Permeable Reaction Platform for Catalytic Flow Synthesis, ACS Omega, DOI: 10.1021/acsomega.7b00909, 2, 12, 8796-8802, 2017, 2 (12), pp 8796–8802, 2017.12, [URL].
66. Xinnan Cui, Tatsuya Murakami, Yu Hoshino, Yoshiko Miura, Anti-biofouling phosphorylated HEMA and PEGMA block copolymers show high affinity to hydroxyapatite, Colloids and Surfaces B: Biointerfaces, 10.1016/j.colsurfb.2017.09.038, 160, 289-296, 2017.12, [URL], Four types of phosphorylated 2-hydroxyethyl methacrylate and poly(ethylene glycol) methyl ether methacrylate (PEGMA) block copolymers were synthesized by reversible addition fragmentation chain transfer (RAFT) polymerization and post-phosphorylation. These polymers were composed of different phosphate segments and similar PEG brushes. Polymers with defined phosphate segments were investigated to determine the optimal bonding affinity to hydroxyapatite (HAp). Polymers containing short phosphate segments (as low as 23 mer) were capable of immobilizing on HAp surfaces in situ in a short coating time with considerable durability. After surface modification, the dense PEG brushes altered the interfacial properties of HAp. The protein adsorption on the polymer-grafted HAp was drastically reduced compared with the bare HAp. Furthermore, the presence of the PEG brushes on the HAp surface resulted in bacterial inhibition. The polymer with the shortest phosphate segment (23 mer) showed superior inhibition ability..
67. K. Jono ,M. Nagao , T. Oh , S. Sonoda , Y. Hoshino, Y. Miura, Controlling the lectin recognition of glycopolymers via distance arrangement of sugar blocks, Chem. Commun, DOI: 10.1039/C7CC07107H (Communication), 54, 82-85, 2018, 54, 82-85, 2017.11, [URL], The arrangement of sugars in glycopolymers contributes to their recognition. The molecular recognition of proteins was controlled by the living radical polymerization of glycopolymers. The glycopolymers were prepared by the copolymerization of propargyl methacrylate (Pr-MA) and triethyleneglycol methacrylate (TEG-MA) via living radical polymerization with a reversible addition–fragmentation glycopolymer chain transfer (RAFT) reagent and by subsequent sugar conjugation by click chemistry. The block copolymers were prepared by the polymerization of Pr-MA and TEG-MA. The molecular recognition of glycopolymers was analyzed using the fluorescence quenching of lectin and found to be dependent on the glycopolymer structures. Two-site binding of glycopolymers to concanavalin A (ConA) was attained by both the glycopolymer with a 105-mer and the tri-block glycopolymer with a 103-mer. Glycopolymers with either a 27- or 54-mer showed much weaker interaction because of one-site binding. The molecular recognition of the glycopolymer was controlled by the arrangement and size of the sugar cluster and not by the sugar density..
68. Masanori Nagao, Yurina Fujiwara, Teruhiko Matsubara,Yu Hoshino,Toshinori Sato, oshiko Miura, Design of Glycopolymers Carrying Sialyl Oligosaccharides for Controlling the Interaction with the Influenza Virus, Biomacromolecules, DOI: 10.1021/acs.biomac.7b01426, 18, 12, 4385-4392, 2017, 18 (12), pp 4385–4392, 2017.11, [URL], We designed glycopolymers carrying sialyl oligosaccharides by “post-click” chemistry and evaluated the interaction with the influenza virus. The glycopolymer structures were synthesized in a well-controlled manner by reversible addition–fragmentation chain transfer polymerization and the Huisgen reaction. Acrylamide-type monomers were copolymerized to give hydrophilicity to the polymer backbones, and the hydrophilicity enabled the successful introduction of the oligosaccharides into the polymer backbones. The glycopolymers with different sugar densities and polymer lengths were designed for the interaction with hemagglutinin on the virus surface. The synthesized glycopolymers showed the specific molecular recognition against different types of influenza viruses depending on the sugar units (6′- or 3′-sialyllactose). The sugar density and the polymer length of the glycopolymers affected the interaction with the influenza virus. Inhibitory activity of the glycopolymer against virus infection was demonstrated..
69. Yu Hoshino,Takaaki Miyoshi , Masahiko Nakamoto,Yoshiko Miura, Wide-range p K a tuning of proton imprinted nanoparticles for reversible protonation of target molecules via thermal stimuli, J. Mater. Chem. B,, 10.1039/C7TB02107K, 5, 9204-9210, 2017, 5, 9204-9210, 2017.11, [URL], pKa tuning of Brønsted acids in synthetic nano-materials is of great importance for the design of ion exchange and bio-/molecular-separation media and polymer catalysis. It has been reported that hydrogel nanoparticles with carboxylic acids that show large and reversible pKa shifts in response to thermal stimuli can be prepared by copolymerization of N-isopropylacrylamide (NIPAm), acrylic acids (AAc) and N,N′-methylene bisacrylamide (BIS) via the proton imprinting polymerization process. However, the reported range of pKa shifts is limited to the range of 5.3 to 7.5. In this study, we report a procedure to prepare proton imprinted NPs that show pKa shifts in the tuned pKa range and demonstrate applications of the NPs. pKa values ranging from 4.3 to 8.7 were achieved by designing the structure of monomers containing carboxylic acids and applying the proton imprinting procedure. It was demonstrated that proton-imprinted NPs with different pKa values could be used for the reversible and selective protonation of target molecules which have specific pKa values. Our results establish the generality of the proton imprinting procedure and provide a guide for designing stable and inexpensive materials for sophisticated purification processes..
70. HirohikoIse,Sadanori Yamasaki,Kazuaki Sueyoshi,Yoshiko Miura, Elucidation of GlcNAc-binding properties of type III intermediate filament proteins, using GlcNAc bearing polymers, Genes to Cells, DOI: 10.1111/gtc.12535, 22, 10, 900-917, Volume 22, Issue 10, October 2017, Pages 900–917 ", 2017.10, [URL], Vimentin, desmin, glial fibrillary acidic protein (GFAP) and peripherin belong to type III intermediate filament family and are expressed in mesenchymal cells, skeletal muscle cells, astrocytes and peripheral neurons, respectively. Vimentin and desmin possess N‐acetyl‐d‐glucosamine (GlcNAc)‐binding properties on cell surfaces. The rod II domain of these proteins is a GlcNAc‐binding site, which also exists in GFAP and peripherin. However, the GlcNAc‐binding activities and behaviors of these proteins remain unclear. Here, we characterized the interaction and binding behaviors of these proteins, using various well‐defined GlcNAc‐bearing polymers synthesized by radical polymerization with a reversible addition‐fragmentation chain transfer reagent. The small GlcNAc‐bearing polymers strongly interacted with HeLa cells through vimentin expressed on the cell surface and interacted with vimentin‐, desmin‐, GFAP‐ and peripherin‐transfected vimentin‐deficient HeLa cells. These proteins present high affinity to GlcNAc‐bearing polymers, as shown by surface plasmon resonance. These results show that type III intermediate filament proteins possess GlcNAc‐binding activities on cell surfaces. These findings provide important insights into novel cellular functions and physiological significance of type III intermediate filaments..
71. Seiji Kamba, Hirokazu Seto, Takashi Kondo, Yoshiko Miura, Quantitative Measurement of Protein using Metal Mesh Device, Analytical Science, 10.2116/analsci.33.1033, 33, 9, 1033-1039, 33 巻 (2017) 9 号 p. 1033-1039, 2017.09, [URL], 抄録
Biosensing of protein adsorption with metal mesh device (MMD) was investigated by computational calculations and experiments. Electromagnetic field computation was carried out with a single unit cell of MMD. Equivalent circuit model of MMD on the single unit cell was assumed, and the biosensing with MMD was analyzed in detail by computational calculation and experimental measurements. The dip frequency of MMD was shifted by adsorption of protein on MMD. The shift of dip frequency of MMD was proportional to the amount of protein adsorption. The sensitivity of MMD biosensing was dependent on the microstructure of MMD, and proportional to the square of the dip frequency. The refinement of MMD structure can improve the sensitivity of protein detection.
72. Yusuke Yonamine, Yuta Suzuki,Takuro Ito,Yoshiko Miura,Keisuke Goda,Yasuyuki Ozeki,Yu Hoshino, Monitoring photosynthetic activity in microalgal cells by raman spectroscopy with deuterium oxide as a tracking probe, ChemBioChem, 10.1002/cbic.201700314, 18, 20, 2063-2068, Volume 18, Issue 20,October 18, 2017, Pages 2063–2068 ", 2017.09, [URL], Microalgae offer great potential for the production of biofuel, but high photosynthetic activity is demanded for the practical realisation of microalgal biofuels. To this end, it is essential to evaluate the photosynthetic activity of single microalgal cells in a heterogeneous population. In this study, we present a method to monitor the photosynthetic activity of microalgae (in particular Euglena gracilis, a microalgal species of unicellular, photosynthetic, flagellate protists as our model organism) at single‐cell resolution by Raman spectroscopy with deuterium from deuterium oxide (D2O) as a tracking probe. Specifically, we replaced H2O in culture media with D2O up to a concentration of 20 % without disturbing the growth rate of E. gracilis cells and evaluated C−D bond formation as a consequence of photosynthetic reactions by Raman spectroscopy. We used the probe to monitor the kinetics of the C−D bond formation in E. gracilis cells by incubating them in D2O media under light irradiation. Furthermore, we demonstrated Raman microscopy imaging of each single E. gracilis cell to discriminate deuterated cells from normal cells. Our results hold great promise for Raman‐based screening of E. gracilis and potentially other microalgae with high photosynthetic activity by using D2O as a tracking probe..
73. Hirokazu Seto, Makoto Shibuya, Hikaru Matsumoto, Yu Hoshino, Yoshiko Miura, Glycopolymer monoliths for affinity bioseparation of proteins in a continuous-flow system: glycomonoliths, J. Mater. Chem., 10.1039/C6TB02930B, 5, 1148-1154, 2017.05, In this study, macroporous materials, called glycomonoliths, were produced from saccharide-containing monomers, and used for affinity bioseparation of proteins in a continuous-flow system. The porous structure formation of the glycomonoliths involved polymerization-induced phase separation of the polyacrylamide unit. The pore size could be controlled between several hundred nanometers and several micrometers by changing the alcohol used as the porogenic solvent during the preparation of the monolith. The glycomonolith pores allowed for the permeation of solutions through the monoliths, which meant that they could be used in a continuous-flow system. The adsorption capacities of the glycomonoliths for the saccharide-binding protein (concanavalin A) were larger than that of a glycopolymer-grafted material because of the higher saccharide densities in the monoliths than the grafted material. When concanavalin A was eluted from the glycomonolith, the concentration of concanavalin A in the effluent was up to 11 times higher than that in the feed solution. The adsorption of concanavalin A to the glycomonolith was specific, even in the presence of other proteins..
74. 福田知博, 三浦佳子, デンドリティック糖質界面が示す生体機能, 高分子論文集, doi.org/10.1295/koron.2016-0046, 74, 1, 1-9, 2017.05.
75. Hikaru Matsumoto, Hirokazu Seto, Takanori Akiyoshi, Makoto Shibuya, Yu Hoshino, Yoshiko Miura, Macroporous Monolith with Polymer Gel Matrix as Continuous-Flow Catalytic Reactor, Chemistry Letters, 10.1246/cl.170360, 46, 8, 1065-1067, 2017, Vol.46, No.8, 1065-1067, 2017.05, [URL], A macroporous monolith comprising a polymer gel matrix was developed for application in continuous-flow catalytic reactions. Nanosized Pd(0) particles were loaded in a poly(N-isopropylacrylamide)-gel-based monolith by Pd(II) adsorption and subsequent reduction. The permeability of the Pd(0)-loaded monolith was compared with a commercial membrane filter with a pore size of several micrometers. The Pd(0)-loaded monolith exhibited excellent productivity in a continuous-flow Suzuki coupling reaction. Moreover, the Pd(0)-loaded monolith showed sustained performance over a 7-day period without Pd leaching..
76. Mengchen Yue, Kenta Imai, Yoshiko Miura, Yu Hoshino, Design and preparation of thermo-responsive vinylamine-containing micro-gel particles for reversible absorption of carbon dioxide, Polymer Journal, doi:10.1038/pj.2017.28, 49, 601-606, volume 49, pages 601–606 (2017), 2017.05, [URL], To obtain a temperature-responsive CO2 absorbent with a high amine content, temperature-responsive gel particles (GPs) consisting of poly(N-isopropylacrylamide-co-polyvinylamine) (poly(NIPAm-co-VAm)) were designed and prepared. Stable poly(N-isopropylacrylamide) GPs with a high N-vinylformamide (NVF) content were prepared in aqueous media by optimization of the concentrations of the surfactant and monomers used in the polymerization step. GPs with a high polyvinylamine (pVAm) content up to 3.2 mmol amine per g GPs (~30 mol%) were prepared as a stable aqueous solution via the complete and selective hydrolysis of pNVF in the poly(NIPAm-co-NVF) GPs in a methanol solution, then dialyzed against water. The GPs with 3.2 mmol amine per g GPs pVAm showed a volume phase transition at a temperature of ~65 °C. Conductivity experiments established that the aqueous solution of the poly(NIPAm-co-VAm) GPs reversibly absorbed CO2 in response to a small thermal stimulus (30–75 °C). In addition, the foaming of amine-functionalized GP solutions during CO2 bubbling was prevented by increasing the amount of crosslinking in the GPs..
77. Hiroyuki Koide, Keiichi Yoshimatsu, Yu Hoshino, Shih-Hui Lee, Saki Arizumi, Yudai Narita, Yusuke Yonamine, Adam C. Weisman, Yuri Nishimura, Naogo Oku, Yoshiko Miura, Kenneth J Shea, A polymer nanoparticle with engineered affinity for a vascular endothelial growth factor (VEGF165), Nature Chemistry, 10.1038/nchem.2749, 9, 715-722, 9, pages 715–722 (2017), 2017.03, [URL], Protein affinity reagents are widely used in basic research, diagnostics and separations and for clinical applications, the most common of which are antibodies. However, they often suffer from high cost, and difficulties in their development, production and storage. Here we show that a synthetic polymer nanoparticle (NP) can be engineered to have many of the functions of a protein affinity reagent. Polymer NPs with nM affinity to a key vascular endothelial growth factor (VEGF165) inhibit binding of the signalling protein to its receptor VEGFR-2, preventing receptor phosphorylation and downstream VEGF165-dependent endothelial cell migration and invasion into the extracellular matrix. In addition, the NPs inhibit VEGF-mediated new blood vessel formation in Matrigel plugs in vivo. Importantly, the non-toxic NPs were not found to exhibit off-target activity. These results support the assertion that synthetic polymers offer a new paradigm in the search for abiotic protein affinity reagents by providing many of the functions of their protein counterparts..
78. Mengchen Yue, Kenta Imai, Chie Yamashita, Yoshiko Miura, Yu Hoshino, Effects of Hydrophobic Modifications and Phase Transitions of Polyvinylamine Hydrogel Films on Reversible CO2 Capture Behavior: Comparison between Copolymer Films and Blend Films for Temperature-Responsive CO2 Absorption, Macromolecular Chemistry and Physics, 10.1002/macp.201600570, 218, 2017.02.
79. Hikaru Matsumoto, Hirokazu Seto, Yu Hoshino, Yoshiko Miura, Poly(N-isopropylacrylamide) gel-based macroporous monolith for continuous-flow recovery of palladium(II) ions, Journal of Applied Polymer Science, 10.1002/app.44385, 134, 4, 44385, 2017.01.
80. Yuhei Terada, Shuhei Shinohara, Tatsuya Murakami, Kaoru Tamada, Yu Hoshino, Yoshiko Miura, SPR study for analysis of water-soluble glycopolymer interface and molecular recognition properties, Polymer Journal, 10.1038/pj.2016.99, 49, 255-262, 2016.08.
81. Adam Michael Maley, Yuhei Terada, Shunsuke Onogi, Kenneth J. Shea, Yoshiko Miura, Robert M. Corn, Measuring Protein Binding to Individual Hydrogel Nanoparticles with Single Nanoparticle SPRI Microscopy, J. Phys. Chem. C, 10.1021/acs.jpcc.6b05700, 2016.07, The specific binding and uptake of protein molecules to individual hydrogel nanoparticles is measured with real-time single nanoparticle surface plasmon resonance imaging (SPRI) microscopy. Nanoparticles that adsorb onto chemically modified gold thin films interact with traveling surface plasmon polaritons and create individual point diffraction patterns in the SPRI microscopy differential reflectivity images. The intensity of each point diffraction pattern depends on the integrated refractive index of the nanoparticle; an increase in this single nanoparticle point diffraction intensity (∆%RNP) is observed for nanoparticles that bind proteins. SPRI adsorption measurements can be used to measure an average increase in ∆%RNP that can be correlated with bulk dynamic light scattering measurements. Moreover, the distribution of ∆%RNP values observed for individual nanoparticles can be used to learn more about the nature of the protein-nanoparticle interaction. As a first example, the binding of the lectin Concanavalin A to 180 nm N-isopropylacrylamide hydrogel nanoparticles that incorporate a small percentage of mannose sugar monomer units is characterized..
82. Hasegawa, M, Yamamoto, K, Shirai-Kitanishi, E, Mori, K, Inoue, Y, Inagaki, Y, Sasaki, R, Mizukami, T, Shirai, M, Yoshiko Miura, Ogawa, Y, Banju, M, Kamba, S, Kondo, T, Surface coating of a metal mesh device sensor with gold to improve the separation and sensing of mammalian cell, IEEE Sensors Journal, 16, 13, 5129-5135, IEEE Sensors Journal, 2016, 16(13): 5129-35., 2016.07.
83. Masanori Nagao, Yuuki Kurebayashi, Hirokazu Seto, Tadanobu Takahashi, Takashi Suzuki, Yu Hoshino, Yoshiko Miura, Polyacrylamide backbones for polyvalent bioconjugates using “post-click” chemistry”, Polymer Chemistry, 2016.07.
84. Hirokazu Seto, Kenta Imai, Yu Hoshino, Yoshiko Miura, Polymer microgel particles as basic catalysts for Knoevenagel condensation in water, Polymer Journal, 10.1038/pj.2016.44, 2016.05.
85. Yoshiko Miura, Yu Hoshino, Hirokazu Seto, Glycopolymer Nanobiotechnology, Chemical Reviews, 10.1021/acs.chemrev.5b00247, 116, 1673-1692, 2016.02, Previous studies have clearly shown the importance of the multivalent effect in saccharide–protein interactions. To investigate the multivalent effect, the use of multivalent compounds or “glycoclusters” is indispensable, and many groups have reported syntheses of glycocluster compounds. Examples of glycoclusters include liposomes with glycolipids, glycocalixarenes, glycocyclodextrins, glycopeptides, and glycopolymers. Among the various synthetic glycoclusters, glycopolymers have been the subject of much attention . In this review, we define glycopolymers as polymers carrying pendant saccharides. Since glycopolymers have larger valencies than other multivalent compounds, they show the largest amplification effects in molecular recognition. Glycopolymers are able to be prepared as nanomaterials by controlled polymerization. In this section of the review, we discuss glycopolymers and their application for biotechnology..
86. Xinnan Cui, Hirokazu Seto, Tatsuya Murakami, Yu Hoshino, Yoshiko Miura, Inhibition of Bacterial Adhesion on Hydroxyapatite Model Teeth by Surface Modification with PEGMA-Phosmer Copolymers, ACS Biomater. Sci. Eng, 10.1021/acsbiomaterials.5b00349, 2, 2, 205-212, 2016.02, Modification of the interface properties on hydroxyapatite and tooth enamel surfaces was investigated to fabricate bacterial resistance in situ. A series of copolymers containing pendants of poly(ethylene glycol) methyl ether methacrylate (PEGMA) and ethylene glycol methacrylate phosphate (Phosmer) were polymerized by conventional free radical polymerization and changing the feed ratio of monomers. The copolymers were immobilized on hydroxyapatite and tooth enamel via the affinity of phosphate groups to hydroxyapatite to form the stable and durable polymer brushes on the surfaces. The amounts of polymer immobilized depended on the phosphate group ratio in the copolymers. Surface modification altered the interfacial properties of hydroxyapatite and inhibited bacterial adhesion. Copolymers containing 40–60% PEGMA segments showed a significant inhibitory effect on bacterial adhesion of S. epidermidis both in the presence and absence of plaque model biomacromolecules..
87. Masanori Nagao, Yuuki Kurebayashi, Hirokazu Seto, Tomonari Tanaka, Tadanobu Takahashi, Takashi Suzuki, Yu Hoshino, Yoshiko Miura, Synthesis of well-controlled glycopolymers bearing oligosaccharides and their interactions with influenza viruses, Polymer Journal, 48, 745-749, 2016, 48, 745–749, 2016.02.
88. Masahiko Nakamoto, Tadashi Nonaka, Kenneth J. Shea, Yoshiko Miura, Yu Hoshino, Design of Synthetic Polymer Nanoparticles that Facilitate Resolubilization and Refolding of Aggregated Positively Charged Lysozyme, J. Am. Chem. Soc.,, 10.1021/jacs.5b12600, 138, 13, 4282-4285, 2016,138,4282-4285, 2016.02.
89. Masahiko Nakamoto, Tadashi Nonaka, Kenneth J Shea, Yoshiko Miura, Yu Hoshino, Design of Synthetic Polymer Nanoparticles That Facilitate Resolubilization and Refolding of Aggregated Positively Charged Lysozyme, Journal of the american chemical society, 10.1021/jacs.5b12600, 138, 13, 4282-4285, 2016.02.
90. Yoshiko Miura, Tomohiro Fukuda, Hirokazu Seto, Yu Hoshino, Development of Glycosaminoglycan Mimetics with Glycopolymers, Polymer Journal, 10.1038/pj.2015.110, in press, 2015.11, Glycosaminoglycans (GAGs) are polysaccharides found in living systems that have key biological roles and function as polyelectrolytes owing to their large number of sulfate groups. There have been many reports describing the syntheses of GAGs and the development of GAG mimetics and analogs. The preparation of such GAG mimics has utilized versatile methods ranging from total syntheses to synthetic polymer chemistry approaches. The core of GAG mimetic production is the fusion of complex chemical structures with polymeric properties. Multivalent interactions of the saccharides with specific biological targets, such as proteins, are an essential function of GAGs and other multivalent saccharides. In this review, methods for generating GAGs from glycopolymers are presented and research reports describing the functional characterization of the synthesized GAGs are outlined..
91. Tomohiro Fukuda, Erino Matsumoto, Yoshiko Miura, Interaction between Multimeric Sulfated Saccharides and Alzheimer Amyloid beta (1-42), Chemistry Letters, 10.1246/cl.150633, 44, 11, 1482-1484, 2015.11, The pathogenesis of Alzheimer’s disease is known to be related to the glycosaminoglycans that are associated with the deposition of amyloid beta (Aβ) peptides. We prepared heparin-mimicking multimeric saccharides and investigated their interactions with Aβ peptides in solution. The results showed that multimeric saccharides, especially the dimeric saccharide, strongly inhibited β-sheeted Aβ aggregation as assessed by the thioflavin-T (Th-T) assay, average zeta potential measurements and atomic force microscopy (AFM). This result suggested that the amyloidosis of Aβ (1-42) was affected by the multivalency of saccharides even in the solution..
92. Yoshiko Miura, Tomohiro Fukuda, Hirokazu Seto, Yu Hoshino, Development of glycosaminoglycan mimetics using glycopolymers, Polymer Journal, 10.1038/pj.2015.110, 48, 229-237, 2016,48,229-237, 2015.11.
93. LEE, H., Hoshino, Y., Wada, Y., Arata, Y., Maruyama, A., Miura Y., Minimization of Synthetic Polymer Ligands for Specific Recognition and Neutralization of a Toxic Peptide., Journal of the American Chemical Society, 137, 34, 10878-10881, 2015, 137 (34), 10878-10881, 2015.08.
94. Yue, Mencheng, Yu Hoshino, Yoshiko Miura, Design rationale of thermally responsive microgel particle films that reversibly absorb large amounts of CO2: fine tuning the pKa of ammounium ions in the particles., Chemical Science, 10.1039/C5SC01978H, 6, 11, 6112-6123, 2015, 6 (11), 6112-6123, 2015.07, Herein we revealed the design rationale of thermally responsive gel particle (GP) films that reversibly capture and release large amounts of CO2 over a narrow temperature range (30–75 °C). The pKa value of ammonium ions in the GPs at both the CO2 capture temperature (30 °C) and release temperature (75 °C) is found to be the primary factor responsible for the stoichiometry of reversible CO2 capture by the amines in the GP films. The pKa values can be tuned by the properties of GPs such as volume phase transition temperature (VPTT), size, swelling ratio, and the imprinted microenvironment surrounding the amines. The optimal GP obtained according to the design rationale showed high capture capacity (68 mL CO2 per g dry GPs, 3.0 mmol CO2 per g dry GPs), although the regeneration temperature was as low as 75 °C. We anticipate that GP films that reversibly capture other acidic and basic gases in large amounts can also be achieved by the pKa tuning procedures..
95. Hirokazu Seto, Seiji Kamba, Takashi Kondo, Yuichi Ogawa, Yu Hoshino, Yoshiko Miura, Label-free Detection of Antigen Protein Using a Metal Mesh Device Surface-modified by an Antibody, ANALYTICAL SCIENCES, 31, 3, 173-176, 2015.03.
96. Hirokazu Seto, Tamami Yoneda, Takato Morii, Yu Hoshino, Yoshiko Miura, Membrane Reactor Immobilized with Palladium-Loaded Polymer Nanogel for Continuous-Flow Suzuki Coupling Reaction, AIChe Journal, 10.1002/aic.14653, 61, 2, 582-589, 2015. Vol 61 No.2 582-589, 2015.02.
97. Yu Hoshino, Yuka Arata, Haejoo Lee, Yusuke Yonamine, Shih-Hui Lee, Aki Yamasaki, Ryosuke Tsuhara, Katsuhiko Yano, Kenneth J Shea, Yoshiko Miura, Preparation of nanogel-immobilized porous gel beads for affinity separation of proteins: fusion of nano and micro gel materials, POLYMER JOURNAL, 10.1038/pj.2014.101, 47, 2, 220-225, 2015.02.
98. Yusuke Wada, Haejoo Lee, Yu Hoshino, Shunsuke Kotani, Kenneth J Shea, Yoshiko Miura, Design of multi-functional linear polymers that capture and neutralize a toxic peptide: a comparison with cross-linked nanoparticles, JOURNAL OF MATERIALS CHEMISTRY B, 10.1039/c4tb01967a, 3, 8, 1706-1711, 2015.01.
99. Wong, Yoke-Ming, Yu Hoshino, Sudesh, Kumar, Yoshiko Miura, Numata, Keiji, Optimization of Poly(N-isopropylacrylamide) as an Artificial Amidase, BIOMACROMOLECULES, 10.1021/bm501671, 16, 1, 595-604, 2015.01.
100. Yusuke Wada, Haejoo Lee, Shunsuke Kotani, Yu Hoshino, Kenneth J. Shea, Yoshiko Miura, Design of multi-functional linear polymers that capture and neutralize a toxic peptide: a comparison with cross-linked nanoparticles, J. Mater. Chem. B, 10.1039/C4TB01967A, 3, 1706-1711, J. Mater. Chem. B, 2015, 3, 1706-1711, 2015.01, In this paper, a library of multi-functional linear poly-N-isopropylacrylamide (pNIPAm) polymers having a range of molecular weights and functional groups were synthesized and their interaction with the hemolytic peptide, melittin, was examined. The linear pNIPAm (LPs) containing both tert-butyl group and carboxylic acids bound with the peptide by a combination of hydrophobic and electrostatic interactions and neutralized its toxicity. The melittin binding capacity and affinity of each LP was quantified and further compared with cross-linked multi-functional nanogel particles (NPs) having same combination of functional groups. The binding capacity of the LPs (weight of captured melittin/weight of LP) was independent of their molecular weight and was three times higher than that of previously reported NPs. The binding constant depended on the molecular weight of the LPs, showing the highest value of 1.1 × 108 (M−1) for a ∼1000 mer linear polymer with 40% tert-butyl group and 20% carboxylic acid. Comparison of the interactions of the LPs and NPs suggested the importance of the flexibility of the polymer chain in order to achieve high binding capacity and affinity..
101. Tomonari Tanaka, Hiedeki Ishitani, Yoshiko Miura, Kenta Oishi, Tadanobu Takahashi, Takashi Suzuki, Shin-ichiro Shoda, Yoshiharu Kimura, Protecting-Group-Free Synthesis of Glycopolymers Bearing Sialyloligosaccharide and Their High Binding with the Influenza Virus, ACS Macro Lett 3 (10), pp 1074–1078, 10.1021/mz500555x, 3, 10, 1074-1078, 2014.10.
102. Yu Hoshino, Haejoo Lee, Yoshiko Miura, Interaction between synthetic particles and biomacromolecules: fundamental study of nonspecific interaction and design of nanoparticles that recognize target molecules, POLYMER JOURNAL, 10.1038/pj.2014.33, 46, 9, 537-545, 2014.09.
103. Hirokazu Seto, Seiji Kamba, Takashi Kondo, Makoto Hasegawa, Shigeki Nashima, Yoshinobu Ebara, Yuichi Ogawa, Yu Hoshino, Yoshiko Miura, Metal Mesh Device Sensor Immobilized with a Trimethoxysilane-Containing Glycopolymer for Label-Free Detection of Proteins and Bacteria, ACS Appl. Mater. Interfaces, 2014, 6 (15), pp 13234–1324, 10.1021/am503003v, 6, 15, 13234-13241, 2014.07.
104. Yu Hoshino, Ryohei C. Ohashi, Yoshiko Miura, Rational Design of Synthetic Nanoparticles with a Large Reversible Shift of Acid Dissociation Constants: Proton Imprinting in Stimuli Responsive Nanogel Particles, Advanced Materials, 10.1002/adma.201305957, 26, 22, 3718-3723, 2014.06.
105. Masahiko Nakamoto, Yu Hoshino, Yoshiko Miura, Effect of Physical Properties of Nanogel Particles on the Kinetic Constants of Multipoint Protein Recognition Process, Biomacromolecules, 10.1021/bm401536v, 15, 2, 541-547, 2014.02.
106. Yuhei Terada, Tatsuro Endo, Hirokazu Seto, Hideaki Hisamoto, Yoshiko Miura, Signal amplified two-dimensional photonic crystal biosensor immobilized with glyco-nanoparticles, Journal of Materials Chemistry B, 10.1039/C4TB00028E, 2, 3324-3332, 2014.02.
107. Mengchen Yue, Yu Hoshino, Yukinori Oshiro, Kazushi Imamura, Yoshiko Miura, Temperature-Responsive Microgel Films as Reversible Carbon Dioxide Absorbents in Wet Environment, Angewandte Chemie, 10.1002/ange.201309758, 126, 10, 2692-2695, 2014.01, Hydrogel films composed of temperature-responsive microgel particles (GPs) containing amine groups work as stimuli-responsive carbon dioxide absorbent with a high capacity of approximately 1.7 mmol g−1. Although the dried films did not show significant absorption, the reversible absorption capacity dramatically increased by adding a small amount of water (1 mL g−1). The absorption capacity was independent of the amount of added water beyond 1 mL g−1, demonstrating that the GP films can readily be used under wet conditions. The amount of CO2 absorbed by the GP films was proportional to their thickness up to 200–300 μm (maximum capacity of about 2 L m−2). Furthermore, the films consisting of GPs showed faster and greater absorption and desorption of CO2 than that of monolithic hydrogel films. These results indicated the importance of a fast stimulus response rate of the films that are composed of GPs in order to achieve long-range and fast diffusion of bicarbonate ions. Our study revealed the potential of stimuli-responsive GP films as energy-efficient absorbents to sequester CO2 from high-humidity exhaust gases..
108. Yuri Nishimura, Hiroki Shudo, Hirokazu Seto, Yu Hoshino, Yoshiko Miura, Syntheses of sulfated glycopolymers and analyses of their BACE-1 inhibitory activity, Bioorganic Medicinal Chemistry Letters, 10.1016/j.bmcl.2013.09.057, 23, 23, 6390-6395, Bioorganic & Medicinal Chemistry Letters
Volume 23, Issue 23, 1 December 2013, Pages 6390–6395, 2013.12.
109. Hirokazu Seto, Seiji Kamba, Takashi Kondo, Yuichi Ogawa, Yu Hoshino, Yoshiko Miura, Novel Detection Technique for Particulate Matter in Air Using Metal Mesh Device Sensors, Chemistry Letters, 10.1246/cl.131040, 43, 408-410, 2013.11, A novel technique for detection of particulate matter in air using metal mesh devices is proposed. Metal mesh device with square apertures was used as membrane filter and as band-pass filter. Frequency shifts in transmittance spectra of the metal mesh device collected with particulate matter had a linear relationship to the particulate matter concentrations with a high coefficient of determination. When metal mesh devices with different opening lengths were stacked, particulate matter was fractionalized by size..
110. Masami Takara, Masayuki Toyoshima, Hirokazu Seto, Yu Hoshino, Yoshiko Miura, Polymer-Modified Gold Nanoparticles via RAFT Polymerization: Detailed Study for a Biosensing Application, Polymer Chemistry, 10.1039/C3PY01001E, 5, 931-939, 2013.09.
111. Yutaro Ogata, Hirokazu Seto, Tatsuya Murakami, Yu Hoshino, Yoshiko Miura, Affinity Separation of Lectins Using Porous Membranes Immobilized with Glycopolymer Brushes Containing Mannose or N-Acetyl-D-Glucosamine, Membranes, 10.3390/membranes3030169, 3, 3, 169-181, 2013, 3(3), 169-181, 2013.08, Porous membranes with glycopolymer brushes were prepared as biomaterials for affinity separation. Glycopolymer brushes contained acrylic acid and D-mannose or N-acetyl-D-glucosamine, and were formed on substrates by surface-initiated atom transfer radical polymerization. The presence of glycopolymer brush was confirmed by X-ray photoelectron spectroscopy, contact angle, and ellipsometry measurements. The interaction between lectin and the glycopolymer immobilized on glass slides was confirmed using fluorescent-labeled proteins. Glycopolymer-immobilized surfaces exhibited specific adsorption of the corresponding lectin, compared with bovine serum albumin. Lectins were continuously rejected by the glycopolymer-immobilized membranes. When the protein solution was permeated through the glycopolymer-immobilized membrane, bovine serum albumin was not adsorbed on the membrane surface. In contrast, concanavalin A and wheat germ agglutinin were rejected by membranes incorporating D-mannose or N-acetyl-D-glucosamine, respectively. The amounts of adsorbed concanavalin A and wheat germ agglutinin was increased five- and two-fold that of adsorbed bovine serum albumin, respectively..
112. Hirokazu Seto, Chie Yamashita, Seiji Kamba, Takashi Kondo, Makoto Hasegawa, Matsuno, Mitsuhiro, Yuichi Ogawa, Yu Hoshino, Yoshiko Miura, Biotinylation of Silicon and Nickel Surfaces and Detection of Streptavidin as Biosensor, Langmuir, 10.1021/la401068n, 29, 30, 9457-9463, Langmuir, 2013, 29 (30), pp 9457–9463, 2013.07.
113. Hirokazu Seto, Takato Morii, Tamami Yoneda, Tatsuya Murakami, Hoshino Yu, Miura Yoshiko, Preparation of Palladium-loaded Polymer Nanoparticles with Catalytic Activity for Hydrogenation and Suzuki Coupling Reactions, Chemistry Letters, 42, 301-303, 2013.03.
114. Hoshino Yu, Kazushi Imamura, Mengchen Yue, Gen Inoue, Miura Yoshiko, Reversible absorption of CO2 triggered by phase transition of amine-containing micro- and nano-gel particles, J. Am. Chem. Soc, 134, 44, 18177–18180, 2012.10, Herein we report that an aqueous solution of temperature-responsive micro- and nanogel particles (GPs) consisting of N-isopropylacrylamide (NIPAm) and N-[3-(dimethylamino)propyl]methacrylamide (DMAPM) reversibly absorbs and desorbs CO2 via a phase transition induced by cooling and heating cycles (30–75 °C). Below the phase-transition temperature, most of the amines in the swollen GPs are capable of forming ion pairs with absorbed bicarbonate ions. However, above the phase-transition temperature, shrinkage of the GPs lowers the pKa and the number of amine groups exposed to water, thereby resulting in almost complete desorption of CO2. The GPs can reversibly absorb more than the DMAPM monomer and polymer without NIPAm, which indicates the importance of the temperature-responsive phase transition of polymers in determining the degree of absorption. The results show the potential of temperature-responsive polymer solutions as absorbents to sequester CO2 at a low energy cost..
115. Yoshiko Miura, Shunsuke Onogi, Tomohiro Fukuda, Syntheses and Biological Ability of Sulfo-Glycodendrimer via Click
Chemistry, Molecules, doi:10.3390/molecules171011877 , 17, 10, 11877-11896, 2012.10.
116. Yu Hoshino, Masahiko Nakamoto, and Yoshiko Miura, Control of Protein-Binding Kinetics on Synthetic Polymer Nanoparticles by Tuning Flexibility and Inducing Conformation Changes of Polymer Chains
, J. Am. Chem. Soc., DOI: 10.1021/ja306053s, 134, 37, 15209-15212, 2012.09.
117. Tomohiro FUkuda, Masaki Kawamura, Hikaru Mizuno, Miura Yoshiko, Glycosaminoglycan Model Polymers with Poly(γ-glutamate) Backbone to Inhibit Aggregation of β-Amyloid Peptide, Polymer journal, 45, 359-362, 2012.09.
118. 瀬戸 弘一, Chie Yamashita, Tatsuya Murakami, Takeshi Hasegawa, Miura Yoshiko, Surface Modification of Siliceous Materials Using Maleimidation and Various Functional Polymers Synthesized by Reversible Addition Fragmentation Chain Transfer Polymerization, ACS Applied Materials and Interfaces, DOI: 10.1021/am301637q, 4, 10, 5125-5133, 2012.09.
119. Yasuhiro Maeda, Akira Matsumoto, Yoshiko Miura and Yuji Miyahara, , "Preparation of alpha-Mannoside hydrogel and electrical detection of saccharide-protein interactions using the smart gel-modified gate field effect transistor",
, Nanoscale Res. Lett., 10.1186/1556-276X-7-108, 7, 108, 2012, 7, 108. , 2012.04.
120. Seto, Hirokazu; Ogata, Yutaro; Murakami, Tatsuya; Hoshino, Yu; Miura, Yoshiko , Selective Protein Separation Using Siliceous Materials with a Trimethoxysilane-Containing Glycopolymer, ACS Applied Materials & Interfaces, 10.1021/am2014713, 4, 1, 411-417, 2012, 4(1), 411-417, 2012.01, A copolymer with α-d-mannose (Man) and trimethoxysilane (TMS) units was synthesized for immobilization on siliceous matrices such as a sensor cell and membrane. Immobilization of the trimethoxysilane-containing copolymer on the matrices was readily performed by incubation at high heat. The recognition of lectin by poly(Man-r-TMS) was evaluated by measurement with a quartz crystal microbalance (QCM) and adsorption on an affinity membrane, QCM results showed that the mannose-binding protein, concanavalin A, was specifically bound on a poly(Man-r-TMS)-immobilized cell with a higher binding constant than bovine serum albumin. The amount of concanavalin A adsorbed during permeation through a poly(Man-r-TMS)-immobilized membrane was higher than that through an unmodified membrane. Moreover, the concanavalin A adsorbed onto the poly(Man-r-TMS)-immobilized membrane was recoverable by permeation of a mannose derivative at high concentration..
121. 三浦佳子、坂本祥吾、福田知博、由井伸彦, 硫酸化糖鎖高分子によるグリコサミノグリカンモデルポリマーの合成とアミロイド阻止機能, 高分子論文集, 69, 1, 47-53, 2012、69(1)、47-53, 2012.01, 6位硫酸化グルコサミンを結合させたポリロタキサン(PRX-6S-GlcNAc)を合成してアミロイドβ(1-40)に対する凝集抑制効果について検討した。10%の糖鎖含有量を持つPRX-6S-GlcNAcについては6位硫酸化グルコサミンの単体に比べて優れた凝集抑制能を示した。硫酸化糖修飾ポリロタキサンのアミロイド阻止機能については、糖鎖含有量やポリマーの添加量に依存があった。ポリロタキサンの糖鎖含有量が多くなると、アミロイド阻止機能は低下した。一方で、糖鎖修飾ポリロタキサンの量が増えるほど、アミロイド阻止機能は向上した。一方で、糖鎖修飾ポリロタキサンの量が増えるほどアミロイド阻止機能は向上した。ポリロタキサンの携帯はアミロイドβとの結合に必ずしも有利ではないが、一定のアミロイド阻止機能を発揮した。そして、PRX-6S-GlcNAcによる、アミロイド化抑制については原子間力顕微鏡による、形態観察によっても明らかになった。.
122. Matsumoto, Erino; Nishizawa, Kazuki; Fukuda, Tomohiro; Takai, Madoka; Miura, Yoshiko, Separation capability of proteins using microfluidic system with dendrimer modified surface , Transactions of the Materials Research Society of Japan, 36, 4, 541-544, 2011、36(4)、541-544, 2011.11.
123. Jin Ishii, Miyuki Chikae, Masayuki Toyoshima, Yoshiaki Ukita, Yoshiko Miura, Yuzuru Takamura, Electrochemical assay for saccharide-protein interactions using glycopolymer-modified gold nanoparticles, Electrochemistry Communications, 2011.08, 糖鎖高分子という特殊な素材でコートした金微粒子を用いることにより、糖ータンパク質の相互作用を鋭敏に測定できることを明らかにした。糖とタンパク質の測定は極めて難しいことが知られており、ナノレベルで制御された微粒子と糖鎖多価化合物を使うことによってnM以下での鋭敏な測定を達成した。.
124. T. Fukuda, Y. Inoue, T.Koga, M. Matsuoka, Y.Miura, Encapsulation of Polythiophene by Glycopolymer for Water Soluble Nano-wire, Chemistry Letters, 40, 864, 2011,40,864, 2011.08.
125. Masaya Wada, Yuta Miyazawa, Yoshiko Miura, A specific Inhibitory effect of multivalent trehalose toward amyloid beta (1-40) aggregation, Polymer Chemistry, accepted, 2011.07.
126. Erino Matsumoto, Tomohiro Fukuda, Yoshiko Miura, Bioinert surface to protein adsorption with higher generation of dendrimer SAMs, Colloids and Surfaces B:Biointerfaces, doi:10.1016/j.colsurfb.2011.01.003, 84, 1, 280-284, 2011.05.
127. Jin Ishii, Masayuki Toyoshima, Miyuki Chikae, Yuzuru Takamura, Yoshiko Miura , Preparation of Glycopolymer-modified Gold Nanoparticles and a New Approach for a Lateral Flow Assay, Bull chem Soc Jpn, doi:10.1246/bcsj.2010030, 84, 5, 466-470, selected paper, 2011.05.
128. 三浦 佳子、横山 義之、 柴田 千絵里 , エラスチンモデルペプチドを用いた温度応答性界面の創製と生体機能解析, 高分子論文集, doi:10.1295/koron.67.584, 67, 10, 584, 2010.10.
129. Yoshiko Miura, Hikaru Mizuno, Interaction Analyses of Amyloid beta Peptide (1-40) with Glycosaminoglycan Model Polymers, Bull. Chem. Soc. Jpn, 10.1246/bcsj.20100094, 83 , 9, 1004, 2010, 83(9), 1004-1009, 2010.09.
130. A. Nakano, N. Teramoto, G. Chen, Y. Miura, M. Shibata, Preparation and characterization of complex gel of type I collagen and aluminosilicate containing imogolite nanofibers, J. Appli. Polym. Sci., 118, 2284, 2010, 118, 2284, 2010.09.
131. Tomohiro Fukuda, Erino Matsumoto, Nobuhiko Yui,and Yoshiko Miura, Peculiar Wettability Based on Orientational Change of Self-assembled Hemispherical PAMAM Dendrimer Layer, Chemistry Letters, doi:10.1246/cl.2010.923, 39, 9, 923, 2010, 39, 923-925, 2010.07.
132. T. Fukuda, E. Matsumoto, S. Onogi, Y. Miura, Aggregation of Alzheimer Amyloid β Peptide (1−42) on the Multivalent Sulfonated Sugar Interface, Bioconjugate Chemistry, 10.1021/bc100053x, 21, 6, 1079, 2010, 21, 1079-1086, 2010.06, [URL].
133. Koji Funato, Keiko Fukuda, Yoshiko Miura, Monolayer Formation of hydrocarbons with various reactive groups via photochemical reaction on Si(111)-H surface, Transactions of the Materials Research Society of Japan, 35, 4, 797-800, 2010.04.
134. M. Toyoshima, T. Oura, T. Fukuda, E. Matsumoto, Y. Miura, , Biological specific recognition of glycopolymermodified interfaces by RAFT living radical polymerization, Polymer Journal, doi:10.1038/pj.2009.321, 42, 172, 2010, 42, 172-178, 2010.02.
135. yoshiko miura, Inhibition of protein amyloidosis by glycomaterials, Trends in Glycoscience and Glycotechnology, doi:10.4052/tigg.21.324, 21, 122, 324-334, 2009.12.
136. Tomohiro Fukuda, Shunsuke Onogi, Yoshiko Miura, Dendritic Sugar-Microarrays by Click Chemistry, Thin Solid Films, 518, 880-888, 2009.11.
137. Koji Funato, Naoto Shirahata, Yoshiko Miura, The monolayer of a-Man via Si-C bond formation and protein recognition, Thin Solid Films, 518, 699, 2009.11.
138. D.-H. Yang, R. Katoono, J. Yamaguchi, Y. Miura, N. Yui, Immobilization of polyrotaxane on a solid substrate as the design of dynamic surface, Polymer Jornal, 41, 952-953, 2009.09.
139. Yoshiko Miura, Kiyofumi Yamamoto, Kikuko Yasuda, Yoshihiro Nishida, Kazukiyo koabayashi, Inhibition of Alzheimer Amyloid Aggregation with Sulfate Glycopolymers, Advances in Science and Technology , 57, 166-169, 2009.08.
140. Masayuki Toyoshima, Yoshiko Miura, Preparation of GLycopolymer-Substituted Gold nanoparticles and Their Molecular Recognition, Journal of Polymer Science PartA: Polymer Chemistry, 47, 1412-1421, 2009.03.
141. Erino Matsumoto, Takanori Yamauchi, Tomohiro Fukuda, Yoshiko Miura, Sugar microarray by click chemistry, Sci. Technol. Adv. Mater. , 10, 034605, 2009.03.
142. Miyuki Chikae, Tomohiro Fukuda, K. Kerman, K. Idegami, Yoshiko Miura, Eiichi Tamiya, Amyloid beta-detection with saccharide immobilized gold nanoparticle on carbon electrode, Bioelectrochemistry, 74, 118-123, 2008.11.
143. Yoshiko Miura, Takahiro Yamauchi, Hajime Sato, Tomohiro Fukuda, The Self-Assembled Monolayer of Saccharide via Click Chemistry: Formation and Protein Recognition, Thin Solid Films, 516, 2443, 2008.09.
144. 三浦佳子, 糖質薄膜を用いた生体検出, 表面, 46, 9, 443, 2008.09.
145. 豊島雅幸、大矢健、三浦佳子、小林一清, 糖鎖修飾金微粒子の合成と生体機能解析, 紛体および粉末治金, 54, 843, 2008.09.
146. Yoshiko Miura, Chouga You, Reiko Ohnishi,, Inhibition of Alzheimer amyloid beta aggregation by polyvalent trehalose, Sci. Technol Adv Mat , 9, 24407, 2008.07.
147. Tomohiro Fukuda, Shunsuke Onogi, Yoshiko Miura, Preparation and Properties of Dendritic Sugar Immobilized Surface, Trans. Mat. Res. Soc. Jpn,, 33, 733, 2008.03.
148. Yoshiko Miura, Shunsuke Onogi, Kiyofumi Yamamoto, Synthesis of Glycodendrimer via Click Chemistry and Protein Affinities, Trans. Mat. Res. Soc. Jpn, 33, 729, 2008.03.
149. Yoshiko Miura, Kikuko Yasuda, Kiyofumi Yamamoto, Mihoko Koike, Yoshihiro Nishida, Kazukiyo Kobayashi, Inhibition of Alzhimer Amyloid Aggregation with Sulfated Glycopolymers , Biomacromolecules, 8, 2129, 2007.11.
150. Yoshiko Miura, Synthesis and Biological Application of Glycopolymers, Journal of Polymer Science Part A: Polymer Chemsitry, 45, 5031, 2007.11.
151. Yoshiko Miura, Daisuke Kouketsu, kazukiyo Kobayashi, Synthesis and Properties of a Well-Defined Glycopolymer via Living radical Polymerization, Polymer Advanced Technology, 18, 647, 2007.07.
152. Hajime Sato, Yoshiko Miura, Nagahiro Saito, Kazukiyo Kobayashi, Osamu Takai, Fibroblastic Microfabrication by Molecular Recognition on Substrate, Surface Science, 601, 3871, 2007.04.
153. V. Percec, E. Aqad, M. Peterca, M. R. Imam, M. Glodde, T. K. Bera, Y. Miura, V. S. K. balagurusamy, P. C. Ewbank, H. Wurthner, P. A. Heiney, Self-Assembly of Semifluorinated Minidendrons Attached to Electron-Acceptor Groups into Pyramidal Columns, Chemistry European Journal, 13, 3330, 2007.04.
154. Tetsu Yonezawa, Naoto Shirahata, Yoshiko Miura, Trial of functionalization of silicon tip surface by Si-C bonding., Trans. Mat. Res. Soc Jpn, 32, 767, 2007.03.
155. Hajime Sato, Yoshiko Miura, Nagahiro Saito, Kazukiyo Kobayashi, Osamu Takai, A Micropatterned Multifunctional Carbohydrate Display by an Orthogonal Self-Assembling Strategy, Biomacromolecules, 8, 753-756, 2007.01.
156. Yoshiko Miura, Akio Sakaki, Masamichi Kamihira, Shinji Iijima, Kazukiyo Kobayashi, A globotriaosylceramide (Gb3Cer) mimic peptide , Biochimica et Biophysica Acta, 1760, 883, 2006.09.
157. Hajime Sato, Yoshiko Miura, Takahiro Yamauchi, Kazukiyo , Carbohydrate Microarray by Click Chemistry, Trans. Mat. Res. Soc. Jpn, 31, 659, 2006.04.
158. V. Percec, M. Glodde, M. Peterca, A. Rapp, I. Shnell, H. W. Spiess, T. K. Bera, Y. Miura, V. S. K. Balagurusamy, E. Aqad, P. A. Heiney, Self-Assembly of Semifluorinated Dendrons Attached to Electron-Donor Groups Mediates Their pi-Stacking via a Helical Pyramidal Columns, Chemistry European Journal, 12, 6298, 2006.04.
159. Yoshiko Miura, The Development and the Character of Saccharide Biosensors, Trends in Glycoscience and Glycotechnology, , 18, 349, 2006.04.
160. Yoshiko Miura, Chieri Shibata, Kazukiyo Kobayashi, Theremoresponsive Self-Assembly of Short Elastin-Like Peptides , Trans Mat Res Soc Jpn, 31, 549, 2006.04.
161. Yoshiko Miura, Chieri Shibata, Kazukiyo Kobayashi, Theremoresponsive Self-Assembly of Short Elastin-Like Peptides , Trans Mat Res Soc Jpn, 31, 549, 2006.04.
162. Naoto Shirahata, Atsushi Hozumi, Yoshiko Miura, Kazukiyo Kobayashi, Y. Sakka, T. Yonezawa, An efficient matrix that resists the nonspecific adsorption of protein to fabricate carbohydrate array on silicon , Thin Solid Films, 499, 213, 2006.03.
163. Y. Yamada, Y. Miura, A. Sakaki, T. Yoshida, K. Kobayashi, Design of Multifunctional Peptides expressing both antimicrobial activity and Shiga toxin Neutralizating Activity , Bioorg. Med. Chem, 14, 77, 2006.01.
164. Y. Shingu, A. Miyachi, Y. Miura, K. Kobayashi, Y. Nishida, One-pot a-glycosylation pathway via the Generation in situ of a-glycopyranosyl imidates in N, N-dimethylformamide, Carbohydr. Res. , 340, 2236, 2005.10.
165. Natsuko Wada, Yoshiko Miura, Kazukiyo Koabayashi, Synthesis and Biological Properties of Glycopolymer-Polylactide Conjugate, Trans. Mat. Res. Soc. Jpn, 32, 767, 2005.04.
166. V. Percec, A. Dulcey, M. Peterca, M. Illies, Y. Miura, U. Edlund, P. A. Heiney, Helical Porous Protein Mimics Self-Assembled From Amphiphilic Dendritic Dipeptide, Aust. J. Chem. , 58, 472, 2005.03.
167. V. Percec, A. E. Dulcey, V. S. K. Bulagurusamy, Y. Miura, J. samidrkal, M. Peterca, S. Nummelin, U. Edlund, S. D. Hudson, P. A. Heiney, H. Duan, S. N. Magonov, S. A. Vinogradov, Self-Assembly of Amphiphilic Dendritic Dipeptides into Helical Pores, Nature, 430, 764, 2004.09.
168. Yoshiko Miura, Hajime Sato, Takayasu Ikeda, Hiroyuki Sugimura, Osamu Takai, and Kazukiyo Kobayashi, Micro-patterned Carbohydrate Displays by Self-Assembly of Glycoconjugate Polymers on Hydrophobic Template, Biomacromolecules, 5, 1708, 2004.07.
169. Yoshiko Miura, Natsuko Wada, Yoshihiro Nishida, H. Mori, K. Kobayashi, Chemoenzymatic Synthesis of Glycoconjugate Polymers Starting from Non-reducing Disaccharides, J. Polym. Sci. part A Polym. Chem. 2004, 42, 4598, 42, 4598, 2004.04.
170. Yoshiko Miura, Yuki Sasao, Masamichi Kamihira, Akio Sakaki, Shinji Iijima, Kazukiyo kobayashi, Peptides binding to a Gb3 mimic selected from a phage library, Biochem. Biophys. Acta, 1673, 131, 2004.04.
171. M. Suzuki, Y. Nishida, Y. Ohguro, Y. miura, A. Tsuchida, K. Kobayashi, Synthesis and Characterization of Asymmetric O-and m-nitrobenzoic acids with a 1,3-benzodiooxole skeleton, Tetrahedron Assym, 15, 159, 2004.04.
172. I. Shiyanovskaya, K. D. Singer, V. Percec, T. K. Bera, Yoshiko Miura, M. glodde, Charge Transport in Hexagonal Columnar Liquid Crystal Self-Organized From Supramolecular Cylindrical based on acene-Functionalized Dendron, Phys. Rev. B. , B67, 035204, 2003.04.
173. Y. Miura, T. Ikeda, N. Wada, K. kobayashi, Chemoenzymatic Synthesis of Glycoconjugate Polymers: Greening the Synthesis of biomaterials, Green Chemistry, 5, 610, 2003.04.
174. Y. Miura, T. Ikeda, N. Wada, K. Kobayashi, Chemoenzymatic synthesis of a Multivalent Aminoglycoside, Macromol. Biosci, 3, 362, 2003.04.
175. Naoto Shirahata, Tetsu Yonezawa, Yoshiko Miura, Kazukiyo Kobayashi, K. Koumoto, Patterned Adsorption of Protein onto Carbohydrate Monolayer Immobilized on Si, Langmuir, 19, 9107, 2003.04.
176. Yoshiko Miura, takayasu ikeda, kazukiyo kobayashi, Chemoenzymatically Synthesized Glycoconjugate Polymers, Biomacromolecules, 10.1021/bm025714b, 4, 2, 410, 2003.02.
177. V. Percec, M. glodde, T. K. Bera, Y. Miura, I. shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, L. Schnell, A. Rapp, H. W. Spiess, S. D. Hudson, H. Duan, Self-Organization of Supramolecular Helical Dendrimers into Complex Electronic materials, nature, 419, 384, 2002.04.
178. Yoshiko Miura, Yuuki Sasao, Hirofumi Dohi, Yoshihiro Nishida and Kazukiyo Kobayashi, Self-assembled monolayers of globotriaosylceramide (Gb3) mimics: surface-specific affinity with shiga toxins , doi:10.1016/S0003-2697(02)00318-4, 310, 27, 2002.04.
179. Y. Miura, G.-C. Xu, S. Kimura, S. Kobayashi, M. Iwamoto, Y. Imanishi, J. Umemura, Multilayer Formation of Oriented Helical Peptides Glued by hydrogen Bonding, Thin Solid Films, 393, 59, 2001.04.
180. Y. Miura, S. Kimura, S. Kobayashi, Y. Imanishi, J. Umemura, Cation recognition by self-assembled monolayers of oriented helical peptides having a crown ether unit, Biopolymers, 55, 391, 2000.04.
181. S. Kimura, Y. Miura, T. Morita, S. Kobayashi, Y. Imanishi, Preparation and Functions of Self-Assembled Monoalyers of Helix Peptides, J. Polym. Sci. PartA Polym. Chem. , 38, 4826, 2000.04.
182. Y. Miura, S. Kimura, S. Kobayashi, M. Iwamoto, Y. Imahishi, J. Umemura, Negative Surface potential Produced by Self-Assembled Monoalyers of Helix Peptides Oriented Vertically to a Surface, Chem Phys. Lett, 315, 1, 1999.04.
183. Y. Imanishi, Y. Miura, M. Iwamoto, S. Kimura, J. Umemura, Surface Potential Generation by Helical Peptide Monolayers and Multilayer on Gold Surface, Proc. Jpn Acad Ser B, 75B, 287, 1999.04.
184. Yoshiko Miura, S. Kimura, Y. Imanishi, J. Umemura, Oritented Helical Peptide Layer on the Carbohydrate-Terminated Alkanethiol Immobilized on a Gold Surface, Langmuir, 15, 1155, 1999.01.
185. Y. Miura, S. Kimura, Y. Imanishi, J. Umemura, Formation of Oriented Helical Peptide Layers on a Gold Surface due to the Self-assembling Properties of Peptides, Langmuir, 14, 6935, 1998.04.
186. Y. Miura, S. Kimura, Y. Imanishi, J. Umemura, Self-Assembly of a-helix peptide/crown ether conjugate upon complexation with ammonium-terminated alkanethiolate, 14, 2761, 1998.04.
187. 三浦佳子、木村俊作、今西幸男、梅村順三, 分子認識部位を有するへリックスペプチドの分子集合体の構築, 70, 101, 1998.04.
188. S. Kimura, K. fujita, Y. Miura, G.C. Xu, Y. Muraji, T. Kidchob, Y. Imanishi, Peptide Supramolecules, Curr. Top Peptide Protein Res, 2, 137, 1997.04.
189. Y. Imahisi, K. Fujita, Y. Miura, S. Kimura, Supramolecular Systems Composed of a-Helical Peptides, Supramolecular Sci, 3, 13, 1996.01.

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