Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acsami.4c03805

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

<jats:title>Abstract</jats:title><jats:p>The implementation of polymer brush coatings has proven crucial in biomedical and biotechnological applications for controlling biological interactions. Despite the extensive research and use of synthetic polymer coatings, concerns regarding their long‐term non‐biodegradability have arisen. This issue is significant as non‐degradable polymers can lead to complications such as inflammatory responses and bioaccumulation, highlighting the need for polymers that degrade in a controlled manner. To address this, polyphosphonate brushes are synthesized as anti‐biofouling coatings on silicon surfaces via controlled surface‐initiated organocatalytic ring‐opening polymerization (SI‐ROP) of cyclic phospholanes. 2‐Ethyl‐2‐oxo‐1,3,2‐dioxaphospholane and 2‐hexyl‐2‐oxo‐1,3,2‐dioxaphospholane are chosen as the monomers to prepare hydrophilic and hydrophobic brushes with thicknesses up to 55 nm, with a proven degradability in aqueous media. In addition, protein adsorption, bacterial adhesion, and biofilm formation are investigated as a function of the polyphosphonate side chain. Compared to non‐coated surfaces and polyester brushes, hydrophilic poly(2‐ethyl‐2‐oxo‐1,3,2‐dioxaphospholane) brushes have an enhanced resistance toward fouling of albumin, fibrinogen, and diluted human serum proteins, as well as toward <jats:italic>Escherichia coli</jats:italic> and <jats:italic>Staphylococcus aureus</jats:italic> bacteria. The stability and anti‐biofouling performance of hydrophilic polyphosphonate brushes position them as an attractive option as degradable materials for anti‐biofouling matrices on medical devices and/or lubricious coatings for artificial implant technologies.</jats:p>

DOI： 10.1002/adfm.202316201

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.snb.2024.135882

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

Three-dimensional printing of cell constructs with high-cell density, shape fidelity, and heterogeneous cell populations is an important tool for investigating cell sociology in living tissues but remains challenging. Herein, we propose an artificial intercellular adhesion method using a photoresponsive chemical cue between a thiol-bearing polymer and a methacrylate-bearing cell membrane. This process provided cell fabrication containing 108 cells/mL, embedded multiple cell populations in one structure, and enabled millimeter-sized scaleup. Our approach allows for the artificial cell construction of complex structures and is a promising bioprinting strategy for engineering tissues that are structurally and physiologically relevant.

DOI： 10.1021/acsbiomaterials.3c01987

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Publishing type：Research paper (scientific journal)  

DOI： 10.1039/D3SM01309J

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Authorship：Corresponding author   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.langmuir.3c02696

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.snb.2023.135031

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Authorship：Last author,　Corresponding author   Publishing type：Research paper (scientific journal)  

DOI： 10.1080/09205063.2023.2244737

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Publishing type：Research paper (scientific journal)   Publisher：MDPI AG  

The molecule 2-nonenal is renowned as the origin of unpleasant human aging-related body odor that can potentially indicate age-related metabolic changes. Most 2-nonenal measurements rely on chromatographic analytical systems, which pose challenges in terms of daily usage and the ability to track changes in concentration over time. In this study, we have developed liquid- and gas-phase biosensors (bio-sniffers) with the aim of enabling facile and continuous measurement of trans-2-nonenal vapor. Initially, we compared two types of nicotinamide adenine dinucleotide (phosphate) [NAD(P)]-dependent enzymes that have the catalytic ability of trans-2-nonenal: aldehyde dehydrogenase (ALDH) and enone reductase 1 (ER1). The developed sensor quantified the trans-2-nonanal concentration by measuring fluorescence (excitation: 340 nm, emission: 490 nm) emitted from NAD(P)H that was generated or consumed by ALDH or ER1. The ALDH biosensor reacted to a variety of aldehydes including trans-2-nonenal, whereas the ER1 biosensor showed high selectivity. In contrast, the ALDH bio-sniffer showed quantitative characteristics for trans-2-nonenal vapor at a concentration range of 0.4–7.5 ppm (with a theoretical limit of detection (LOD) and limit of quantification (LOQ) of 0.23 and 0.26 ppm, respectively), including a reported concentration (0.85–4.35 ppm), whereas the ER1 bio-sniffer detected only 0.4 and 0.8 ppm. Based on these findings, headspace gas of skin-wiped alcohol-absorbed cotton collected from study participants in their 20s and 50s was measured by the ALDH bio-sniffer. Consequently, age-related differences in signals were observed, suggesting the potential for measuring trans-2-nonenal vapor.

DOI： 10.3390/s23135857

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/cmdc.202300217

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DOI： 10.1002/jbm.a.37546

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

Polymers for pharmaceutical use have been attractive in medical treatments because of the conjugation of multifunctional components and their long circulation time in the blood stream. Bone-targeted drug delivery systems are also no exceptional, and several polymers have been proposed for the treatment of bone diseases, such as cancer metastasis and osteoporosis. Herein, we report that polyphosphodiesters (PPDEs) have a potential to enhance osteoblastic differentiation, and they have a targeting ability to bone tissues in vivo. Two types of PPDEs, poly (ethylene sodium phosphate) (PEP•Na) and poly (propylene sodium phosphate) (PPP•Na), have been synthesized. Regardless of the alkylene structure in the main chain of PPDEs, the gene expression of osteoblast-specific transcription factors and differentiation markers of mouse osteoblastic-like cells (MC3T3-E1 cells) cultured in a differentiation medium was significantly upregulated by the addition of PPDEs. Moreover, it was also clarified that the signaling pathway related to cytoplasmic calcium ions was activated by PPDEs. The mineralization of MC3T3-E1 cells has a similar trend with its gene expression and is synergistically enhanced by PPDEs with β-glycerophosphate. The biodistribution of fluorescence-labeled PPDEs was also determined after intravenous injection in mice. PPDEs accumulated well in the bone through the blood stream, whereas polyphosphotriesters (PPTEs) tended to be excreted from the kidneys. Hydrophilic PEP•Na showed a superior bone affinity as compared with PPP•Na. PPDEs could be candidate polymers for the restoration of bone remodeling and bone-targeting drug delivery platforms.

DOI： 10.1002/jbm.a.37499

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/admi.202201002

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.langmuir.2c00724

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

DOI： 10.1016/j.biosx.2022.100169

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Japanese Society for Dental Materials and Devices  

DOI： 10.4012/dmj.2021-205

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Publishing type：Research paper (scientific journal)  

DOI： 10.1039/D2BM00885H

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media {LLC}  

<jats:title>Abstract</jats:title><jats:p>Volatile organic compounds (VOCs) released through skin (transcutaneous gas) has been increasing in importance for the continuous and real-time assessment of diseases or metabolisms. For stable monitoring of transcutaneous gas, finding a body part with little interference on the measurement is essential. In this study, we have investigated the possibility of external ears for stable and real-time measurement of ethanol vapour by developing a monitoring system that consisted with an over-ear gas collection cell and a biochemical gas sensor (bio-sniffer). The high sensitivity with the broad dynamic range (26 ppb–554 ppm), the high selectivity to ethanol, and the capability of the continuous measurement of the monitoring system uncovered three important characteristics of external ear-derived ethanol with alcohol intake for the first time: there is little interference from sweat glands to a sensor signal at the external ear; similar temporal change in ethanol concentration to that of breath with delayed peak time (avg. 13 min); relatively high concentration of ethanol relative to other parts of a body (external ear-derived ethanol:breath ethanol = 1:590). These features indicated the suitability of external ears for non-invasive monitoring of blood VOCs.</jats:p>

DOI： 10.1038/s41598-021-90146-1

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

DOI： 10.1021/acs.langmuir.1c02200

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：{SAGE} Publications  

Polymerizable bactericides, such as quaternary ammonium compound–based monomers, have been intensively studied as candidates for immobilizing antibacterial components on dental resin. However, they predominantly exhibit a bacteriostatic behavior, rather than bactericidal, as the immobilized components are left with insufficient molecular movement to disrupt the bacterial surface structure through contact-mediated action. In this study, we developed a novel strategy to increase the density of the immobilized bactericide and enhance its antibacterial/antibiofilm properties by combining a surface-grafting technique with electron beam irradiation. A solution of the quaternary ammonium compound–based monomer, 12-methacryloyloxydodecylpyridinium bromide (MDPB), was coated on polymethyl methacrylate (PMMA) resin specimens at the concentrations of 30, 50, and 80 wt%. The coated resins were subsequently exposed to 10 MeV of electron beam irradiation at 50 and 100 kGy, followed by thermal stabilization at 60 °C. The antibacterial effect was evaluated by inoculating a Streptococcus mutans suspension on the coated PMMA resin samples, which exhibited bactericidal effects even after 28 d of aging (P < 0.05, Tukey’s honestly significant difference test). Transmission electron microscopy and bacteriolytic activity evaluation revealed that the S. mutans cells had sustained membrane depolarization. Furthermore, the antibiofilm effects against S. mutans and bacteria collected from human saliva were assessed. The thickness and the percentage of membrane-intact cells of the S. mutans and multispecies biofilms formed on the MDPB-immobilized surfaces were significantly lower than the uncoated PMMA specimens, even after 28-d aging (P < 0.05, Tukey’s honestly significant difference test). Thus, the immobilization of antibacterial MDPB via electron beam irradiation induced rapid membrane depolarization, increasing membrane permeability and eventually causing cell death. Our strategy substantially enhances the antibacterial properties of the resinous materials and inhibits biofilm formation, therefore demonstrating significant potential for preventing infectious diseases in the oral environment.

DOI： 10.1177/00220345211026569

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Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media {LLC}  

DOI： 10.1038/s41428-021-00548-1

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：{MDPI} {AG}  

Methanol (MeOH) in exhaled breath has potential for non-invasive assessment of intestinal flora. In this study, we have developed a biochemical gas sensor (bio-sniffer) for MeOH in the gas phase using fluorometry and a cascade reaction with two enzymes, alcohol oxidase (AOD) and formaldehyde dehydrogenase (FALDH). In the cascade reaction, oxidation of MeOH was initially catalyzed by AOD to produce formaldehyde, and then this formaldehyde was successively oxidized via FALDH catalysis together with reduction of oxidized form of β-nicotinamide adenine dinucleotide (NAD+). As a result of the cascade reaction, reduced form of NAD (NADH) was produced, and MeOH vapor was measured by detecting autofluorescence of NADH. In the development of the MeOH bio-sniffer, three conditions were optimized: selecting a suitable FALDH for better discrimination of MeOH from ethanol in the cascade reaction; buffer pH that maximizes the cascade reaction; and materials and methods to prevent leaking of NAD+ solution from an AOD-FALDH membrane. The dynamic range of the constructed MeOH bio-sniffer was 0.32–20 ppm, which encompassed the MeOH concentration in exhaled breath of healthy people. The measurement of exhaled breath of a healthy subject showed a similar sensorgram to the standard MeOH vapor. These results suggest that the MeOH bio-sniffer exploiting the cascade reaction will become a powerful tool for the non-invasive intestinal flora testing.

DOI： 10.3390/s21144897

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For understanding the status of intestinal flora non-invasively, methanol (MeOH) has been attracting the attention. In this study, we have developed and compared two different liquid-phase methanol biosensors. One, referred to as the AOD electrosensor, utilized alcohol oxidase (AOD) and an oxygen electrode. It electrochemically measured the decrease in oxygen through AOD-catalyzed oxidation of MeOH. The other, referred to as the AOD-FALDH fluorosensor, exploited a cascade reaction of AOD and formaldehyde dehydrogenase (FALDH) in conjunction with a fiber-optic sensor. It measured increase in the fluorescence from reduced form of β-nicotinamide adenine dinucleotide (NADH) that was a final product of the two-enzyme cascade reaction. Due to the cascade reaction, the AOD-FALDH fluorosensor showed 3 times better sensitivity along with 335 times wider dynamic range (494 nM-100 mM) than those of the AOD electrosensor (1.5-300 μM). The selectivity to MeOH was also improved by the cascade reaction with AOD-FALDH as no sensor output was observed from other aliphatic alcohols than MeOH in contrast to the AOD electrosensor. Although the use of FALDH resulted in the increase in the sensor output from aldehydes, such as acetaldehyde and formaldehyde, considering their concentrations in body fluids, the influence on the sensor output is limited. These results indicate that incorporating the cascade reaction into fluorometry enables enhanced biosensing of MeOH that will be useful for assessment of intestinal flora with little burden.

DOI： 10.1016/j.bios.2021.113136

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

Poly(dimethylsiloxane) (PDMS) is known as one of the most established polymers for making elastomers. Therefore, it is commonly used for the fabrication of biomedical devices. Many PDMS surface modification processes have been proposed recently to increase PDMS reliability in medical fields. However, the modified surface's long-term stability is still limited. Hydrophobic recovery of PDMS is widely recognized as a factor that reduces the efficacy of PDMS surface modification. The photoreactive zwitterionic polymer effectively suppresses the hydrophobic recovery of PDMS, according to the current analysis. The photoreactive zwitterionic monomer, 2-[2-(Methacryloyloxy)ethyldimethylanmmonium] ethyl benzophenoxy phosphate (MBPP) was polymerized by conventional radical polymerization and coated on O2-plasma-treated PDMS specimens. The specimens were immersed in an aqueous solution of 2-methacryloyloxyethyl phosphorylcholine (MPC) and exposed under ultraviolet (UV) radiation for 3 h. Instead, of poly(MBPP) (PMBPP), benzophenone (BP) was also used as a conventional photoinitiator. The time-dependent change in the wettability and elemental composition of the specimen surface was monitored for nine weeks after photo-grafting of poly[2-methacryloyloxyethyl phosphorylcholine (MPC)] (PMPC). The advancing and receding contact angles (θA/θR) of the pristine PDMS specimen were 112°/71° and significantly decreased immediately after the grafting of PMPC regardless of types of photoinitiator. However, the hydrophobicity of the surface gradually recovered, and θA was changed from 12° to 81° for nine weeks of storage under air atmosphere when BP was used as a photoinitiator for graft polymerization of MPC. However, surface hydrophilicity (θA ≅ 20°) of the surface grafted with PMPC with PMBPP as an initiator was effectively preserved for nine weeks. This surface also showed excellent lubricity and non-fouling properties regardless of the storage periods. Therefore, zwitterionic photoreactive polymer, PMBPP, is then used as a macrophotoinitiator for the surface modification of PDMS.

DOI： 10.1016/j.colsurfb.2021.111900

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Natural melanin affects the reflection and absorption of light, and it is known as an important element in producing bright structural colors in nature. In this study, we prepared core-shell particles using a melanin precursor polymer, that is, polytyrosine (PTy), as a shell layer by the oxidative polymerization of tyrosine ethyl ester (Ty) in the presence of cerium oxide (CeO2) core particles. Inspired by skin tanning, irradiating the CeO2@PTy core-shell particles with UV or natural sunlight caused melanization by extending the π-conjugated length of PTy, producing colloidal particles with the ability to absorb light. The pellet samples consisting of CeO2@PTy particles appeared whitish because of multiple scattered light. In contrast, the light absorption capacity of CeO2@PTy UV or CeO2@PTy Sun particles after light irradiation suppressed scattered light, dramatically improving the visibility of the structural color of the pellet samples made from these particles. Thus, a new method has been developed to control the visualization of structural colors to the human eye by irradiating the melanin precursor polymer with light.

DOI： 10.1021/acs.biomac.1c00161

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Informa {UK} Limited  

Phosphorus is a ubiquitous and one of the most common elements found in living organisms. Almost all molecules containing phosphorus in our body exist as analogs of phosphate salts or phosphoesters. Their functions are versatile and important, being responsible for forming the genetic code, cell membrane, and mineral components of hard tissue. Several materials inspired from these phosphorus-containing biomolecules have been recently developed. These materials have shown unique properties at the biointerface, such as nonfouling ability, blood compatibility, lubricity, mineralization induction capability, and bone affinity. Several unfavorable events occur at the interface of materials and living organisms because most of these materials have not been designed while taking host responses into account. These unfavorable events are directly linked to reducing functions and shorten the usable periods of medical devices. Biomimetic phosphorus-containing polymers can improve the reliability of materials in biological systems. In addition, phosphorus-containing biomimetic polymers are useful not only for improving the biocompatibility of material surfaces but also for adding new functions due to the flexibility in molecular design. In this review, we describe the recent advances in the control of biointerfacial phenomena with phosphorus-containing polymers. We especially focus on zwitterioninc phosphorylcholine polymers and polyphosphoesters.

DOI： 10.1080/14686996.2021.1908095

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Biodegradable polyphosphoesters (PPEs) are of increasing interest due to their promising biomedical applications. Polyphosphodiesters (PPDEs), formed by polyphosphotriester (PPTE) dealkylation, have bone-targeting properties in vivo and therefore are promising polymer drug candidates for bone disease treatment. However, their effects on osteoblasts are still unclear. This study prepared two polymer structures, poly(methyl ethylene phosphate) (PMP) and poly(ethylene sodium phosphate) (PEP•Na), as PPTE and PPDE models, respectively, and investigated their effects on mouse osteoblastic cell (MC3T3-E1) differentiation. Results showed that PMP is inert toward osteoblast differentiation. In contrast, PEP•Na enhanced alkaline phosphatase (ALP) synthesis, matrix mineralization, and osteoblast-related gene expression. PEP•Na also enhanced Wnt signaling pathway–dependent Alp expression, in addition to its own internalization into the cytosol during 3 days of differentiation culture. These results showed that dealkylated PPEs are a polymer drug candidate for osteoporosis treatment, not only because of their bone-targeting properties but also because of the controllable effects of bone anabolism via osteoblast differentiation enhancement.

DOI： 10.1016/j.mtla.2020.100977

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

Volatile organic compounds (VOCs) in breath and skin gas are promising samples for non-invasive and simple disease screening and metabolism assessment. In addition, simultaneous measurement of multiple VOCs helps to improve the examination quality and allows for more reliable disease screening and investigation of detailed metabolic pathways. In this study, we have developed a dual-target gas-phase biosensor (bio-sniffer) that allows for measurement of isopropanol (IPA) and acetone vapours, relevant VOCs for lipid metabolisms, by simply exchanging coenzyme solutions. The measurement exploited a reversible redox reaction that was catalysed by secondary alcohol dehydrogenase (S-ADH). IPA/acetone was oxidised/reduced together with reduction/oxidation of a coenzyme, oxidised (NAD+)/reduced (NADH) form of β-nicotinamide adenine dinucleotide, depending on surrounding pH (8.5/7.5). This reaction resulted in producing/consuming NADH which exhibited autofluorescence (λex = 340 nm, λfl = 490 nm), by which IPA/acetone was measured. The characterization of the dual-target bio-sniffer showed the dynamic ranges for IPA and acetone vapour were 3.3–1000 ppb and 13.0–3000 ppb, respectively, which encompasses those in the breath of healthy people (IPA, 10–30 ppb; acetone, 200–900 ppb). Finally, the dual-target bio-sniffer was applied for measurement of IPA and acetone in the breath of healthy people. As with the standard IPA and acetone vapour, intermittent and repeated measurement of both VOCs in the breath was demonstrated. These results indicated that the dual-target bio-sniffer would be a useful tool to assess the lipid metabolism in detail by measuring temporal changes of IPA and acetone concentrations in the breath.

DOI： 10.1016/j.snb.2020.129260

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：{MDPI} {AG}  

<jats:p>Our groups have previously developed a biochemical gas sensor to measure isopropanol (IPA) in exhaled air and have applied it for breath IPA investigation in healthy subjects and diabetes patients. In this study, the original bio-sniffer was modified with a series of components that improved the limit of detection (LOD). First, the modified IPA bio-sniffer used a C8855-type photomultiplier tube (PMT) that performed well in the photon sensitivity at the peak wavelength of nicotinamide adenine dinucleotide (NADH) fluorescence. Second, the multi-core bifurcated optical fiber, which incorporated 36 fibers to replace the previous dual-core type, enhanced the fluorescence collection. Third, the optical fiber probe was reinforced for greater width, and the flow-cell was redesigned to increase the area of the enzyme-immobilized membrane in contact with the air sample. These modifications lowered the detection limit to 0.5 ppb, a significant increase over the previous 1.0 ppb. Moreover, the modified bio-sniffer successfully analyzed the IPA concentration in exhaled air from a volunteer, which confirmed its capability for real-world sample detection. The modified bio-sniffer is more applicable to breath measurement and the detection of other extremely-low-concentration samples.</jats:p>

DOI： 10.3390/s20236827

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier {BV}  

Low-environmental-impact emulsion systems for transdermal drug delivery in topical treatment have gained increasing interest. However, low stability and adverse systemic side effects severely decrease their efficiency. This study proposed a stable oil-in-water (O/W) emulsion loaded with bifonazole (BFZ) as a lipophilic drug stabilized by poly(2-isopropoxy-2-oxo-1,3,2-dioxaphospholane)-modified cellulose nanocrystals (CNC-g-PIPP) as vehicles for topical delivery of lipophilic drugs. We fully characterized stability, BFZ-loaded particle-stabilized emulsions (PEs) for morphology, droplet size, and its distribution. In addition, we evaluated the in vitro drug-releasing capacity and in vitro skin permeation of BFZ in a porcine skin animal model using a side-bi-side® diffusion cell. An O/W BFZ-loaded emulsion stabilized with CNC-g-PIPP particles (BFZ-loaded CP-PE) with a small mean droplet size of 2.54 ± 1.39 μm was developed and was stable for > = 15 days without a significant change in droplet size. The BFZ-loading efficiency in PEs was 83.1 %. BFZ was slowly released over an extended period, and the releasing ratio from BFZ-loaded CP-PE was only 17 % after 48 h. The BFZ-loaded CP-PE showed a ∼4.4-fold increase in BFZ permeation and penetration compared to a conventional surfactant-stabilized emulsion and BFZ control solution. Fluorescence-labeling studies showed that BFZ-loaded CP-PE could well penetrate skin layers from the stratum corneum (SC) to the dermis. In addition, histopathology studies of porcine skin treated with the PE formulation showed an intact SC with unaltered adjacent structures and no observed signs of inflammation. Therefore, the proposed CP-PE shows great potential as a transdermal drug carrier for enhancing lipophilic drug permeation.

DOI： 10.1016/j.colsurfb.2020.111423

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Biomimetic molecular design is a promising approach for generating functional biomaterials such as cell membrane mimetic blood-compatible surfaces, mussel-inspired bioadhesives, and calcium phosphate cements for bone regeneration. Polyphosphoesters (PPEs) are candidate biomimetic polymer biomaterials that are of interest due to their biocompatibility, biodegradability, and structural similarity to nucleic acids. While studies on the synthesis of PPEs began in the 1970s, the scope of their use as biomaterials has increased in the last 20 years. One advantageous property of PPEs is their molecular diversity due to the presence of multivalent phosphorus in their backbones, which allows their physicochemical and biointerfacial properties to be easily controlled to produce the desired molecular platforms for functional biomaterials. Polyphosphodiesters (PPDEs) are analogs of PPEs that have recently attracted interest due to their strong affinity for biominerals. This review describes the fundamental properties of PPDEs and recent research in the field of macromolecular bone therapeutics.

DOI： 10.3390/molecules25030758

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DOI： 10.1039/d0cc90215b

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<p>Visible light-assisted protein patterning on a solid surface was performed with phosphorylcholine (PC) polymers bearing tyrosine residues. Because of the antifouling nature of PC polymers, protein immobilisation was regiospecifically controlled...</p>

DOI： 10.1039/d0cc02092c

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Current chemotherapy methods have limited effectiveness in eliminating bone metastasis, which leads to a poor prognosis associated with severe bone disorders. To provide regional chemotherapy for this metastatic tumor, a bone-targeting drug carrier was produced by introducing the osteotropic bisphosphonate alendronate (ALN) units into an amphiphilic phospholipid polymer, poly(2-methacryloyloxyethyl phosphorylcholine-co-n-butyl methacrylate). The polymer can form nanoparticles with a diameter of less than 30 nm; ALN units were exposed to the outer layer of the particle. A simple mixing procedure was used to encapsulate a hydrophobic anticancer drug, known as docetaxel (DTX), in the polymer nanoparticle, providing a uniform solution of a polymer-DTX complex in the aqueous phase. The complex showed anticancer activities against several breast cancer cell lines, and the complex formation did not hamper the pharmacological effect of DTX. The fluorescence observations evaluated by an in vivo imaging system and fluorescence microscopy showed that the addition of ALN to the polymer-DTX complex enhanced bone accumulation. Bone-targeting phospholipid polymers are potential solubilizing excipients used to formulate DTX and deliver the hydrophobic drug to bone tissues by blood administration.

DOI： 10.1002/jbm.a.36968

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<p>In this study, oligo-prolines, (Pro)n (n=6 and 9) inspired by the backbone structure of collagen, were evaluated as a novel non-ionic anti-fouling peptide. Two oligo-prolines with a cysteine residue were...</p>

DOI： 10.1039/d0tb00051e

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Resin-based reconstructive/restorative materials with antibacterial effects are potentially useful for preventing dental and oral diseases. To this end, the immobilization of an antibacterial component on the surface of a resin by incorporating polymerizable bactericide such as a quaternary ammonium compound-monomer 12-methacryloyloxydodecylpyridinium bromide (MDPB) is an effective technique. However, the effectiveness of immobilized bactericide is reduced by salivary protein coverage. We address this issue by utilizing 2-methacryloyloxyethyl phosphorylcholine (MPC) polymer, which exhibits protein repellency, with MDPB to fabricate a novel copolymer, which served as a surface coating on a methacrylate-based resin. This coating provided a more hydrophilic surface than that provided by MDPB coating and reduced the adsorption of bovine serum albumin and salivary protein. To evaluate bacterial growth on the contact surface, Streptococcus mutans suspension was placed on the coated specimen. After 24-h incubation, MDPB/MPC copolymer exhibited killing effects against S. mutans. Moreover, confocal laser scanning microscopy and scanning electron microscopy were used to evaluate biofilm formation after 48-h incubation in S. mutans suspension, which revealed sparse biofilm and dead bacteria in biofilm on the surface coated with MDPB/MPC. Overall, the proposed surface coating on dental resins exhibited protein-repellent ability and inhibitory effects against bacteria and oral biofilms.

DOI： 10.1002/jbm.b.34661

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© 2020 Elsevier B.V. We developed a biochemical gas sensor (bio-sniffer) using the enzymatic reaction of alcohol dehydrogenase (ADH) to target ethanol in skin gas. By introducing a gas concentrator using liquid nitrogen, we constructed a highly sensitive system for skin gas measurements. The ethanol bio-sniffer was built from an optical-fiber probe employing an ADH enzyme membrane, an UV-LED light source for excitation, and a photomultiplier tube. Ethanol was measured by detecting the autofluorescence of the coenzyme NADH due to the enzymatic reaction of ADH. We established a system for measuring concentrated gases by connecting the sensor with a gas concentrator and introducing concentrated skin gas to the sensing surface. This suppressed diffusion of the concentrated gases to achieve maximum fluorescence intensity by optimizing the measurement system. The calibration curve from obtained peak values showed ethanol gas can be measured over 1–3100 ppb, which included skin gas concentrations during alcohol consumption. Finally, when applied to measurements of ethanol in skin gas following alcohol consumption, the output was found to be dependent on concentration, similarly to using standard gases. Consecutive measurements were possible using periodic sampling with 6-min intervals for 180 min of monitoring. Skin ethanol concentrations rose from 20 min after consuming the alcohol, exhibited a peak value of 25 ppb skin gas ethanol at around 60 min, and gradually declined. Thus, the system can be used for non-invasive percutaneous evaluation of human volatile organic chemicals in blood.

DOI： 10.1016/j.talanta.2020.121187

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society  

For improving lubricity, the formation of zwitterionic polymer brushes on material surfaces is one of the most promising approaches. In this study, the photoreactive zwitterionic monomer 2-[2-(methacryloyloxy)ethyldimethylanmmonium] ethyl benzophenoxy phosphate (MBPP) was synthesized to improve the stability of zwitterionic polymer brushes. Although MBPP contains a benzophenone moiety in this molecule, it is water-soluble because of the zwitterionic linker. As a substrate, poly(ether ether ketone) (PEEK) was selected because it has recently been used to replace metals in orthopedic implants. Furthermore, PEEK is photosensitive, and UV graft polymerization of (meth)acrylic monomers on the surface can be performed without using any photoinitiators. Aqueous solutions containing various molar ratios of 2-(methacryloyloxy)ethyl phosphorylcholine (MPC) and MBPP were prepared, and the PEEK specimens were immersed in these solutions. UV light was used to irradiate the solutions for 180 min, and the formation of grafting layers of zwitterionic polymers on PEEK specimens was confirmed using contact angle measurement and X-ray photoelectron spectroscopy. The surface friction of PEEK was effectively reduced via the photopolymerization of zwitterionic monomers. However, the surface lubricity of poly(MPC) (PMPC)-grafted surface deteriorated during continuous friction because of the removal of PMPC from the surface. Nevertheless, the stability of polymer brushes was effectively improved by adding only 0.5-0.75 mol % of MBPP in the monomer solution. Moreover, the reduction of wear on the surface was determined using confocal laser microscopy. The excellent lubrication phenomenon was attributed to preserving the hydration state of grafted polymers under compressive stress. Moreover, bacterial adhesion on substrates was tested and observed on a neat PEEK and scratched regions of uncross-linked PMPC-grafted PEEK. Note that bacterial adhesion was completely suppressed on the surface of PEEK modified with cross-linked PMPC brushes with MBPP. Thus, we conclude that the surface modification of PEEK with MPC and MBPP can provide ideal surface properties for orthopedic devices.

DOI： 10.1021/acsabm.9b01040

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.190709

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

Particle-stabilized emulsion systems have been developed to address the problematic properties of conventional surfactants. However, the nature and properties of the fine particles used in such systems remain a critical issue for stability enhancement. Herein, we describe a thermoswitchable oil-in-water (O/W) particle-stabilized emulsion that exhibits improved stability due to the addition of cellulose nanocrystals (CNCs) modified with poly[2-isopropoxy-2-oxo-1,3,2-dioxaphospholane] (PIPP), which exhibits relatively good biocompatibility and biodegradability. Various parameters, such as surface activity, concentration of particles, polarity of solvents, and temperatures, on the formation of emulsions with CNCs grafted with PIPP (CNC-g-PIPP) were investigated. Results showed that the surface activity of CNC-g-PIPP was significantly improved compared with the unmodified material. Heptane-in-water particle-stabilized emulsions with CNC-g-PIPP were stably formed, and the effect of temperature on the stability of the emulsions was characterized. CNC-g-PIPP exhibited function as an effective particulate emulsifier at 4 °C because of the strong adsorption at the oil-water interface. However, the emulsions rapidly disintegrated at 45 °C, which is above the low critical solution temperature of PIPP on CNC, as the hydrophobized CNC-g-PIPP desorbed from the oil-water interface. Based on these findings, a thermally induced reversible emulsification/demulsification was presented. The resulting switchable particle-stabilized emulsion based on CNC-g-PIPP shows promise for the ability to control the stability of an emulsion in response to temperature, which is attractive for use in biological applications.

DOI： 10.1021/acs.langmuir.9b01584

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/mame.201900286

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Language：English   Publishing type：Research paper (scientific journal)  

Poly(ether ether ketone) (PEEK) is an alternative material to metals for orthopedic applications. However, the compatibility of PEEK with hard tissues needs to be improved. To address this issue, this study proposes a novel technique for PEEK surface modifications. A polyphosphodiester macromonomer (PEPMA·Na) was synthesized via the demethylation of polyphosphotriester macromonomer obtained via the ring-opening polymerization of cyclic phosphoesters using 2-hydroxypropyl methacrylamide as the initiator. The surface modification of PEEK was performed via photoinduced and self-initiated graft polymerization of PEPMA·Na without using any photoinitiators. The amount of phosphorus due to poly(PEPMA·Na) immobilized on PEEK increased with an increase in the photoirradiation time. The PEEK surface turned hydrophilic due to poly(PEPMA·Na) grafting, with almost similar advancing and receding contact angles, implying that the modified PEEK surface (PEEK-g-poly(PEPMA·Na)) was homogeneous. Specimens were mineral coated by simple static soaking in ×1.5 simulated body fluid (1.5SBF) and by an alternative process that included additional soaking steps in 200 mM CaCl2 aq. and 200 mM K2HPO4 aq. before static soaking in 1.5SBF. Specimens were immersed in 1.5SBF for 28 days in simple static soaking, after which the PEEK-g-poly(PEPMA·Na) surface was completely covered with spherical cauliflower-like mineral deposits that resembled octacalcium phosphate (OCP). Their structural similarities were confirmed via X-ray diffraction (XRD), energy dispersive X-ray spectrometry (EDS), and X-ray fluorescence (XRF) analyses. However, these mineral deposits were not observed on the bare PEEK surface. Due to the additional soaking steps (alternative soaking) undertaken before the static soaking of the specimens in 1.5SBF, the mineral coating on the PEEK-g-poly(PEPMA·Na) was dramatically accelerated and the surface was fully covered with mineral deposits in only one day of soaking. The mineral deposits resulting from both the soaking processes had similar structures. Compared with bare PEEK, osteoblastic MC3T3-E1 cells proliferated more actively on mineral-coated PEEK-g-poly(PEPMA·Na). Thus, the surface immobilization of poly(PEPMA·Na) on a PEEK surface is effective for mineral coating and may be useful to provide hard-tissue compatibility on PEEK.

DOI： 10.1080/09205063.2019.1595305

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.jiec.2019.03.010

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Language：English   Publishing type：Research paper (scientific journal)  

Protein therapeutics has recently attracted interest in various medical treatments. However, the structure and function preservation in proteins under physiological conditions is still an important issue and reliable immobilization techniques are required. In this study, the thermally assisted complexation of proteins with amphiphilic polyphosphoesters is proposed as a new methodology for their durability improvement. Amphiphilic cholesterol-terminated poly(ethylene sodium phosphate) (CH-PEP·Na) was synthesized via the organocatalytic ring-opening polymerization of 2-methoxy-2-oxo-1,3,2-dioxaphospholane initiated by cholesterol as the hydrophobic molecule and followed by demethylation and neutralization. For the protein nanocarrier preparation, a complex of the amphiphilic CH-PEP·Na with bovine serum albumin (BSA) was formed through the hydrophobic interactions between the lipophilic moieties of the protein and the cholesteryl groups of the CH-PEP·Na chains, which were induced by thermal treatment at 90 °C. The resulting complex size ranged between 27 and 51 nm, as confirmed by dynamic light scattering. The complexes dispersed in an aqueous medium exhibited a high stability in size for up to 1 month of storage. CH-PEP·Na efficiently inhibited the thermal aggregation and sedimentation of BSA, unlike poly(ethylene sodium phosphate) (PEP·Na) and cholesterol-terminated poly(ethylene glycol) (CH-PEG). In addition, CH-PEP·Na was able to protect the complexed BSA against proteolytic digestion and the BSA-CH-PEP·Na complexes well adsorbed onto hydroxyapatite even in the presence of BSA (5.5 g/dL). Hence, thermally induced protein-CH-PEP·Na complexes can be a potential tool for the development of bone and dental applications.

DOI： 10.1021/acsomega.8b03585

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Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

DOI： 10.1021/acs.langmuir.8b01007

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DOI： 10.1038/s41428-018-0110-2

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DOI： 10.1021/acs.langmuir.8b04183

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Language：Japanese   Publisher：日本バイオマテリアル学会  

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Language：Japanese   Publisher：(NPO)日本歯周病学会  

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DOI： 10.1021/acs.langmuir.8b00563

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Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry ({RSC})  

DOI： 10.1039/C7BM00930E

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DOI： 10.1016/j.bios.2018.09.070

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：National Institute of Informatics  

To improve the degradability and operability of conventional bone graft materials, we fabricated a water-oil emulsion based on α-tricalcium phosphate (α-TCP) bone paste. Simvastatin, a lipophilic hyperlipidemia treatment agent, reportedly enhances the expression of bone morphogenetic protein- 2 and subsequent bone formation. Accordingly, we assessed the bone forming effects of α-TCP bone-paste containing simvastatin in rat cranial bone defects. Bone paste exhibited porous structure and generation of hydroxyapatite after solidification. X-ray image analysis and histological examination were carried out after implantation of bone paste into rat skull defect. The results showed that new bone was formed after implantation of bone paste containing simvastatin. In particular, bone volume in the 0.1 mg simvastatin group was significantly promoted when compared to controls (no implantation). No bone paste residue was observed in the bone defect at 4 weeks after surgery. Therefore, α-TCP bone paste containing simvastatin is degradable and beneficial for bone tissue engineering.

DOI： 10.11344/nano.9.69

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DOI： 10.1038/s41428-018-0026-x

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DOI： 10.1021/acssensors.7b00865

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

Antigen-presenting cells play a dominant role in cancer immunotherapy. Tumor cells, however, can still resort to several mechanisms of immune evasion that ultimately lead to the development of tumor tissues. In the current study, we performed surface modification of live macrophages with nucleic acid aptamers with the aim to enhance their affinity for tumor cells. Intercellular adhesion of tumor cells to surface-modified macrophages and the functions of the macrophages when in contact with tumor cells were investigated. To immobilize thiol-terminated nucleic acid aptamers that showed high affinity for the membrane protein of the tumor cells, methacryloyl groups were delivered into the sialic acids of the macrophages via metabolic glycoengineering (MGE). The proposed surface modification was cytocompatible and did not induce any undesirable activation of macrophages. According to the cell proliferation assay, the density of aptamers immobilized on a macrophage was found to decrease over time. However, the presence of aptamers on the cell surface was observed for more than 24 h after the immobilization. The number of adherent tumor cells on aptamer-immobilized macrophages was significantly larger than that of non-immobilized macrophages. Although the number of adherent tumor cells on aptamer-immobilized macrophages was not influenced by the pretreatment of doxorubicin to induce apoptosis in tumor cells, the apoptosis-induced tumor cells were highly phagocytosed by the aptamer-immobilized macrophages. The secretion amount of proinflammatory cytokines (TNF-α and IL-12) from the macrophages was coincident with the phagocytic index, which increased with the phagocytic uptake of tumor cells by the macrophages. In addition, the expression level of the major histocompatibility complex (MHC) class I and II molecules, required for antigen presentation, increased in nucleic acid aptamer-immobilized macrophages. Overall, the surface modification of macrophages with nucleic acid aptamers improved the tumor cell recognition of macrophages, indicating that the combination of cell surface engineering and anticancer drug treatment could constitute a promising strategy for tumor cell elimination.

DOI： 10.1021/acs.bioconjchem.8b00793

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DOI： 10.1080/09205063.2017.1366251

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DOI： 10.1016/j.colsurfb.2017.02.015

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DOI： 10.1021/acs.analchem.7b03191

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DOI： 10.1295/koron.2016-0067

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DOI： 10.1021/acssensors.7b00184

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DOI： 10.1021/acs.langmuir.7b00463

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DOI： 10.1016/j.bios.2016.12.050

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Language：Japanese  

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Language：English   Publishing type：Part of collection (book)   Publisher：Elsevier Inc.  

Control of cell surface nanoarchitectures has attracted attention as a process that can be used in both basic research and for therapeutic applications. This chapter summarizes new strategies for the surface modification of living cells with synthetic polymers and the biointerfacial aspects of such immobilized polymers. In particular, N-methacryloyl mannosamine was synthesized as an artificial precursor of sialic acid, placed in contact with human cells, and incubated. Confirmation of delivery of the methacryloyl groups to carbohydrates on cell surfaces was obtained using a thiol-ene reaction. Various thiol-terminated polymers were covalently immobilized and unnatural functions were introduced to cell surfaces while preserving cell viability.In addition to the thiol-ene reaction, methacryloyl-functionalized carbohydrates were also polymerized via conventional free-radical polymerization. The obtained synthetic hydrogels with embedded glycoproteins were able to bind to selectins expressed on endothelial cells, indicating that the glycoproteins transferred to the hydrogels preserved their function. Selectin-mediated interaction is considered an essential step in the progression of various diseases
therefore, hydrogels with embedded glycoproteins may be useful in therapeutic and diagnostic applications.Metabolic delivery of methacryloyl groups to the carbohydrates on mammalian cells is a robust technique for cell surface immobilization and provides a means for both controlling cell functions and synthesizing bioactive polymeric materials.

DOI： 10.1016/B978-0-323-37127-8.00015-7

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DOI： 10.1016/j.talanta.2016.06.036

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DOI： 10.1016/j.colsurfb.2015.12.037

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DOI： 10.1111/eos.12235

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DOI： 10.1016/j.actbio.2015.12.016

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DOI： 10.1038/pj.2016.60

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DOI： 10.1016/j.actbio.2016.03.023

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DOI： 10.1021/acs.biomac.6b00641

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DOI： 10.1021/acs.langmuir.5b02727

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DOI： 10.1021/acs.bioconjchem.6b00455

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DOI： 10.1021/acs.jpcc.5b03934

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DOI： 10.1039/c5ra08843g

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DOI： 10.1016/j.colsurfb.2014.12.003

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DOI： 10.1177/0022034515589282

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DOI： 10.1002/mabi.201500166

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DOI： 10.1039/c5cc06211j

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DOI： 10.1021/acs.jpcb.5b03787

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Language：Japanese   Publisher：日本バイオマテリアル学会  

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Other Link： http://search.jamas.or.jp/link/ui/2014307785

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DOI： 10.1021/cm500260z

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DOI： 10.1080/09205063.2014.911570

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DOI： 10.1002/jbm.a.34321

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Language：Japanese   Publishing type：Research paper (bulletin of university, research institution)  

J-GLOBAL

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DOI： 10.1088/1468-6996/13/6/064101

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DOI： 10.1038/pj.2011.94

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<p>It is essential to investigate the tribological maturation of tissue engineered cartilage that is to be used in medical applications. The friction properties of tissue engineered cartilage have been measured using flat counter surfaces such as stainless steel, glass or ceramics. However, the measured friction properties were significantly inferior to those of natural cartilage, likely because of cartilage adhesion to the counter surface. In this study, a poly(2-methacryloyloxyethyl phosphorylcholine (MPC)) grafted surface is proposed as an appropriate counter surface for cartilage friction evaluation due to the material's ability to reduce the adhesion and reproduce natural tribological conditions. The poly(MPC) grafted surfaces were prepared by atom transfer radical polymerization (ATRP). The friction coefficients for natural cartilage that were measured on the poly(MPC) grafted surface were lower than 0.01 at the sliding velocities of 0.08 and 0.008 mm/s, which is equivalent to that for natural cartilage-on-cartilage. The friction coefficients for the tissue engineered cartilage were reduced with cultivation time at low sliding velocities. Thus it is suggested that the propose

DOI： 10.2495/TD120081

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DOI： 10.1007/s10544-011-9530-x

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DOI： 10.1016/j.colsurfb.2007.10.018

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DOI： 10.1016/j.msec.2006.03.007

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DOI： 10.1021/ma0715573

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DOI： 10.4028/www.scientific.net/AMR.15-17.205

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DOI： 10.1021/la702741q

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Polymeric nanoparticles were prepared by a hydrazide-functionalized MPC polymer (PMBH) as an emulsifier. The human cervical adenocarcinoma (HeLa) cells having noncanonical carbohydrates were prepared by N-levulinoylmannosamine (ManLev) treatment and used as the target cells. The PMBH nanoparticles can adsorb doxorubicin on their surfaces through hydrophobic interaction. When the PMBH/DOX nanoparticles were in contact with ManLev-treated HeLa cells, the number of living cells was dramatically decreased. However, there was little cytotoxicity to native cells without noncanonical carbohydrates on their surface.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

There has been a great deal of interest in polyphosphates, which are biodegradable through hydrolysis and possibly through enzymatic digestion of phosphate linkages under physiological conditions. We have synthesized polyphosphoesters conjugated with oligopeptides as novel bioactive polymer materials. 2-Ethyl-2-oxo-1,3,2-dioxaphospholane(EP) and 2-propargyl-2-oxo-1,3,2- dioxaphospholane(PGP) were copolymerized by ring-opening polymerization. Peptides were immobilized with polyphosphoesters through the click chemistry. The composition of peptides in a polymer was varied with changing in the fraction of PGP.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Well-defined block copolymer brushes consisting of MPC and GMA were prepared on silicon substrates by atom transfer radical polymerization. The polymer thickness was controlled by the polymerization time. The pyridyl disulfide moieties were introduced into the block copolymer brushes via reaction with epoxy group in GMA units. The amount of pyridyl disulfide moieties could be controlled by changing the density and the thickness of polymer brushes. Furthermore, Fab'-fragment which has thiol groups in opposite side of antigen binding domain reacted with block copolymer brushes with pyridyl disulfide moieties. The activity of Fab' fragment will be discussed.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

In order to improve the biocompatibility of segmented polyurethane (SPU) which has been widely used as a biomedical material, the synthesis of segmented poly(urethane-urea) containing phosphorylcholine (PC) moiety (SPUU) was carried out by using aromatic diamine compound with PC unit as a monomer. The obtained poly(urethane-urea) was soluble in aprotic polar solvents such as NMP, DMSO and DMF, but insoluble in water, alcohol and other organic solvents. It was confirmed from the results of blood contacting experiments that the polymer exhibited the excellent biocompatibility, even though the PC content was around 10 mol%, as compared with polyurethane without PC unit. From the results of stress-strain measurements, SPUU membranes exhibited the elastomeric mechanical properties similar to those of SPU.

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DOI： 10.1002/app.24676

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DOI： 10.1002/jbm.a.30820

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DOI： 10.1016/j.bios.2006.05.006

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Publisher：Transactions of the Materials Research Society of Japan, Vol 31, No 4  

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DOI： 10.1016/j.biomaterials.2005.09.041

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Language：English   Publisher：Japan Prosthodontic Society  

<b>Purpose:</b> The aim of the present study was to develop a new and simple method using PMB to prevent plaque colonization on denture surfaces.<br><b>Methods:</b> PMB polymerized with MPC polymer and BMA was prepared as a coating material. Water-insoluble PMB composed of 30 mol% MPC units (PMB30), water-soluble PMB composed of 80 mol% MPC units (PMB80) and clear PMMA disks were prepared. The PMMA disks were dip-coated in 0.5 wt% PMB30 solution or 0.5 wt% PMB80 solution. To examine the PMB coatings' durability, the PMB-coated disks were immersed in distilled water. The PMB elution ratio was measured using a phosphorus analysis. To evaluate the effect of the PMB coating on <i>Candida albicans</i> (<i>C. albicance</i>) adhesion, PMB-coated and uncoated disks were cultured in a solution containing <i>C. albicans</i> for 48 hours. Half of the disks in each group were not washed, and the remaining disks were washed with distilled water to examine the effect of washing. All the PMMA disks were observed and photographed, and the resulting images were analyzed using imaging analysis software.<br><b>Results:</b> In the first 48 hours, approximate 14 % of the PMB30-coating and 12 % of the PMB80-coating were eluted into the distilled water. The adhesion of <i>C. albicans</i> to the PMB30-coated or the PMB80-coated PMMA disks was significantly reduced in both the washed and unwashed groups, compared with the uncoated control disks.<br><b>Conclusion:</b> PMB coating prevents the adhesion of <i>C. albicans</i> to PMMA.

DOI： 10.2186/prp.5.21

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Other Link： http://search.jamas.or.jp/link/ui/2006295822

Publishing type：Research paper (scientific journal)  

DOI： 10.1021/bm050917w

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DOI： 10.1254/jphs.FP0060062

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DOI： 10.1016/j.colsurfb.2006.04.006

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Well-defined block polymer brushes consisting of MPC and GMA (PMPC-b-PGMA brushes) were prepared on silicon substrates via ATRP. The pyridyl disulfide moieties were introduced into the block polymer brushes through the reaction with epoxy group in GMA units. The amount of pyridyl disulfide moieties could be controlled by changing the density and the thickness of polymer brushes. Fab'-fragment which has thiol groups in opposite side of antigen binding domain was reacted with block polymer brushes with pyridyl disulfide moieties and analyzed by X-ray photoelectron spectroscopy (XPS). In PMPC-b-PGMA brushes, N1s, signal at the binding energy of about 400 eV and 403 eV was observed. These signals could be attributed to the amine group in Fab'-fragment and the choline group in MPC unit, respectively. While in PMPC brushes, there was only a signal at the binding energy of about 403 eV. Furthermore, S 2p signal was observed in PMPC-i-PGMA brushes and not in PMPC brushes. From these results, it was confirmed that Fab'-fragment could be covalently immobilized via thiol-disulfide exchange. The activity of antibody against antigen will be reported.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

In natural environment, carbohydrates on the cell surface contribute to most communications between the cell and its environments. 2- Methacryloyloxyethyl phosphorylcholine (MPC) polymers exhibit a surface property that resists nonspecific protein adsorption and cell adhesion, i.e., "biofouling". It was then hypothesized that carbohydrate- immobilization on a MPC polymer surface might be promising way to control protein/material or cell/material interactions. The copolymerization of MPC, n-butyl methacrylate (BMA), and 2-lactobionamidoethyl methacrylate (LAMA) was carried out by radical polymerization. Human hepatocellular liver carcinoma cell line (HepG2) cells were seeded onto polymer films ,and cultured in for 24 and 96 hours. Proliferative ratio (24h-96h culture) was increased with an increase in a LAMA composition of copolymers . Moreover, the ratio on copolymers having 3.0 mol % LAMA unit became about twice compared with that on PBMA. This result indicates that chemistry structure of a substrate influenced adhesion and proliferation of HepG2.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Recently, 2-methacryloyloxyethyl phosphorylcholine (MPC) polymer has been reported as an ideal biocompatible material. In this study, in order to develop the durability of PC-containing polymer, the synthesis of novel aromatic diamine compounds containing phosphorylcholine (PC) group with different spacer structures was carried out to prepare aromatic polyamides with PC moiety. The obtained polyamide had a large molecular weight, and the tough membrane was obtained by solvent casting method. In case of the homopolymer membrane surface, the XPS signal was observed in the P2p region which was derived from the PC group. Therefore, these polyamides exhibited biocompatibility, which would be due to the surface derived from the PC side chain.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

In living system, carbohydrates on the cell surface contribute to most communications between the cell and its environments. 2-Methacryloyloxyethyl phosphorylcholine (MPC) polymers exhibit a surface property that resists nonspecific protein adsorption and cell adhesion, i.e., "biofouling". It was then hypothesized that carbohydrate-immobilization on a MPC polymer surface might be promising way to control protein/material or cell/material interactions. The copolymerization of MPC, n-butyl methacrylate (BMA), and 2-lactobionamidoethyl methacrylate (LAMA) was carried out by radical polymerization. Human hepatocellular liver carcinoma cell line (HepG2) cells and mouse fibroblast (NIH-3T3) cells were seeded onto polymer films, and cultured in for 24, 96, and 168 hours. On PMBL surface, the density of adherent HepG2 cells having asialoglycoprotein receptors was significantly higher than that on poly(MPC-co-BMA) due to ligand/receptor interaction.

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<p>In order to improve the biocompatibility of segmented polyurethane (SPU) which has been widely used as a biomedical material, the synthesis of segmented poly(urethane-urea) containing phosphorylcholine (PC) (SPUU) moiety was carried out by using aromatic diamine compound with PC unit as a monomer. The obtained poly(urethane-urea) was soluble in aprotic polar solvents such as NMP, DMSO and DMF, but insoluble in water, alcohol and acetone. In addition, it was confirmed from the results of blood contacting experiments that the polymer exhibited the excellent biocompatibility, even though the PC content was around 10 mol%, as compared with polyurethane without PC unit. From the results of stress-strain measurements, SPUU membranes exhibited the excellent mechanical properties, where the mechanical properties of SPUU were almost as same as those of SPU.</p>

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<p>Recently, 2-methacryloyloxyethyl phosphorylcholine (MPC) polymer has been reported as an ideal biocompatible material. In this study, in order to develop the durability of MPC polymer, the synthesis of a novel aromatic diamine compound containing phosphorylcholine (PC) group was carried out to prepare aromatic polyamides with PC moiety. The obtained polyamides exhibited biocompatibility, however, XPS signals in the P_2P region were hardly observed on the film surface. Therefore, it was found that PC units were scarcely concentrated on the surface of polymer membrane in such aromatic polyamides because of the rigid main chain structure.</p>

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Language：English   Publisher：Tokyo Medical and Dental University  

The ideal dressing material is bio-inert andkeeps the wound site moist. It is equally importantthat no regenerative tissue is peeled off on theremoval of the dressing. 2-Methacryloyloxyethylphosphorylcholine (MPC) has a phospholipidpolar group that mimics a biomembrane. We preparedpoly [MPC-co-n-dodecyl methacrylate(DMA)] (PMD), using conventional radical polymerizationwith 2,2'-azobisisobutyronitrile as an initiator,and coated it on polyurethane (PU;Tecoflex^&reg; 60 Thermedics Inc.) membrane. Fullthicknesssurgical wounds were made on the dorsalskin of rats and wound healing was comparedunder the following three conditions: air-exposedcontrol (no dressing), PU dressing, and PMDdressing. At 3, 4 and 7 days after the operation, thewound sizes of the PMD dressings were smallerthan the non-dressed wound, and at 6 and 7 daysafter the operation, the wound sizes of PU dressingwere smaller than that of the air-exposed group.But there were no significant difference betweenthe PMD dressing group and PU dressing group.Histologically, scab formation was not observed onthe PU or PMD-dressed wounds. However, in theair-exposed control, a scab was formed and reepithelializationof the wound site was prevented.Additionally, no damage was observed in the histologicalsection of PMD dressed wound after thewound was cured. These results indicate thatPMD dressing (PMD-coated PU membrane) hasthe potential to provide an inert environment forwound healing as well as PU.

DOI： 10.11480/jmds.520203

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Other Link： http://search.jamas.or.jp/link/ui/2006247811

Publisher：Transactions of the Materials Research Society of Japan, Vol 30, No 4  

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DOI： 10.1021/bc049707r

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DOI： 10.1002/jbm.a.30302

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DOI： 10.1016/j.biomaterials.2005.01.049

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DOI： 10.1016/j.colsurfb.2004.12.002

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DOI： 10.1016/j.memsci.2004.10.006

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DOI： 10.1089/ten.2005.11.1658

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Language：English   Publishing type：Research paper (scientific journal)  

The ideal dressing material is bio-inert and keeps the wound site moist. It is equally important that no regenerative tissue is peeled off on the removal of the dressing. 2-Methacryloyloxyethyl phosphorylcholine (MPC) has a phospholipid polar group that mimics a biomembrane. We prepared poly [MPC-co-n-dodecyl methacrylate (DMA)] (PMD), using conventional radical polymerization with 2,2'-azobisisobutyronitrile as an initiator, and coated it on polyurethane (PU
Tecoflex ® 60 Thermedics Inc.) membrane. Full-thickness surgical wounds were made on the dorsal skin of rats and wound healing was compared under the following three conditions: air-exposed control (no dressing), PU dressing, and PMD dressing. At 3, 4 and 7 days after the operation, the wound sizes of the PMD dressings were smaller than the non-dressed wound, and at 6 and 7 days after the operation, the wound sizes of PU dressing were smaller than that of the air-exposed group. But there were no significant difference between the PMD dressing group and PU dressing group. Histologically, scab formation was not observed on the PU or PMD-dressed wounds. However, in the air-exposed control, a scab was formed and re-epithelialization of the wound site was prevented. Additionally, no damage was observed in the histological section of PMD dressed wound after the wound was cured. These results indicate that PMD dressing (PMD-coated PU membrane) has the potential to provide an inert environment for wound healing as well as PU.

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DOI： 10.1002/mabi.200500051

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DOI： 10.1021/bm050156x

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Language：English   Publishing type：Part of collection (book)   Publisher：Elsevier Ltd.  

DOI： 10.1533/9781845690809.3.389

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DOI： 10.1007/s00216-004-2805-9

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DOI： 10.1007/s10047-005-0308-x

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Polymeric nanoparticles (∼200 nm in diameter) coated with 2-methacryloyloxyethyl phosphorylcholine (MPC) copolymers having hydrazide groups were prepared to develop novel drug carriers, which can react with carbohydrates of a specific cell. The Z-potential of the nanoparticles was approximately zero. When the nanoparticles were incubated with the human cervical adenocarcinoma (HeLa) cells expressing N-levulinoyl sialic acid (SiaLev) moiety on membrane proteins, the nanoparticles attached on the cell surface. However, the nanoparticles did not interact with native HeLa cells (non-SiaLev).

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

In order to improve the biocompatibility of segmented polyurethane which has been widely used as a biomedical material, the synthesis of poly(urethane-urea) containing phosphorylcholine (PC) moiety was carried out by using aromatic diamine compound with PC unit as a monomer. The obtained poly(urethane-urea) was soluble in aprotic polar solvents such as NMP, DMSO and DMF, but insoluble in water, alcohol and acetone. In addition, it was confirmed from the results of blood contacting experiments that the polymer exhibited the excellent biocompatibility, even though the PC content was around 10 mol%, as compared with polyurethane without PC unit.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Well-defined block polymer brushes consisting of MPC and GMA were fabricated on silicon substrates by ATRP. 3-(2-bromoisobutyryl) propyldimethylchlorosilane (BDCS)-modified silicon substrates were applied for ATRP of MPC using Cu(I)Br and 2,2'-Dipyridyl (bpy) for 3h. Then, GMA was polymerized from poly(MPC)(PMPC) brush using Cu(I)Br and bpy at ambient temperature. Semilogarithmic plot of monomer concentration was linear with polymerization time. This suggests that the concentration of radicals was constant during the polymerization. The PGMA brush thickness increased linearly with polymerization time. The C/O ratio of the PMPC-b-PGMA block polymer brush surfaces determined by X-ray photoelectron spectroscopy (XPS) became similar to that of the GMA molecule (C/O=2.3) at longer polymerization time. And the water contact angle of PMPC brush increased after block polymerization of GMA. These results indicated that GMA was polymerized from the terminal of PMPC brushes. The pyridyl disulfide group for immobilization of thiol containing biomolecules was also introduced via reaction with epoxy group.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Polymeric materials containing a phosphorylcholine (PC) group has been known to show the improved biocompatibility, which can be used for biomedical field. In this work, a novel aromatic carboxylic acid compound containing PC group (CPC) was synthesized, in order to introduce the PC group into the polymers containing hydroxyl or amino group by polymer reactions. The reaction between CPC and ethyl cellulose was carried out using DCC as a condensation reagent to obtain ethyl cellulose partially substituted with PC group. The chemical structure of the obtained cellulose was confirmed by 1H-NMR and FT-IR, and the elements of PC group were observed on the film surface by XPS analysis.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Porous phosphorylcholine hydrogels cross-linked methacryloyl-functionalized polyphosphates were prepared by copolymerization with 2-methacryloyloxyethyl phosphorylcholine (MPC). To control porous structures of hydrogels, salt-leaching and gas-foaming techniques were applied. The structures of freeze-dried hydrogels were observed by SEM and the pore sizes in hydrogels were well controlled by the above techniques. The degradation of hydrogels depended on the rate of hydrolysis of polyphosphates. The mechanical properties of hydrogels were determined torsional mechanical analysis. The elastic modulus of hydrogels was increased with an increase in the cross-link density. Incorporation of cells in porous hydrogels and the effect of a hydrogel on cell viability will be discussed.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Well-defined block polymer brushes consisting of MPC and GMA were fabricated on silicon substrates by ATRP. 3-(2-bromoisobutyryl) propyldimethylchlorosilane (BDCS) was immobilized on silicon substrates. BDCS-modified silicon substrates were applied for ATRP of MPC using Cu(I)Br, 2,2'-Dipyridyl (bpy) via aqueous and alcoholic media (water / methanol = 1 / 4) at ambient temperature. Then, GMA was polymerized from poly(MPC)(PMPC) brush using Cu(I)Br, bpy via a mixed solvent of 7 parts methyl-ethyl-ketone (MEK) and 3 parts ethanol at ambient temperature. The PGMA brush thickness increased linearly with polymerization time. The C/O ratio of the PMPC-b-PGMA block polymer brush surfaces determined by X-ray photoelectron spectroscopy (XPS) was similar to that of the GMA molecule (C/O=7/3). And the water contact angle of PMPC brush increased after block polymerization of GMA. These results indicated that GMA could be polymerized from PMPC brushes. GMA can immobilize biomolecules such as protein, offering effective surface for biosensing.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

We develop tailor-made functional nanogels to create novel nanobiomaterials (nanogel engineering) by self-assembling of functional associating polymers as building blocks. Self-assembled nanogels containing polymerizable groups (nanogelomers) were designed as key building blocks. Hybrid hydrogels were prepared by copolymerization of the nanogelomers in the presence or absence of 2-methacryloyloxyethyl phosphorylcholine (MPC) in semi-dilute aqueous condition. CHPMA nanogelomers acted as a cross-linker and CHP-MPC hybrid hydrogels were prepared. The hydrogels spontaneously trapped proteins. By adding ß-CD solution, trapped proteins were released as native form. The hydrogels are now applied to the artificial molecular chaperone system. We can control the formation of well-defined nano-structured hydrogels by polymerization of methacryloyl group-bearing nanogels in their appropriate condition.

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Language：Japanese   Publishing type：Research paper (international conference proceedings)  

Methacryloyl-functionalized polyphosphate (PIOP) was synthesized by ring-opening polymerization of 2-i-propyl-2-oxo-1,3,2-dioxaphospholane with 2-(2-oxo-1,3,2-dioxaphosphoroyloxyethyl methacrylate) (OPEMA). The number averaged molecular weight of the PIOP and the number of OPEMA unit in one PIOP chain were 1.2 × 10 4 and 2.2, respectively. The poly [2-methacryloyloxyethyl phosphorylcholine (MPC)] cross-linked with the PIOP was prepared by radical polymerization. The porosities of the hydrogels were controlled by salt-eluting or gas-forming processes. They influenced on mechanical properties of hydrogels, but not on degradability. The enzymatic degradation of the hydrogels was determined by soaking them into alkaline phosphatatase solution. The degradation rate of the hydrogels was significantly increased in the presence of ALP. MC3T3-E1 cells were incorporated into the porous hydrogels. Their morphology and viability of cells were observed by fluorescence microscope.

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Language：English  

<p>Various features of antithrombogenic polymer alloy containing phospholipid polymers were investigated. Surface analysis of the polymer alloy membranes with X-ray photoelectron spectroscopy (XPS) revealed that the 2-methacryloyloxyethyl phosphorylcholine (MPC) unit was located at the surface of the polymer alloy membranes even when the composition of the MPC polymer was below 10wt%. Blending of the antithrombogenic MPC polymer in the conventional polymer(polymer alloy) was suggested to be a good way to obtain new polymer biomaterials for making artificial organs. It was observed that the polymer alloys does not show any adverse effect about the mechanical and thermal properties compared with the original conventional polymers.</p>

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DOI： 10.1246/bcsj.77.2283

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DOI： 10.1021/bm049961m

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DOI： 10.1016/j.biomaterials.2003.12.047

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DOI： 10.1016/S0142-9612(03)00624-0

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DOI： 10.1002/jbm.a..20106

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DOI： 10.1002/jbm.a.10459

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

The human lymphocytes were interacted with polymer surfaces whose surface potential was controlled by the formation of a polyion complex (PIC) having a phosphorylcholine moiety. 3-(Methacryloyloxypropyl)-trimethyl ammonium iodide as the cationic unit or potassium 3-methacryloyloxypropyl sulfonate as the anionic unit was copolymerized with 2-methacryloyloxyethyl phosphorylcholine (MPC) and n-butyl methacrylate. PIC was made at the solid-liquid interface, that is, an aqueous solution containing an anionic polymer with different concentrations was contacted with a cationic polymer coated polymer membrane. The formation process of PIC was followed using a quartz crystal microbalance, and the PIC surfaces were analyzed by zeta-potential and X-ray photoelectron spectroscopy. The surface potential on the PIC was controllable from +20 to -16 mV, which increased in the amount of adsorbed anionic copolymer as the zeta-potential decreased toward the negative charge. The PIC surface in contact with human lymphocyte for 5 h was observed using a scanning electron microscopy and the density of the adherent human lymphocyte was determined by the lactate dehydrogenase method. The lymphocyte adhesion on the surface was gradually reduced with an increase in the negative value of the zeta-potential. The morphological change in the adherent lymphocytes was not observed on the polymer surfaces with MPC units. The adherent lymphocytes were not activated on the PIC surface. The lymphocyte adhesion with reduced activation could be controlled by changing the surface potential on the polymer with the MPC unit. (C) 2003 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S1468-6996(03)00014-7

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DOI： 10.1016/S0142-9612(03)00450-2

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DOI： 10.1002/mabi.200390031

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DOI： 10.1002/jbm.a.10572

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DOI： 10.1016/S0142-9612(02)00135-7

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DOI： 10.1046/j.1525-1594.2002.07039.x

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DOI： 10.1067/mpr.2002.129383

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DOI： 10.1016/S0142-9612(02)00246-6

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DOI： 10.1016/S0927-7765(02)00006-1

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DOI： 10.1002/jbm.10339

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DOI： 10.1002/jbm.10210

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Society of Polymer Science  

To improve the blood compatibility of the surface of stainless steel, which is used as a base material of stent for cardiovascular treatment, the surface was coated with a 2-methacryloyloxyethyl phosphorylcholine (MPC) polymer. 4-Methacryloyloxyethyl trimellitate anhydride (4-META)/methyl methacrylate (MMA) polymer was precoated on the stainless steel plate as a binder to obtain the long term stability of the MPC polymer. The surface of modified stainless steel was analyzed with XPS. The amount of the polymer eluted from the surfaces was evaluated by soaking samples in water for 14 days at 37°C. All of MPC polymer directly coated on stainless plate was eluted after 14 days soaking. On the other hand, the elution of the MPC polymer was significantly reduced by precoating of 4-META/MMA polymer on stainless plate. This surface effectively reduced protein adsorption and platelet adhesion. MPC polymer coated with 4-META/MMA polymer on stainless steel will be a useful technique as surface modification of the stent.

DOI： 10.1295/koron.59.432

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DOI： 10.1016/S0142-9612(00)00373-2

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DOI： 10.1016/S0142-9612(00)00180-0

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DOI： 10.1002/1097-4636(200110)57:1<72::AID-JBM1143>3.0.CO;2-G

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DOI： 10.1002/(SICI)1521-3927(20000301)21:6<287::AID-MARC287>3.0.CO;2-W

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DOI： 10.1002/1097-4636(20001215)52:4<701::AID-JBM15>3.0.CO;2-6

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DOI： 10.1016/S0927-7765(99)00158-7

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Language：Japanese   Publisher：JAPANESE SOCIETY FOR ARTIFICIAL ORGANS  

DOI： 10.11392/jsao1972.28.670

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DOI： 10.1163/156856299X00676

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Publishing type：Research paper (scientific journal)  

DOI： 10.1002/(SICI)1097-4636(199802)39:2<323::AID-JBM21>3.0.CO;2-C

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Publishing type：Research paper (scientific journal)  

DOI： 10.1016/S0928-4931(98)00059-9

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Publishing type：Research paper (scientific journal)  

DOI： 10.1177/088532829801300203

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Publishing type：Research paper (scientific journal)  

DOI： 10.1163/156856298X00163

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Publishing type：Research paper (scientific journal)  

DOI： 10.1002/(SICI)1097-4636(19970915)36:4<508::AID-JBM8>3.0.CO;2-I

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Publishing type：Research paper (scientific journal)  

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Publishing type：Research paper (scientific journal)  

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Language：English  

<p>Research was conducted to determine if semi-interpenetrating polymer network (sIPN) surface formation, using a crosslinked MPC copolymer, is an effective method to produce a stable surface treatment. The materials' ability to suppress fibroblast attachment was also investigated. Four materials were fabricated and tested: solution cast Tecoflex SG93A; a solution cast blend of Tecoflex and 7.5 wt.% Mpc(30 mol%)-co-cyclohexyl methacrylate (CHMA); a solution cast blend of Tecoflex and 7.5 wt.% MPC(30 mol%)-co-2-ethylexyl methacrylate (EHMA); and a sequential surface sPIN. Examination by scanning electron microscopy (SEM) revealed that sIPN produced the best results with no cell attachment visible on the material surface.</p>

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Language：English  

<p>Phospholipid polymers with various poly(oxyethylene) were synthesized and their phospholipid adsorption, protein adsorption, and platelet adhesion were studied. The polymer containing 30mol% phospholipid moiety suppressed platelet adhesion. On the methacryloyloxyalkyl phosphorylcholines (MAPC) copolymer with 10mol% MAPC composition, the number of platelet decreased with an increase in the length of methylene chain because of the increase of affinity to phospholipid while on MEOnPC copolymer, the number of platelet increased with the increased in oxyethylene chain length. The MAPC polymers with 2 to 6 methylene chain length have good blood compatible materials.</p>

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Publishing type：Research paper (scientific journal)  

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Publishing type：Research paper (scientific journal)  

DOI： 10.1163/156856296X00228

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Publishing type：Research paper (scientific journal)  

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Publishing type：Research paper (scientific journal)  

DOI： 10.1002/(SICI)1097-4636(199611)32:3<401::AID-JBM13>3.0.CO;2-J

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