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Controlling the Hydration Structure with a Small Amount of Fluorine To Produce Blood Compatible Fluorinated Poly(2-methoxyethyl acrylate)

  • Ryohei Koguchi
    Ryohei Koguchi
    Soft Materials Chemistry, Institute for Materials Chemistry and Engineering, Kyushu University, Build. CE41, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
    AGC Incorporation New Product R&D Center, 1150 Hazawa-cho, Kanagawa-ku, Yokohama, Kanagawa 221-8755, Japan
  • Katja Jankova
    Katja Jankova
    Soft Materials Chemistry, Institute for Materials Chemistry and Engineering, Kyushu University, Build. CE41, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
    Department of Energy Conversion and Storage, Technical University of Denmark, Elektrovej, Build. 375, 2800 Kongens Lyngby, Denmark
  • Noriko Tanabe
    Noriko Tanabe
    AGC Incorporation Innovative Technology Research Center, 1150 Hazawa-cho, Kanagawa-ku, Yokohama, Kanagawa 221-8755, Japan
  • Yosuke Amino
    Yosuke Amino
    AGC Incorporation Innovative Technology Research Center, 1150 Hazawa-cho, Kanagawa-ku, Yokohama, Kanagawa 221-8755, Japan
    More by Yosuke Amino
  • Yuki Hayasaka
    Yuki Hayasaka
    AGC Incorporation Innovative Technology Research Center, 1150 Hazawa-cho, Kanagawa-ku, Yokohama, Kanagawa 221-8755, Japan
  • Daisuke Kobayashi
    Daisuke Kobayashi
    AGC Incorporation Innovative Technology Research Center, 1150 Hazawa-cho, Kanagawa-ku, Yokohama, Kanagawa 221-8755, Japan
  • Tatsuya Miyajima
    Tatsuya Miyajima
    AGC Incorporation Innovative Technology Research Center, 1150 Hazawa-cho, Kanagawa-ku, Yokohama, Kanagawa 221-8755, Japan
  • Kyoko Yamamoto
    Kyoko Yamamoto
    AGC Incorporation New Product R&D Center, 1150 Hazawa-cho, Kanagawa-ku, Yokohama, Kanagawa 221-8755, Japan
  • , and 
  • Masaru Tanaka*
    Masaru Tanaka
    Soft Materials Chemistry, Institute for Materials Chemistry and Engineering, Kyushu University, Build. CE41, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan
    *E-mail: [email protected]
Cite this: Biomacromolecules 2019, 20, 6, 2265–2275
Publication Date (Web):May 1, 2019
https://doi.org/10.1021/acs.biomac.9b00201
Copyright © 2019 American Chemical Society

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    Abstract

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    Poly(2-methoxyethyl acrylate) (PMEA) shows excellent blood compatibility because of the existence of intermediate water. Various modifications of PMEA by changing its main or side chain’s chemical structure allowed tuning of the water content and the blood compatibility of numerous novel polymers. Here, we exploit a possibility of manipulating the surface hydration structure of PMEA by incorporation of small amounts of hydrophobic fluorine groups in MEA polymers using atom-transfer radical polymerization and the (macro) initiator concept. Two kinds of fluorinated MEA polymers with similar molecular weights and the same 5.5 mol % of fluorine content were synthesized using the bromoester of 2,2,3,3,4,4,5,5,6,6,7,7,8,8-pentadecafluoro-1-octanol (F15) and poly(2,2,2-trifluoroethyl methacrylate) (PTFEMA) as (macro) initiators, appearing liquid and solid at room temperature, respectively. The fibrinogen adsorption of the two varieties of fluorinated MEA polymers was different, which could not be explained only by the bulk hydration structure. Both polymers show a nanostructured morphology in the hydrated state with different sizes of the features. The measured elastic modulus of the domains appearing in atomic force microscopy and the intermediate water content shed light on the distinct mechanism of blood compatibility. Contact angle measurements reveal the surface hydration dynamics—while in the hydrated state, F15-b-PMEA reorients easily to the surface exposing its PMEA part to the water, the small solid PTFEMA block with high glass-transition temperature suppresses the movement of PTFEMA-b-PMEA and its reconstruction on the surface. These findings illustrate that in order to make a better blood compatible polymer, the chains containing sufficient intermediate water need to be mobile and efficiently oriented to the water surface.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.biomac.9b00201.

    • Experimental details, detailed characterization data, DSC profiles, SEM and additional AFM images, and XPS and NMR spectra for the discussed polymers (PDF)

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    Cited By

    This article is cited by 19 publications.

    1. Shichen Liu, Shingo Kobayashi, Toshiki Sonoda, Masaru Tanaka. Poly(tertiary amide acrylate) Copolymers Inspired by Poly(2-oxazoline)s: Their Blood Compatibility and Hydration States. Biomacromolecules 2021, 22 (6) , 2718-2728. https://doi.org/10.1021/acs.biomac.1c00411
    2. An-Tsung Kuo, Shingo Urata, Ryohei Koguchi, Toshiki Sonoda, Shingo Kobayashi, Masaru Tanaka. Effects of Side-Chain Spacing and Length on Hydration States of Poly(2-methoxyethyl acrylate) Analogues: A Molecular Dynamics Study. ACS Biomaterials Science & Engineering 2021, 7 (6) , 2383-2391. https://doi.org/10.1021/acsbiomaterials.1c00388
    3. An-Tsung Kuo, Shingo Urata, Ryohei Koguchi, Toshiki Sonoda, Shingo Kobayashi, Masaru Tanaka. Molecular Dynamics Study on the Water Mobility and Side-Chain Flexibility of Hydrated Poly(ω-methoxyalkyl acrylate)s. ACS Biomaterials Science & Engineering 2020, 6 (12) , 6690-6700. https://doi.org/10.1021/acsbiomaterials.0c01220
    4. An-Tsung Kuo, Toshiki Sonoda, Shingo Urata, Ryohei Koguchi, Shingo Kobayashi, Masaru Tanaka. Elucidating the Feature of Intermediate Water in Hydrated Poly(ω-methoxyalkyl acrylate)s by Molecular Dynamics Simulation and Differential Scanning Calorimetry Measurement. ACS Biomaterials Science & Engineering 2020, 6 (7) , 3915-3924. https://doi.org/10.1021/acsbiomaterials.0c00746
    5. Ryohei Koguchi, Katja Jankova, Yuki Hayasaka, Daisuke Kobayashi, Yosuke Amino, Tatsuya Miyajima, Shingo Kobayashi, Daiki Murakami, Kyoko Yamamoto, Masaru Tanaka. Understanding the Effect of Hydration on the Bio-inert Properties of 2-Hydroxyethyl Methacrylate Copolymers with Small Amounts of Amino- or/and Fluorine-Containing Monomers. ACS Biomaterials Science & Engineering 2020, 6 (5) , 2855-2866. https://doi.org/10.1021/acsbiomaterials.0c00230
    6. Katja Jankova, Irakli Javakhishvili, Shingo Kobayashi, Ryohei Koguchi, Daiki Murakami, Toshiki Sonoda, Masaru Tanaka. Hydration States and Blood Compatibility of Hydrogen-Bonded Supramolecular Poly(2-methoxyethyl acrylate). ACS Applied Bio Materials 2019, 2 (10) , 4154-4161. https://doi.org/10.1021/acsabm.9b00363
    7. Ryohei Koguchi, Katja Jankova, Yukiko Tanaka, Aki Yamamoto, Daiki Murakami, Qizhi Yang, Bruno Ameduri, Masaru Tanaka. Altering the bio-inert properties of surfaces by fluorinated copolymers of mPEGMA. Biomaterials Advances 2023, 153 , 213573. https://doi.org/10.1016/j.bioadv.2023.213573
    8. Shingo Kobayashi, Masaru Tanaka. Design of biomaterials through direct ring-opening metathesis polymerisation of functionalised cyclic alkenes. Molecular Systems Design & Engineering 2023, 8 (8) , 960-991. https://doi.org/10.1039/D3ME00063J
    9. Junsu Park, Tomoya Ueda, Yusaku Kawai, Kumiko Araki, Makiko Kido, Bunsho Kure, Naomi Takenaka, Yoshinori Takashima, Masaru Tanaka. Simultaneous control of the mechanical properties and adhesion of human umbilical vein endothelial cells to suppress platelet adhesion on a supramolecular substrate. RSC Advances 2022, 12 (43) , 27912-27917. https://doi.org/10.1039/D2RA04885J
    10. Jie Jin, Rajani Bhat, Utkarsh Mangal, Ji-Young Seo, YouJin Min, Jaehun Yu, Dae-Eun Kim, Kenichi Kuroda, Jae-Sung Kwon, Sung-Hwan Choi. Molecular weight tuning optimizes poly(2-methoxyethyl acrylate) dispersion to enhance the aging resistance and anti-fouling behavior of denture base resin. Biomaterials Science 2022, 10 (9) , 2224-2236. https://doi.org/10.1039/D2BM00053A
    11. Ryohei Koguchi, Katja Jankova, Masaru Tanaka. Fluorine-containing bio-inert polymers: Roles of intermediate water. Acta Biomaterialia 2022, 138 , 34-56. https://doi.org/10.1016/j.actbio.2021.10.027
    12. Tiwa Yimyai, Raweewan Thiramanas, Treethip Phakkeeree, Supitchaya Iamsaard, Daniel Crespy. Adaptive Coatings with Anticorrosion and Antibiofouling Properties. Advanced Functional Materials 2021, 31 (37) https://doi.org/10.1002/adfm.202102568
    13. Mostafa Mabrouk, Hanan H. Beherei, Yukiko Tanaka, Masaru Tanaka. Investigating the Intermediate Water Feature of Hydrated Titanium Containing Bioactive Glass. International Journal of Molecular Sciences 2021, 22 (15) , 8038. https://doi.org/10.3390/ijms22158038
    14. Jia Lv, Yiyun Cheng. Fluoropolymers in biomedical applications: state-of-the-art and future perspectives. Chemical Society Reviews 2021, 50 (9) , 5435-5467. https://doi.org/10.1039/D0CS00258E
    15. Kengo Manabe, Hidefumi Nara. Construction of stable biological albumin/heparin multilayers for elastic coatings on hydrophobic antithrombogenic artificial blood vessels. Tribology International 2021, 156 , 106843. https://doi.org/10.1016/j.triboint.2020.106843
    16. Shunsuke Tazawa, Tomoki Maeda, Atsushi Hotta. Mechanical, thermal, and microstructural analyses of thermoplastic poly(2-methoxyethyl acrylate)-based polyurethane by RAFT and polyaddition. Materials Advances 2021, 2 (5) , 1657-1664. https://doi.org/10.1039/D0MA00816H
    17. Masaru Tanaka, Shigeaki Morita, Tomohiro Hayashi. Role of interfacial water in determining the interactions of proteins and cells with hydrated materials. Colloids and Surfaces B: Biointerfaces 2021, 198 , 111449. https://doi.org/10.1016/j.colsurfb.2020.111449
    18. Thomas A Horbett. Selected aspects of the state of the art in biomaterials for cardiovascular applications. Colloids and Surfaces B: Biointerfaces 2020, 191 , 110986. https://doi.org/10.1016/j.colsurfb.2020.110986
    19. Masaru Tanaka, Shingo Kobayashi, Daiki Murakami, Fumihiro Aratsu, Aki Kashiwazaki, Takashi Hoshiba, Kazuki Fukushima. Design of Polymeric Biomaterials: The “Intermediate Water Concept”. Bulletin of the Chemical Society of Japan 2019, 92 (12) , 2043-2057. https://doi.org/10.1246/bcsj.20190274

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