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Shape Memory Behavior of Biocompatible Polyurethane Stereoelastomers Synthesized via Thiol–Yne Michael Addition

  • Yen-Hao Hsu
    Yen-Hao Hsu
    Department of Chemistry, Duke University, Durham, North Carolina 27708, United States
    More by Yen-Hao Hsu
  • Derek Luong
    Derek Luong
    Department of Chemistry, Duke University, Durham, North Carolina 27708, United States
    More by Derek Luong
  • Darya Asheghali
    Darya Asheghali
    Department of Chemistry, Duke University, Durham, North Carolina 27708, United States
  • Andrew P. Dove*
    Andrew P. Dove
    School of Chemistry, University of Birmingham, Birmingham B15 2TT, U.K.
    *Email: [email protected]
  • , and 
  • Matthew L. Becker*
    Matthew L. Becker
    Department of Chemistry, Duke University, Durham, North Carolina 27708, United States
    Departments of Mechanical Engineering and Materials Science, Biomedical Engineering, Orthopaedic Surgery Duke University, Durham, North Carolina 27708, United States
    *Email: [email protected]
Cite this: Biomacromolecules 2022, 23, 3, 1205–1213
Publication Date (Web):January 19, 2022
https://doi.org/10.1021/acs.biomac.1c01473
Copyright © 2022 American Chemical Society

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    Abstract

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    Biodegradable shape memory elastomers have the potential for use in soft tissue engineering, drug delivery, and device fabrication applications. Unfortunately, few materials are able to meet the targeted degradation and mechanical properties needed for long-term implantable devices. In order to overcome these limitations, we have designed and synthesized a series of unsaturated polyurethanes that are elastic, degradable, and nontoxic to cells in vitro. The polymerization included a nucleophilic thiol–yne Michael addition between a urethane-based dipropiolate and a dithiol to yield an α,β-unsaturated carbonyl moiety along the polymer backbone. The alkene stereochemistry of the materials was tuned between 32 and 82% cis content using a combination of an organic base and solvent polarity, which collectively direct the nucleophilic addition. The bulk properties such as tensile strength, modulus, and glass transition temperature can also be tuned broadly, and the hydrogen bonding imparted by the urethane moiety allows for these materials to elicit cyclic shape memory behavior. We also demonstrated that the in vitro degradation properties are highly dependent on the alkene stereochemistry.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.biomac.1c01473.

    • Synthetic schemes and details, 1H NMR and 13C NMR spectra, polymer characterization, mechanical property measurements, and cell viability measurements (PDF)

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    Cited By

    This article is cited by 7 publications.

    1. Matthew Oshinowo, Marco Piccini, Gabriele Kociok-Köhn, Frank Marken, Antoine Buchard. Xylose- and Nucleoside-Based Polymers via Thiol–ene Polymerization toward Sugar-Derived Solid Polymer Electrolytes. ACS Applied Polymer Materials 2024, 6 (3) , 1622-1632. https://doi.org/10.1021/acsapm.3c02119
    2. Arunava Maity, Jiayi Chen, Noémie Wilson-Faubert, Audrey Laventure, Ali Nazemi. Harnessing Activated Alkyne-Hydroxyl “Click” Chemistry for Degradable and Self-Healing Poly(urea vinyl ether ester)s. Macromolecules 2024, 57 (1) , 305-316. https://doi.org/10.1021/acs.macromol.3c01574
    3. Shaoyun He, Shikai Hu, Yaowen Wu, Ruiheng Jin, Zhihao Niu, Runguo Wang, Jiajia Xue, Sizhu Wu, Xiuying Zhao, Liqun Zhang. Polyurethanes Based on Polylactic Acid for 3D Printing and Shape-Memory Applications. Biomacromolecules 2022, 23 (10) , 4192-4202. https://doi.org/10.1021/acs.biomac.2c00662
    4. Joshua C. Worch, Andrew P. Dove. Click Step-Growth Polymerization and E/Z Stereochemistry Using Nucleophilic Thiol–yne/–ene Reactions: Applying Old Concepts for Practical Sustainable (Bio)Materials. Accounts of Chemical Research 2022, 55 (17) , 2355-2369. https://doi.org/10.1021/acs.accounts.2c00293
    5. Shantanu P. Nikam, Yen-Hao Hsu, Jessica R. Marks, Catalin Mateas, Natasha C. Brigham, Samantha M. McDonald, Dana S. Guggenheim, David Ruppert, Jeffrey I. Everitt, Howard Levinson, Matthew L. Becker. Anti-adhesive bioresorbable elastomer-coated composite hernia mesh that reduce intraperitoneal adhesions. Biomaterials 2023, 292 , 121940. https://doi.org/10.1016/j.biomaterials.2022.121940
    6. Antonio Veloso-Fernández, José Manuel Laza, Leire Ruiz-Rubio, Ane Martín, Melanie Taguado, Asier Benito-Vicente, Cesar Martín, José Luis Vilas. Towards a new generation of non-cytotoxic shape memory thermoplastic polyurethanes for biomedical applications. Materials Today Communications 2022, 33 , 104730. https://doi.org/10.1016/j.mtcomm.2022.104730
    7. Peerawat Prathumrat, Mostafa Nikzad, Elnaz Hajizadeh, Reza Arablouei, Igor Sbarski. Shape memory elastomers: A review of synthesis, design, advanced manufacturing, and emerging applications. Polymers for Advanced Technologies 2022, 33 (6) , 1782-1808. https://doi.org/10.1002/pat.5652

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