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Fluorescent Heterotelechelic Single-Chain Polymer Nanoparticles: Synthesis, Spectroscopy, and Cellular Imaging

  • Daniel N. F. Bajj
    Daniel N. F. Bajj
    Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
  • Michael V. Tran
    Michael V. Tran
    Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
  • Hsin-Yun Tsai
    Hsin-Yun Tsai
    Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
  • Hyungki Kim
    Hyungki Kim
    Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
    More by Hyungki Kim
  • Nathan R. Paisley
    Nathan R. Paisley
    Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
  • W. Russ Algar*
    W. Russ Algar
    Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
    *E-mail: [email protected]
  • , and 
  • Zachary M. Hudson*
    Zachary M. Hudson
    Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
    *E-mail: [email protected]
Cite this: ACS Appl. Nano Mater. 2019, 2, 2, 898–909
Publication Date (Web):February 5, 2019
https://doi.org/10.1021/acsanm.8b02149
Copyright © 2019 American Chemical Society

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    Abstract

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    The folding and collapse of individual polymer chains into single-chain polymer nanoparticles (SCPNs) is a versatile and emerging platform for biological applications such as diagnostics, imaging, and therapy, where components for two or more of these functions can be combined onto a single polymer carrier. Here, we prepare heterotelechelic polymers with three sets of separately addressable chemical handles at their α-terminus and ω-terminus, and along their backbone. As a model system, the α- and ω-termini are conjugated with a targeting ligand (folic acid or biotin) and therapeutic drug cargo (camptothecin), respectively, and the backbone is grafted with pendant fluorescent dye molecules, poly(ethylene glycol) oligomers, and benzene-1,3,5-tricarboxamide. These polymers fold in water to give fluorescent SCPNs, which are characterized with respect to their physical and photophysical properties. The latter reveals a relationship between polymer folding, quantum yield, and resistance to photobleaching. The SCPNs are then shown to be useful for immunolabeling of SK-BR-3 breast cancer cells and exhibit little or no acute cytotoxicity. This work demonstrates that SCPNs can be used as a viable platform for bioconjugation and cell labeling, helps establish a set of design criteria for optimizing future biological applications, and opens the door to the development of SCPNs for a broader range of theranostic applications.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsanm.8b02149.

    • Detailed experimental methods and additional results, including a full list of materials, experiment conditions, synthetic procedures, characterization methods, cell experiment protocols, 1H and 19F NMR spectra, gel permeation chromatography data, additional photophysical data, and additional cell labeling data (PDF)

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    This article is cited by 15 publications.

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    8. Chengyuan Wang, Arielle Mann, Matthew D. Hannigan, Regina H. Garvey, Bianca L. Dumlao, Marcus Weck. Folded Well‐Defined 3D Architecture from Synthetic Helical and Sheet‐Like Polymers. Advanced Functional Materials 2024, 39 https://doi.org/10.1002/adfm.202313734
    9. Linlin Deng, Alis R. Olea, Ana Ortiz‐Perez, Bingbing Sun, Jianhong Wang, Silvia Pujals, Anja R. A. Palmans, Lorenzo Albertazzi. Imaging Diffusion and Stability of Single‐Chain Polymeric Nanoparticles in a Multi‐Gel Tumor‐on‐a‐Chip Microfluidic Device. Small Methods 2024, 8 https://doi.org/10.1002/smtd.202301072
    10. Naomi M. Hamelmann, Jos M.J. Paulusse. Single-chain polymer nanoparticles in biomedical applications. Journal of Controlled Release 2023, 356 , 26-42. https://doi.org/10.1016/j.jconrel.2023.02.019
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    12. Melissa A. Reith, Sinan Kardas, Chiel Mertens, Mathieu Fossépré, Mathieu Surin, Jan Steinkoenig, Filip E. Du Prez. Using nickel to fold discrete synthetic macromolecules into single-chain nanoparticles. Polymer Chemistry 2021, 12 (34) , 4924-4933. https://doi.org/10.1039/D1PY00229E
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    14. Ester Verde-Sesto, Arantxa Arbe, Angel J. Moreno, Daniele Cangialosi, Angel Alegría, Juan Colmenero, José A. Pomposo. Single-chain nanoparticles: opportunities provided by internal and external confinement. Materials Horizons 2020, 7 (9) , 2292-2313. https://doi.org/10.1039/D0MH00846J
    15. Hendrik Frisch, Bryan T. Tuten, Christopher Barner‐Kowollik. Macromolecular Superstructures: A Future Beyond Single Chain Nanoparticles. Israel Journal of Chemistry 2020, 60 (1-2) , 86-99. https://doi.org/10.1002/ijch.201900145

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