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A Dual Wavelength Polymerization and Bioconjugation Strategy for High Throughput Synthesis of Multivalent Ligands

  • Zihao Li
    Zihao Li
    Centre for Advanced Macromolecular Design (CAMD) and the Australian Centre for Nanotechnology (ACN), School of Chemistry, University of New South Wales, Sydney 2052, Australia
    More by Zihao Li
  • Shashank Kosuri
    Shashank Kosuri
    Department of Biomedical Engineering, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States
  • Henry Foster
    Henry Foster
    Centre for Advanced Macromolecular Design (CAMD) and the Australian Centre for Nanotechnology (ACN), School of Chemistry, University of New South Wales, Sydney 2052, Australia
    More by Henry Foster
  • Jarrod Cohen
    Jarrod Cohen
    New Jersey Center for Biomaterials, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States
    More by Jarrod Cohen
  • Coline Jumeaux
    Coline Jumeaux
    Department of Materials, Department of Bioengineering, and the Institute for Biomedical Engineering, Imperial College London, London SW7 2AZ, United Kingdom
    Department of Medical Biochemistry and Biophysics, Karolinska Institutet, SE-17177, Stockholm, Sweden
  • Molly M. Stevens
    Molly M. Stevens
    Department of Materials, Department of Bioengineering, and the Institute for Biomedical Engineering, Imperial College London, London SW7 2AZ, United Kingdom
    Department of Medical Biochemistry and Biophysics, Karolinska Institutet, SE-17177, Stockholm, Sweden
  • Robert Chapman*
    Robert Chapman
    Centre for Advanced Macromolecular Design (CAMD) and the Australian Centre for Nanotechnology (ACN), School of Chemistry, University of New South Wales, Sydney 2052, Australia
    *[email protected]
  • , and 
  • Adam J. Gormley*
    Adam J. Gormley
    Department of Biomedical Engineering, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States
    *[email protected]
Cite this: J. Am. Chem. Soc. 2019, 141, 50, 19823–19830
Publication Date (Web):November 19, 2019
https://doi.org/10.1021/jacs.9b09899
Copyright © 2019 American Chemical Society

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    Abstract

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    Structure–function relationships for multivalent polymer scaffolds are highly complex due to the wide diversity of architectures offered by such macromolecules. Evaluation of this landscape has traditionally been accomplished case-by-case due to the experimental difficulty associated with making these complex conjugates. Here, we introduce a simple dual-wavelength, two-step polymerize and click approach for making combinatorial conjugate libraries. It proceeds by incorporation of a polymerization friendly cyclopropenone-masked dibenzocyclooctyne into the side chain of linear polymers or the α-chain end of star polymers. Polymerizations are performed under visible light using an oxygen tolerant porphyrin-catalyzed photoinduced electron/energy transfer-reversible addition–fragmentation chain-transfer (PET-RAFT) process, after which the deprotection and click reaction is triggered by UV light. Using this approach, we are able to precisely control the valency and position of ligands on a polymer scaffold in a manner conducive to high throughput synthesis.

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    • Detailed methods, cp-DIBAC characterization, and additional results (PDF)

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    Cited By

    This article is cited by 25 publications.

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