Well-defined drug-conjugated biodegradable nanoparticles by azide–alkyne click crosslinking in miniemulsion

Authors

  • Jiong Zou,

    1. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, New York 14260
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  • Yun Yu,

    1. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, New York 14260
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  • Lu Yu,

    1. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, New York 14260
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  • Yukun Li,

    1. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, New York 14260
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  • Chih-Kuang Chen,

    1. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, New York 14260
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  • Chong Cheng

    Corresponding author
    1. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, New York 14260
    • Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, New York 14260
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Abstract

A new type of biodegradable polymer–drug nanoconjugate was fabricated via the combination of oil-in-water miniemulsion and Huisgen azide–alkyne click chemistry. Diazide-functionalized paclitaxel (PTXL) were prepared through functional group transformation on the C-2′ and C-7 positions of PTXL and served as both drug carrier and crosslinker. Acetylene-functionalized polylactide (PLA) was used as the base polymer. Oil-in-water miniemulsion technique was used to create nanodroplets with diameters of round 50 nm, which were used as nanoreactors to control the size and morphology of the drug conjugates. Using sodium ascorbate/CuSO4·5H2O as catalysts, click reaction was performed within the nanodroplets between the azide functionalities of the PTXL-based crosslinker and the pendant acetylene groups of the functional PLA. High extent of reaction was confirmed by FTIR analysis and the resulting drug-conjugated nanoparticles were characterized by dynamic light scattering, transmission electron microscopy, and atomic force microscopy measurements. These NPs exhibited considerable degradation in proteinase K solution within 1 week. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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