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Synthesis of Highly pH-Responsive Glucose Poly(orthoester)

Authors

  • Lingyao Li,

    1. Department of Chemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48858 (USA)
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    • These authors contributed equally to the experimental work.

  • Yi Xu,

    1. Department of Chemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48858 (USA)
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    • These authors contributed equally to the experimental work.

  • Ian Milligan,

    1. Department of Chemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48858 (USA)
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  • Liye Fu,

    1. Department of Chemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48858 (USA)
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  • Emily A. Franckowiak,

    1. Department of Chemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48858 (USA)
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  • Prof. Wenjun Du

    Corresponding author
    1. Department of Chemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48858 (USA)
    • Department of Chemistry, Science of Advanced Materials, Central Michigan University, Mount Pleasant, MI 48858 (USA)

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  • The authors thank Dr. Benjamin M. Swarts for helpful discussions. The authors are grateful to Central Michigan University for financial support (C61661).

Abstract

pH-Responsive polymers have great potential in biomedical applications, including the selective delivery of preloaded drugs to tissues with low pH values. These polymers usually contain acid-labile linkages such as esters and acetals/ketals. However, these linkages are only mildly pH-responsive with relatively long half-lives (t1/2). Orthoester linkages are more acid-labile, but current methods suffer from synthetic challenges and are limited to the availability of monomers. To address these limitations, a sugar poly(orthoester) was synthesized as a highly pH-responsive polymer. The synthesis was achieved by using 2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide as a difunctional AB monomer and tetra-n-butylammonium iodide (TBAI) as an effective promoter. Under optimal conditions, polymers with molecular weights of 6.9 kDa were synthesized in a polycondensation manner. The synthesized glucose poly(orthoester), wherein all sugar units were connected through orthoester linkages, was highly pH-responsive with a half-life of 0.9, 0.6, and 0.2 hours at pH 6, 5, and 4, respectively.

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