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Probing the impact of sulfur/selenium/carbon linkages on prodrug nanoassemblies for cancer therapy

Author

Listed:
  • Bingjun Sun

    (Shenyang Pharmaceutical University)

  • Cong Luo

    (Shenyang Pharmaceutical University)

  • Xuanbo Zhang

    (Shenyang Pharmaceutical University)

  • Mengran Guo

    (Shenyang Pharmaceutical University)

  • Mengchi Sun

    (Shenyang Pharmaceutical University)

  • Han Yu

    (Shenyang Pharmaceutical University)

  • Qin Chen

    (Cancer Hospital of China Medical University, Liaoning Cancer Hospital & Institute)

  • Wenqian Yang

    (Shenyang Pharmaceutical University)

  • Menglin Wang

    (Shenyang Pharmaceutical University)

  • Shiyi Zuo

    (Shenyang Pharmaceutical University)

  • Pengyu Chen

    (Shenyang Pharmaceutical University)

  • Qiming Kan

    (Shenyang Pharmaceutical University)

  • Haotian Zhang

    (Shenyang Pharmaceutical University)

  • Yongjun Wang

    (Shenyang Pharmaceutical University)

  • Zhonggui He

    (Shenyang Pharmaceutical University)

  • Jin Sun

    (Shenyang Pharmaceutical University)

Abstract

Tumor cells are characterized as redox-heterogeneous intracellular microenvironment due to the simultaneous overproduction of reactive oxygen species and glutathione. Rational design of redox-responsive drug delivery systems is a promising prospect for efficient cancer therapy. Herein, six paclitaxel-citronellol conjugates are synthesized using either thioether bond, disulfide bond, selenoether bond, diselenide bond, carbon bond or carbon-carbon bond as linkages. These prodrugs can self-assemble into uniform nanoparticles with ultrahigh drug-loading capacity. Interestingly, sulfur/selenium/carbon bonds significantly affect the efficiency of prodrug nanoassemblies. The bond angles/dihedral angles impact the self-assembly, stability and pharmacokinetics. The redox-responsivity of sulfur/selenium/carbon bonds has remarkable influence on drug release and cytotoxicity. Moreover, selenoether/diselenide bond possess unique ability to produce reactive oxygen species, which further improve the cytotoxicity of these prodrugs. Our findings give deep insight into the impact of chemical linkages on prodrug nanoassemblies and provide strategies to the rational design of redox-responsive drug delivery systems for cancer therapy.

Suggested Citation

  • Bingjun Sun & Cong Luo & Xuanbo Zhang & Mengran Guo & Mengchi Sun & Han Yu & Qin Chen & Wenqian Yang & Menglin Wang & Shiyi Zuo & Pengyu Chen & Qiming Kan & Haotian Zhang & Yongjun Wang & Zhonggui He , 2019. "Probing the impact of sulfur/selenium/carbon linkages on prodrug nanoassemblies for cancer therapy," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-11193-x
    DOI: 10.1038/s41467-019-11193-x
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    Cited by:

    1. Tian Liu & Lingxiao Li & Shuo Wang & Fudan Dong & Shiyi Zuo & Jiaxuan Song & Xin Wang & Qi Lu & Helin Wang & Haotian Zhang & Maosheng Cheng & Xiaohong Liu & Zhonggui He & Bingjun Sun & Jin Sun, 2022. "Hybrid chalcogen bonds in prodrug nanoassemblies provides dual redox-responsivity in the tumor microenvironment," Nature Communications, Nature, vol. 13(1), pages 1-15, December.
    2. Songlei Zhou & Yukun Huang & Yu Chen & Yipu Liu & Laozhi Xie & Yang You & Shiqiang Tong & Jianpei Xu & Gan Jiang & Qingxiang Song & Ni Mei & Fenfen Ma & Xiaoling Gao & Hongzhuan Chen & Jun Chen, 2023. "Reprogramming systemic and local immune function to empower immunotherapy against glioblastoma," Nature Communications, Nature, vol. 14(1), pages 1-20, December.
    3. Bowen Li & Jianwu Tian & Fu Zhang & Chongzhi Wu & Zhiyao Li & Dandan Wang & Jiahao Zhuang & Siqin Chen & Wentao Song & Yufu Tang & Yuan Ping & Bin Liu, 2024. "Self-assembled aldehyde dehydrogenase-activatable nano-prodrug for cancer stem cell-enriched tumor detection and treatment," Nature Communications, Nature, vol. 15(1), pages 1-15, December.

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