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Delivery of Oridonin and Methotrexate via PEGylated Graphene Oxide

  • Dongdong Chai
    Dongdong Chai
    Department of Anesthesiology, Shanghai Ninth People’s Hospital, Shanghai Jiao Tong University, School of Medicine, Center for Specialty Strategy Research of Shanghai Jiao Tong University China Hospital Development Institute, 639 Zhizaoju Road, Shanghai 200011, People’s Republic of China
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  • , 
  • Bingjie Hao
    Bingjie Hao
    Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People’s Republic of China
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  • , 
  • Rong Hu
    Rong Hu
    Department of Anesthesiology, Shanghai Ninth People’s Hospital, Shanghai Jiao Tong University, School of Medicine, Center for Specialty Strategy Research of Shanghai Jiao Tong University China Hospital Development Institute, 639 Zhizaoju Road, Shanghai 200011, People’s Republic of China
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  • , 
  • Fang Zhang*
    Fang Zhang
    The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, People’s Republic of China
    *E-mail: [email protected]. Tel: +86-21-64321673. Fax: +86-21-64322272 (F.Z.).
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    Orcidhttp://orcid.org/0000-0002-9656-8893
  • , 
  • Jia Yan
    Jia Yan
    Department of Anesthesiology, Shanghai Ninth People’s Hospital, Shanghai Jiao Tong University, School of Medicine, Center for Specialty Strategy Research of Shanghai Jiao Tong University China Hospital Development Institute, 639 Zhizaoju Road, Shanghai 200011, People’s Republic of China
    More by Jia Yan
  • , 
  • Yu Sun
    Yu Sun
    Department of Anesthesiology, Shanghai Ninth People’s Hospital, Shanghai Jiao Tong University, School of Medicine, Center for Specialty Strategy Research of Shanghai Jiao Tong University China Hospital Development Institute, 639 Zhizaoju Road, Shanghai 200011, People’s Republic of China
    More by Yu Sun
  • , 
  • Xiaoyu Huang*
    Xiaoyu Huang
    Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People’s Republic of China
    *E-mail: [email protected]. Tel: +86-21-54925310. Fax: +86-21-64166128 (X.H.).
    More by Xiaoyu Huang
    Orcidhttp://orcid.org/0000-0002-9781-972X
  • , 
  • Qingxiao Zhang
    Qingxiao Zhang
    The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, People’s Republic of China
    More by Qingxiao Zhang
  • , and 
  • Hong Jiang*
    Hong Jiang
    Department of Anesthesiology, Shanghai Ninth People’s Hospital, Shanghai Jiao Tong University, School of Medicine, Center for Specialty Strategy Research of Shanghai Jiao Tong University China Hospital Development Institute, 639 Zhizaoju Road, Shanghai 200011, People’s Republic of China
    *E-mail: [email protected]. Tel: +86-21-23271699. Fax: +86-21-63136856 (H.J.).
    More by Hong Jiang
Cite this: ACS Appl. Mater. Interfaces 2019, 11, 26, 22915–22924
Publication Date (Web):June 5, 2019
https://doi.org/10.1021/acsami.9b03983
Copyright © 2019 American Chemical Society
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    Abstract

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    Graphene oxide (GO) possessing plenty of hydroxyls and carboxyls is often used in the field of biomedicine. To improve its water solubility and biocompatibility, 6-armed poly(ethylene glycol) (PEG) was bonded on the surface of GO sheets via a facile amidation process to form the universal drug delivery platform (GO-PEG10K-6arm) with a 200 nm size in favor of the enhanced permeability and retention effect. Herein, we prepared the stable and biocompatible platform of GO-PEG10K-6arm under mild conditions and characterized the chemical structure and micromorphology via thermogravimetric analysis and atomic force microscopy. This nanosized GO-PEG10K-6arm was found to be of very low toxicity to human normal cells of 293T and tumor cells of CAL27, MG63, and HepG2. Moreover, oridonin and methotrexate (MTX), widely used hydrophobic cancer chemotherapy drugs, were compounded with GO-PEG10K-6arm via π–π stacking and hydrophobic interactions so as to afford nanocomplexes of oridonin@GO-PEG10K-6arm and MTX@GO-PEG10K-6arm, respectively. Both nanocomplexes could quickly enter into tumor cells, which was evidenced by inverted fluorescence microscopy using fluorescein isothiocyanate as a probe, and they both showed remarkably high cytotoxicity to the tumor cells of CAL27, MG63, and HepG2 within a broad range of concentration in comparison with free drugs. This kind of nanoscale drug delivery system based on GO-PEG10K-6arm may have potential applications in biomedicine, and GO-PEG10K-6arm would be a universal and available carrier for extensive hydrophobic anticarcinogens.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsami.9b03983.

    • Materials; measurements; DLS of GO, GO-PEG10K-6arm, and MTX@GO-PEG10K-6arm; AFM images of GO-PEG10K-6arm and MTX@GO-PEG10K-6arm; DTG curves of GO, 6-armed PEG-NH2, and GO-PEG10K-6arm; UV/vis absorption spectra of oridonin, MTX, and MTX@GO-PEG10K-6arm; DAPI and FITC images of CAL27 cells incubated with MTX@GO-PEG10K-6arm-FITC; and relative cell viability of CAL27 cells after treatment with free MTX and MTX@GO-PEG10K-6arm (PDF)

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