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Download Hi-Res ImageDownload to MS-PowerPointCite This:Biomacromolecules 2019, 20, 6, 2230-2240
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Design and Synthesis of Biocompatible, Hemocompatible, and Highly Selective Antimicrobial Cationic Peptidopolysaccharides via Click Chemistry

  • Yun Chen
    Yun Chen
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Yun Chen
    • , 
  • Luofeng Yu
    Luofeng Yu
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Luofeng Yu
    • , 
  • Biao Zhang
    Biao Zhang
    Xi’an Institute of Flexible Electronics (IFE) & Xi’an Institute of Biomedical Materials and Engineering (IBME), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi’an 710072, P. R. China
    More by Biao Zhang
    • , 
  • Wei Feng
    Wei Feng
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Wei Feng
    • , 
  • Miao Xu
    Miao Xu
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Miao Xu
    • , 
  • Lingling Gao
    Lingling Gao
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Lingling Gao
    • , 
  • Nian Liu
    Nian Liu
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Nian Liu
    • , 
  • Qianqian Wang
    Qianqian Wang
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Qianqian Wang
    • , 
  • Xiao Huang
    Xiao Huang
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    More by Xiao Huang
    Orcidhttp://orcid.org/0000-0002-0106-7763
    • , 
  • Peng Li*
    Peng Li
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    Xi’an Institute of Flexible Electronics (IFE) & Xi’an Institute of Biomedical Materials and Engineering (IBME), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi’an 710072, P. R. China
    *E-mail: [email protected]
    More by Peng Li
    Orcidhttp://orcid.org/0000-0002-5876-2177
    • , and 
  • Wei Huang
    Wei Huang
    Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, P. R. China
    Xi’an Institute of Flexible Electronics (IFE) & Xi’an Institute of Biomedical Materials and Engineering (IBME), Northwestern Polytechnical University (NPU), 127 West Youyi Road, Xi’an 710072, P. R. China
    More by Wei Huang
Cite this: Biomacromolecules 2019, 20, 6, 2230–2240
Publication Date (Web):May 9, 2019
https://doi.org/10.1021/acs.biomac.9b00179
Copyright © 2019 American Chemical Society
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Abstract

Abstract Image

Despite the excellent antimicrobial activity, the high toxicity and low selectivity of cationic antimicrobial peptides (AMPs) and their synthetic analogues impede their biomedical applications. In this study, we report a series of cationic peptidopolysaccharides synthesized by thiol–ene click chemistry of grafting antimicrobial polypeptides, methacrylate-ended poly(lysine-random-phenylalanine) (Me-KnFm), onto a thiolated polysaccharide (dextran, Dex) backbone. Their copolymers (Dex-g-KnFm) exhibit potent broad-spectrum antibacterial and antifungal activity against Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), Gram-positive bacteria [methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus epidermidis], and fungi (Candida albicans) with minimal inhibitory concentrations in the range of 31.25–500 μg·mL–1. More importantly, Dex-g-KnFm copolymers did not induce drug resistance of MRSA up to 17 passages. In addition, these copolymers have an improved hemocompatibility and exhibit good in vitro biocompatibility with murine myoblast (C2C12) cells. Among the synthesized peptidopolysaccharides, DexL-g-K12.5F12.5-50%, as the optimal agent, displayed a selectivity more than 200 times the maximum value of polypeptide molecules. Furthermore, a strong in vivo antimicrobial efficacy with a log reduction above 3 in a mouse bacterial sepsis model has been obtained. These excellent biological properties present a promising prospect for Dex-g-KnFm in biomedical applications.

Supporting Information

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.biomac.9b00179.

  • Synthesis scheme of Me-KnFm; 1H NMR spectra of Lys(Z)-NCA, Phe-NCA, Me-KnFm(Z), Me-KnFm, Dex-4NC, Dex-SH, and Dex-g-KnFm; GPC of polypeptides and peptidopolysaccharides; red blood cell hemolysis after exposure to peptidopolysaccharides; MIC/MLC and hemolytic activity of some polymers; and Mn, PDI, DP, and DS of polypeptides and peptidopolysaccharides (PDF)

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Cited By

This article is cited by 8 publications.

  1. Jiangna Guo, Yuanmei Qian, Bin Sun, Zhe Sun, Zhengsheng Chen, Hailei Mao, Bin Wang, Feng Yan. Antibacterial Amino Acid-Based Poly(ionic liquid) Membranes: Effects of Chirality, Chemical Bonding Type, and Application for MRSA Skin Infections. ACS Applied Bio Materials 2019, 2 (10) , 4418-4426. https://doi.org/10.1021/acsabm.9b00619
  2. Miao Xu, Abidullah Khan, Tengjiao Wang, Qing Song, Chunmao Han, Qianqian Wang, Lingling Gao, Xiao Huang, Peng Li, Wei Huang. Mussel-Inspired Hydrogel with Potent in Vivo Contact-Active Antimicrobial and Wound Healing Promoting Activities. ACS Applied Bio Materials 2019, 2 (8) , 3329-3340. https://doi.org/10.1021/acsabm.9b00353
  3. Jiayan Zhou, Chunyang Sun, Chunshui Yu. Highly-controllable drug release from core cross-linked singlet oxygen-responsive nanoparticles for cancer therapy. RSC Advances 2020, 10 (34) , 19997-20008. https://doi.org/10.1039/D0RA02053B
  4. Lin Wang, Yuanzhao Li, Lizhun Lin, Ruojun Mu, Jie Pang. Novel synthesis of mussel inspired and Fe3+ induced pH-sensitive hydrogels: Adhesion, injectable, shapeable, temperature properties, release behavior and rheological characterization. Carbohydrate Polymers 2020, 236 , 116045. https://doi.org/10.1016/j.carbpol.2020.116045
  5. Jueqin She, Yan Li, Chao Zhou, Shuguang Chen, Jianghua Li, Yue-Fei Zhang, Feifei Zhang, Bo Liu. Unusual allyl diazoacetate/acrolein copolymer-based hydrogels as promising antimicrobial agents for effective bacteria therapy. Chemical Engineering Journal 2020, , 124114. https://doi.org/10.1016/j.cej.2020.124114
  6. Andrea Barrios-Gumiel, Javier Sanchez-Nieves, Jorge Pérez-Serrano, Rafael Gómez, F. Javier de la Mata. PEGylated AgNP covered with cationic carbosilane dendrons to enhance antibacterial and inhibition of biofilm properties. International Journal of Pharmaceutics 2019, , 118591. https://doi.org/10.1016/j.ijpharm.2019.118591
  7. Rimesh Augustine, Nagendra Kalva, Ho An Kim, Yu Zhang, Il Kim. pH-Responsive Polypeptide-Based Smart Nano-Carriers for Theranostic Applications. Molecules 2019, 24 (16) , 2961. https://doi.org/10.3390/molecules24162961
  8. Qinggele Borjihan, Jiebing Yang, Qing Song, Lingling Gao, Miao Xu, Tianyi Gao, Wenxin Liu, Peng Li, Quanshun Li, Alideertu Dong. Povidone-iodine-functionalized fluorinated copolymers with dual-functional antibacterial and antifouling activities. Biomaterials Science 2019, 7 (8) , 3334-3347. https://doi.org/10.1039/C9BM00583H

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