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ACS Publications. Most Trusted. Most Cited. Most Read
Vancomycin–Arginine Conjugate Inhibits Growth of Carbapenem-Resistant E. coli and Targets Cell-Wall Synthesis

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    Vancomycin–Arginine Conjugate Inhibits Growth of Carbapenem-Resistant E. coli and Targets Cell-Wall Synthesis
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    • Alexandra Antonoplis
      Alexandra Antonoplis
      Department of Chemistry, Stanford University, Stanford, California 94305, United States
      More by Alexandra Antonoplis
    • Xiaoyu Zang
      Xiaoyu Zang
      Department of Chemistry, Stanford University, Stanford, California 94305, United States
      More by Xiaoyu Zang
    • Tristan Wegner
      Tristan Wegner
      Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany
      More by Tristan Wegner
    • Paul A. Wender*
      Paul A. Wender
      Department of Chemistry, Stanford University, Stanford, California 94305, United States
      Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305, United States
      *E-mail: [email protected] (P.A.W.).
      More by Paul A. Wender
      Orcidhttp://orcid.org/0000-0001-6319-2829
    • Lynette Cegelski*
      Lynette Cegelski
      Department of Chemistry, Stanford University, Stanford, California 94305, United States
      *E-mail: [email protected] (L.C.).
      More by Lynette Cegelski
      Orcidhttp://orcid.org/0000-0002-0978-1814
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    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2019, 14, 9, 2065–2070
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    https://doi.org/10.1021/acschembio.9b00565
    Published September 3, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    The emergence of multi-drug-resistant Gram-negative bacteria, including carbapenem-resistant Enterobacteriaceae, is a major health problem that necessitates the development of new antibiotics. Vancomycin inhibits cell-wall synthesis in Gram-positive bacteria but is generally ineffective against Gram-negative bacteria and is unable to penetrate the outer membrane barrier. In an effort to determine whether vancomycin and other antibiotics effective against Gram-positive bacteria could, through modification, be rendered effective against Gram-negative bacteria, we discovered that the covalent attachment of a single arginine to vancomycin yielded conjugates with order-of-magnitude improvements in activity against Gram-negative bacteria, including pathogenic E. coli. The vancomycin–arginine conjugate (V–R) exhibited efficacy against actively growing bacteria, induced the loss of rod cellular morphology, and resulted in the intracellular accumulation of peptidoglycan precursors, all consistent with cell-wall synthesis disruption as its mechanism of action. Membrane permeabilization studies demonstrated an enhanced outer membrane permeability of V–R as compared with vancomycin. The conjugate exhibited no mammalian cell toxicity or hemolytic activity in MTT and hemolysis assays. Our study introduces a new vancomycin derivative effective against Gram-negative bacteria and underscores the broader potential of generating new antibiotics through combined mode-of-action and synthesis-informed design studies.

    Copyright © 2019 American Chemical Society

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    • Synthetic procedures and characterization data and spectra, biological procedures, and Supporting Figure 1 and Supporting Tables 1–3 (PDF)

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    Cited By

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    This article is cited by 70 publications.

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    Cite this: ACS Chem. Biol. 2019, 14, 9, 2065–2070
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    https://doi.org/10.1021/acschembio.9b00565
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