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A Library Approach to Cationic Amphiphilic Polyproline Helices that Target Intracellular Pathogenic Bacteria

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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Infect. Dis. 2018, 4, 9, 1300-1305
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    A Library Approach to Cationic Amphiphilic Polyproline Helices that Target Intracellular Pathogenic Bacteria
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    • Manish Nepal
      Manish Nepal
      Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2027, United States
      More by Manish Nepal
    • Mohamed F. Mohamed
      Mohamed F. Mohamed
      Department of Comparative Pathobiology, Purdue University, 625 Harrison Street, West Lafayette, Indiana 47907-2027, United States
      More by Mohamed F. Mohamed
    • Reena Blade
      Reena Blade
      Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2027, United States
      More by Reena Blade
    • Hassan E. Eldesouky
      Hassan E. Eldesouky
      Department of Comparative Pathobiology, Purdue University, 625 Harrison Street, West Lafayette, Indiana 47907-2027, United States
      More by Hassan E. Eldesouky
    • Tiffany N. Anderson
      Tiffany N. Anderson
      Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2027, United States
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    • Mohamed N. Seleem
      Mohamed N. Seleem
      Department of Comparative Pathobiology, Purdue University, 625 Harrison Street, West Lafayette, Indiana 47907-2027, United States
      More by Mohamed N. Seleem
      Orcidhttp://orcid.org/0000-0003-0939-0458
    • Jean Chmielewski*
      Jean Chmielewski
      Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2027, United States
      *E-mail: [email protected]
      More by Jean Chmielewski
      Orcidhttp://orcid.org/0000-0003-4958-7175
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    ACS Infectious Diseases

    Cite this: ACS Infect. Dis. 2018, 4, 9, 1300–1305
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    https://doi.org/10.1021/acsinfecdis.8b00124
    Published July 6, 2018
    Copyright © 2018 American Chemical Society
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    Abstract

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    A number of pathogenic bacteria reproduce inside mammalian cells and are thus inaccessible to many antimicrobial drugs. Herein, we present a facile method to a focused library of antibacterial agents known as cationic amphiphilic polyproline helices (CAPHs). We identified three CAPHs from the library with superior cell penetration within macrophages and excellent antibacterial action against both Gram-positive and Gram-negative bacteria. These cell-penetrating antibacterial CAPHs have specific subcellular localizations that allow for targeting of pathogenic bacteria at their intracellular niches, a unique feature that promotes the successful clearance of intracellular pathogens (Salmonella, Shigella, and Listeria) residing within macrophages. Furthermore, the selected CAPHs also significantly reduced bacterial infections in an in vivo model of Caenorhabditis elegans, with minimal in vivo toxicity.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsinfecdis.8b00124.

    • Synthetic procedures and compound characterization; cell localization, hemolysis, and β-galactosidase data (PDF)

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    This article is cited by 11 publications.

    1. Andrew Encinas, Reena Blade, Nader S. Abutaleb, Ahmed A. Abouelkhair, Colin Caine, Mohamed N. Seleem, Jean Chmielewski. Effects of Rigidity and Configuration of Charged Moieties within Cationic Amphiphilic Polyproline Helices on Cell Penetration and Antibiotic Activity. ACS Infectious Diseases 2024, 10 (8) , 3052-3058. https://doi.org/10.1021/acsinfecdis.4c00400
    2. Brianna E. Dalesandro, Marcos M. Pires. Induction of Endogenous Antibody Recruitment to the Surface of the Pathogen Enterococcus faecium. ACS Infectious Diseases 2021, 7 (5) , 1116-1125. https://doi.org/10.1021/acsinfecdis.0c00547
    3. Thomas A. Dietsche, Hassan E. Eldesouky, Samantha M. Zeiders, Mohamed N. Seleem, Jean Chmielewski. Targeting Intracellular Pathogenic Bacteria Through N-Terminal Modification of Cationic Amphiphilic Polyproline Helices. The Journal of Organic Chemistry 2020, 85 (11) , 7468-7475. https://doi.org/10.1021/acs.joc.0c00871
    4. Soyoung Kim, Ho Yeon Nam, Jiyoun Lee, Jiwon Seo. Mitochondrion-Targeting Peptides and Peptidomimetics: Recent Progress and Design Principles. Biochemistry 2020, 59 (3) , 270-284. https://doi.org/10.1021/acs.biochem.9b00857
    5. X. Ma, Z. Chen, M. Long. Mechanisms of Action, Biological Characteristics, and Future Prospects: A Review of Antimicrobial Peptides (A Review). Applied Biochemistry and Microbiology 2024, 60 (6) , 1044-1060. https://doi.org/10.1134/S0003683823603104
    6. Shirin Dashtbin, Shabnam Razavi, Mokhtar Ganjali Koli, Farnoosh Barneh, Sarvenaz Ekhtiari-Sadegh, Reza Akbari, Gholamreza Irajian, Kamran Pooshang Bagheri. Intracellular bactericidal activity and action mechanism of MDP1 antimicrobial peptide against VRSA and MRSA in human endothelial cells. Frontiers in Microbiology 2024, 15 https://doi.org/10.3389/fmicb.2024.1416995
    7. Gabriela Silva Cruz, Ariane Teixeira dos Santos, Erika Helena Salles de Brito, Gandhi Rádis-Baptista. Cell-Penetrating Antimicrobial Peptides with Anti-Infective Activity against Intracellular Pathogens. Antibiotics 2022, 11 (12) , 1772. https://doi.org/10.3390/antibiotics11121772
    8. Samantha M. Zeiders, Jean Chmielewski. Antibiotic–cell‐penetrating peptide conjugates targeting challenging drug‐resistant and intracellular pathogenic bacteria. Chemical Biology & Drug Design 2021, 98 (5) , 762-778. https://doi.org/10.1111/cbdd.13930
    9. Hannah E. Distaffen, Christopher W. Jones, Brittany L. Abraham, Bradley L. Nilsson. Multivalent display of chemical signals on self‐assembled peptide scaffolds. Peptide Science 2021, 113 (2) https://doi.org/10.1002/pep2.24224
    10. Vladimir Kubyshkin, Nediljko Budisa. Anticipating alien cells with alternative genetic codes: away from the alanine world!. Current Opinion in Biotechnology 2019, 60 , 242-249. https://doi.org/10.1016/j.copbio.2019.05.006
    11. Agnès Kuroki, Arnaud Kengmo Tchoupa, Matthias Hartlieb, Raoul Peltier, Katherine E.S. Locock, Meera Unnikrishnan, Sébastien Perrier. Targeting intracellular, multi-drug resistant Staphylococcus aureus with guanidinium polymers by elucidating the structure-activity relationship. Biomaterials 2019, 217 , 119249. https://doi.org/10.1016/j.biomaterials.2019.119249
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    ACS Infectious Diseases

    Cite this: ACS Infect. Dis. 2018, 4, 9, 1300–1305
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsinfecdis.8b00124
    Published July 6, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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