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    Optimization of Acetazolamide-Based Scaffold as Potent Inhibitors of Vancomycin-Resistant Enterococcus
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    • Jatinder Kaur
      Jatinder Kaur
      Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907, United States
      More by Jatinder Kaur
      Orcidhttp://orcid.org/0000-0001-6565-7909
    • Xufeng Cao
      Xufeng Cao
      Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907, United States
      More by Xufeng Cao
    • Nader S. Abutaleb
      Nader S. Abutaleb
      Department of Comparative Pathobiology, College of Veterinary Medicine, Purdue University, 625 Harrison Street, West Lafayette, Indiana 47907, United States
      More by Nader S. Abutaleb
      Orcidhttp://orcid.org/0000-0003-1730-4150
    • Ahmed Elkashif
      Ahmed Elkashif
      Department of Comparative Pathobiology, College of Veterinary Medicine, Purdue University, 625 Harrison Street, West Lafayette, Indiana 47907, United States
      More by Ahmed Elkashif
    • Amanda L. Graboski
      Amanda L. Graboski
      Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907, United States
      More by Amanda L. Graboski
    • Aaron D. Krabill
      Aaron D. Krabill
      Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907, United States
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    • Ahmed Hassan AbdelKhalek
      Ahmed Hassan AbdelKhalek
      Department of Comparative Pathobiology, College of Veterinary Medicine, Purdue University, 625 Harrison Street, West Lafayette, Indiana 47907, United States
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      Orcidhttp://orcid.org/0000-0002-3386-4070
    • Weiwei An
      Weiwei An
      Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907, United States
      More by Weiwei An
    • Atul Bhardwaj
      Atul Bhardwaj
      Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907, United States
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    • Mohamed N. Seleem
      Mohamed N. Seleem
      Department of Comparative Pathobiology, College of Veterinary Medicine, Purdue University, 625 Harrison Street, West Lafayette, Indiana 47907, United States
      Purdue Institute for Drug Discovery, 720 Clinic Drive, West Lafayette, Indiana 47907, United States
      Purdue Institute of Inflammation, Immunology and Infectious Disease, 207 South Martin Jischke Drive, West Lafayette, Indiana 47907, United States
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      Orcidhttp://orcid.org/0000-0003-0939-0458
    • Daniel P. Flaherty*
      Daniel P. Flaherty
      Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana 47907, United States
      Purdue Institute for Drug Discovery, 720 Clinic Drive, West Lafayette, Indiana 47907, United States
      Purdue Institute of Inflammation, Immunology and Infectious Disease, 207 South Martin Jischke Drive, West Lafayette, Indiana 47907, United States
      Phone: 765-494-4761. Email: [email protected]
      More by Daniel P. Flaherty
      Orcidhttp://orcid.org/0000-0002-8305-0606
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2020, 63, 17, 9540–9562
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    https://doi.org/10.1021/acs.jmedchem.0c00734
    Published July 28, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    Vancomycin-resistant enterococci (VRE) are the second leading cause of hospital-acquired infections (HAIs) attributed to a drug-resistant bacterium in the United States, and resistance to the frontline treatments is well documented. To combat VRE, we have repurposed the FDA-approved carbonic anhydrase drug acetazolamide to design potent antienterococcal agents. Through structure–activity relationship optimization we have arrived at two leads possessing improved potency against clinical VRE strains from MIC = 2 μg/mL (acetazolamide) to MIC = 0.007 μg/mL (22) and 1 μg/mL (26). Physicochemical properties were modified to design leads that have either high oral bioavailability to treat systemic infections or low intestinal permeability to treat VRE infections in the gastrointestinal tract. Our data suggest the intracellular targets for the molecules are putative α-carbonic and γ-carbonic anhydrases, and homology modeling and molecular dynamics simulations were performed. Together, this study presents potential anti-VRE therapeutic options to provide alternatives for problematic VRE infections.

    Copyright © 2020 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jmedchem.0c00734.

    • MICs of selected analogs against vancomycin-sensitive E. faecalis strains; E. faecium ATCC 700221 reference strain in normal and CO2 conditions; tabular Caco-2 cell viability; in vitro ADMET data obtained from Eurofins Panlabs for 22 and 26; (5) tabular in vivo plasma concentrations for 22 upon oral administration (PDF)

    • NMR and MS spectra and HPLC chromatograms for each new analog synthesized (PDF)

    • α-CA homology model figures and files (.pdb format); MD simulation reports; structural files of representative MD time points (.pdb format); videos of MD simulations for AZM, 22, 26 (.mp4 format) (ZIP)

    • γ-CA homology model figures and files (.pdb format); MD simulation reports; structural files of representative MD time points (.pdb format); videos of MD simulations for AZM, 22, 26 (.mp4 format) (ZIP)

    • Molecular formula strings for compounds and some data (CSV)

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2020, 63, 17, 9540–9562
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jmedchem.0c00734
    Published July 28, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

    Article Views

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    Altmetric

    -

    Citations

    60
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.