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Mechanisms of Resistance

N-Arylsulfonyl Hydrazones as Inhibitors of IMP-1 Metallo-β-Lactamase

Stefan Siemann, Darryl P. Evanoff, Laura Marrone, Anthony J. Clarke, Thammaiah Viswanatha, Gary I. Dmitrienko
Stefan Siemann
1Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1
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Darryl P. Evanoff
1Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1
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Laura Marrone
1Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1
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Anthony J. Clarke
2Canadian Bacterial Diseases Network, Department of Microbiology, University of Guelph, Guelph, Ontario N1G 2W1, Canada
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Thammaiah Viswanatha
1Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1
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Gary I. Dmitrienko
1Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1
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  • For correspondence: dmitrien@muskie.uwaterloo.ca
DOI: 10.1128/AAC.46.8.2450-2457.2002
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  • FIG. 1.
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    FIG. 1.

    Structural representation of sulfonyl hydrazone derivatives (a) and cephalosporins (b). Bonds and atoms in bold depict structural similarities between the classes of compounds.

  • FIG. 2.
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    FIG. 2.

    Structural representation of compounds 14 and 15 and their IC50s.

  • FIG. 3.
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    FIG. 3.

    Dixon (A) and Cornish-Bowden (B) plots illustrating mixed-type inhibition of IMP-1-mediated nitrocefin hydrolysis by compound 6a. The inhibitor constant (Ki) was estimated by graphic analysis of the Dixon plot. Since Dixon plots are not suited for distinguishing between competitive and mixed-type inhibition kinetics, Cornish-Bowden plots were used to determine the mode of inhibition. V, initial rate (velocity) of the reaction; S, substrate concentration.

  • FIG. 4.
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    FIG. 4.

    Stereoviews depicting the active sites of the modeled complexes of sulfonyl hydrazones 1 (A) and 2c (B) with the IMP-1 metallo-β-lactamase. The models are based on the published coordinates of an enzyme-mercaptocarboxylate inhibitor complex (7). Inhibitors and selected amino acid residues lining the binding site and discussed in the text are shown in capped-stick representation (carbon, gray; nitrogen, blue; oxygen, red; sulfur, yellow). The numbers shown denote the positions of amino acid residues in the primary structure of the enzyme. The zinc ions are depicted as large magenta spheres. Water molecules, which are proposed to contribute to a network of favorable interactions between the inhibitor and the protein (see the text), are shown as small red spheres.

Tables

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  • TABLE 1.

    Influence of sulfonyl hydrazones on IMP-1-mediated nitrocefin hydrolysisa

    TABLE 1.
  • TABLE 2.

    Effect of replacement of a 2-hydroxynaphthyl group on the inhibitory activity of sulfonyl hydrazones against IMP-1

    TABLE 2.
  • TABLE 3.

    Inhibitory activity of various 2-hydroxynaphthyl, 2 methoxynaphthyl, and anthracyl derivatives on IMP-1-mediated nitrocefin hydrolysis

    TABLE 3.
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N-Arylsulfonyl Hydrazones as Inhibitors of IMP-1 Metallo-β-Lactamase
Stefan Siemann, Darryl P. Evanoff, Laura Marrone, Anthony J. Clarke, Thammaiah Viswanatha, Gary I. Dmitrienko
Antimicrobial Agents and Chemotherapy Aug 2002, 46 (8) 2450-2457; DOI: 10.1128/AAC.46.8.2450-2457.2002

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N-Arylsulfonyl Hydrazones as Inhibitors of IMP-1 Metallo-β-Lactamase
Stefan Siemann, Darryl P. Evanoff, Laura Marrone, Anthony J. Clarke, Thammaiah Viswanatha, Gary I. Dmitrienko
Antimicrobial Agents and Chemotherapy Aug 2002, 46 (8) 2450-2457; DOI: 10.1128/AAC.46.8.2450-2457.2002
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KEYWORDS

Enzyme Inhibitors
Hydrazones
Sulfonamides
beta-lactamase inhibitors

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