Synthesis and biological evaluation of N-naphthoyl-phenylglyoxamide-based small molecular antimicrobial peptide mimics as novel antimicrobial agents and biofilm inhibitors
Antimicrobial peptides (AMPs) are a key component of the human immune system. Synthetic AMP mimics represent a novel strategy to counteract the increasing incidence of antimicrobial resistance. Here, we describe the synthesis of novel glyoxamide derivatives via ring-opening reactions of N-hexanoyl,...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2016-04, Vol.14 (14), p.3623-3637 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Nizalapur, Shashidhar Ho, Kitty K K Kimyon, Önder Yee, Eugene Berry, Thomas Manefield, Mike Cranfield, Charles G Willcox, Mark Black, David StC Kumar, Naresh |
| description | Antimicrobial peptides (AMPs) are a key component of the human immune system. Synthetic AMP mimics represent a novel strategy to counteract the increasing incidence of antimicrobial resistance. Here, we describe the synthesis of novel glyoxamide derivatives via ring-opening reactions of N-hexanoyl, N-benzoyl and N-naphthoylisatins with N,N-dimethylethane-1,2-diamine and N,N-dimethylpropane-1,3-diamine. These were converted to both the hydrochloric acid (HCl) or quaternary ammonium iodide (MeI) salts and their antibacterial activity against Staphylococcus aureus was investigated by their zone-of-inhibition and minimum inhibitory concentration (MIC). The HCl salt 22b exhibited the lowest MIC of 16 μg mL(-1), whereas the corresponding MeI salt 22c had a MIC of 39 μg mL(-1). We also investigated the in vitro toxicity of active compounds against the MRC-5 normal human lung fibroblasts and their activity against established biofilm in S. aureus. |
| doi_str_mv | 10.1039/c6ob00298f |
| format | Article |
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Synthetic AMP mimics represent a novel strategy to counteract the increasing incidence of antimicrobial resistance. Here, we describe the synthesis of novel glyoxamide derivatives via ring-opening reactions of N-hexanoyl, N-benzoyl and N-naphthoylisatins with N,N-dimethylethane-1,2-diamine and N,N-dimethylpropane-1,3-diamine. These were converted to both the hydrochloric acid (HCl) or quaternary ammonium iodide (MeI) salts and their antibacterial activity against Staphylococcus aureus was investigated by their zone-of-inhibition and minimum inhibitory concentration (MIC). The HCl salt 22b exhibited the lowest MIC of 16 μg mL(-1), whereas the corresponding MeI salt 22c had a MIC of 39 μg mL(-1). We also investigated the in vitro toxicity of active compounds against the MRC-5 normal human lung fibroblasts and their activity against established biofilm in S. aureus.</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Biofilms - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Mimicry</subject><subject>Peptides - pharmacology</subject><subject>Staphylococcus</subject><subject>Sulfonylurea Compounds - chemistry</subject><subject>Sulfonylurea Compounds - pharmacology</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkctu1TAQhi0EoqWw4QEqL1GlgJ04Fy_hqAWkii6AdTSOJyeufElj54g8Ey9Zl7ZnwcIaa_Tpmxn9hLzn7CNnlfw0NEExVspufEFOuWjbgtWVfHn8l-yEvInxljEu20a8JidlI7tGNNUp-ftz82nCaCIFr6kywYa9GcBSPIBdIZngaRjpj8LDPKUpbLaYJ_Sb3dst_AFnNBYKImoaHVhLXbA4rBaW7EvGmWEJymTdjHPKLHUPvTwsUh8OaP-jYI8-HVcZjXXU-Mkok8IS35JXI9iI757qGfl9dflr9624vvn6fff5uhhE2aZCiZHVotUV67BmI4haqkF2Wg0oy1brrhS1KDlybPJjCgEEr-oaVEa10tUZ-fDonZdwt2JMvTNxQGvBY1hjz9uuLkXHK5nRi0c0HxDjgmM_L8bBsvWc9Q_h9Lvm5su_cK4yfP7kXZVDfUSf06juASh0kEE</recordid><startdate>20160414</startdate><enddate>20160414</enddate><creator>Nizalapur, Shashidhar</creator><creator>Ho, Kitty K K</creator><creator>Kimyon, Önder</creator><creator>Yee, Eugene</creator><creator>Berry, Thomas</creator><creator>Manefield, Mike</creator><creator>Cranfield, Charles G</creator><creator>Willcox, Mark</creator><creator>Black, David StC</creator><creator>Kumar, Naresh</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0003-3608-5440</orcidid></search><sort><creationdate>20160414</creationdate><title>Synthesis and biological evaluation of N-naphthoyl-phenylglyoxamide-based small molecular antimicrobial peptide mimics as novel antimicrobial agents and biofilm inhibitors</title><author>Nizalapur, Shashidhar ; 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| subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Biofilms - drug effects Microbial Sensitivity Tests Molecular Mimicry Peptides - pharmacology Staphylococcus Sulfonylurea Compounds - chemistry Sulfonylurea Compounds - pharmacology |
| title | Synthesis and biological evaluation of N-naphthoyl-phenylglyoxamide-based small molecular antimicrobial peptide mimics as novel antimicrobial agents and biofilm inhibitors |
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