Abstract
Several N-methyl-N''-alkylguanidinium derivatives were synthesized and used as simplified analogues of niphimycin (NM), a guanidylpolyol macrolide, in structure-activity relationship studies. The C16-alkylated derivative exerted fungicidal activity by directly damaging the fungal plasma membrane and inducing oxidative stress in a manner similar to niphimycin. These results indicate that the N-methyl-N''-alkylguanidinium moiety is required for antifungal activity by NM.
MeSH terms
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / pharmacology*
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Antifungal Agents / chemistry
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Antifungal Agents / pharmacology*
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Cell Membrane / drug effects
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Cell Membrane / metabolism
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Fungi / drug effects
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Fungi / growth & development
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Gram-Positive Bacteria / drug effects
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Gram-Positive Bacteria / growth & development
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Guanidines / chemistry
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Guanidines / pharmacology
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Microbial Sensitivity Tests
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Oxidative Stress / drug effects
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Phosphatidylcholines / pharmacology
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Reactive Oxygen Species / metabolism
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Saccharomyces cerevisiae / drug effects
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Saccharomyces cerevisiae / growth & development
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Structure-Activity Relationship
Substances
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Anti-Bacterial Agents
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Antifungal Agents
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Guanidines
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Phosphatidylcholines
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Reactive Oxygen Species
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niphimycin