ArticleChemical science2021
Total synthesis and mechanism of action of the antibiotic armeniaspirol A.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Antibiotic-producing microorganisms: taxonomic diversity, screening strategies, and emerging and underexploited antibacterial targets.Archives of microbiology · 2026Review
- Genome Mining-Driven Isolation of New Gromomycins and Insights into Their Mode of Action.ACS chemical biology · 2026Article
- Fighting Antimicrobial Resistance: Innovative Drugs in Antibacterial Research.Angewandte Chemie (International ed. in English) · 2025Review
- Antibacterial Marinopyrroles and Pseudilins Act as Protonophores.ACS chemical biology · 2024Article
- Total Synthesis and Biological Investigation of Mindapyrroles A and B.ChemMedChem · 2023Article
- Enhancing armeniaspirols production through multi-level engineering of a native Streptomyces producer.Microbial cell factories · 2023Article
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Authors and funding
19 authors.
Funding
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Abstract
Emerging antimicrobial resistance urges the discovery of antibiotics with unexplored, resistance-breaking mechanisms. Armeniaspirols represent a novel class of antibiotics with a unique spiro[4.4]non-8-ene scaffold and potent activities against Gram-positive pathogens. We report a concise total synthesis of (±) armeniaspirol A in six steps with a yield of 20.3% that includes the formation of the spirocycle through a copper-catalyzed radical cross-coupling reaction. In mechanistic biological experiments, armeniaspirol A exerted potent membrane depolarization, accounting for the pH-dependent antibiotic activity. Armeniaspirol A also disrupted the membrane potential and decreased oxygen consumption in mitochondria. In planar lipid bilayers and in unilamellar vesicles, armeniaspirol A transported protons across membranes in a protein-independent manner, demonstrating that armeniaspirol A acted as a protonophore. We provide evidence that this mechanism might account for the antibiotic activity of multiple chloropyrrole-containing natural products isolated from various origins that share a 4-acylphenol moiety coupled to chloropyrrole as a joint pharmacophore. We additionally describe an efflux-mediated mechanism of resistance against armeniaspirols.
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Registered trials
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