ArticleJournal of the American Chemical Society2014
Enterobactin-mediated delivery of β-lactam antibiotics enhances antibacterial activity against pathogenic Escherichia coli.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 72 papers.
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Who cites it
72 citing papers in PubMed.
- A Siderophore-Antibiotic Heterodimer Imaging Agent EnablesJournal of medicinal chemistry · 2026Article
- Perspective Approaches to "Trojan Horse" Strategy Development for Combating Bacterial Pathogens.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Trojan Horses: Conjugating Siderophores and Antibiotics-A New Approach to TreatingMicroorganisms · 2026Review
- Revealing Microbial Siderophores: From Genes to Applications.Microorganisms · 2026Review
- Siderophore-Pt(IV) Conjugates as Tools to Probe Cytoplasmic Cargo Delivery to Gram-Negative Bacteria.Journal of the American Chemical Society · 2026Article
- Structure-Guided Development of Mycobacterial Thymidine Monophosphate Kinase (MtbTMPK) Inhibitors: Unlocking New Frontiers in Tuberculosis Research.Current topics in medicinal chemistry · 2026Review
- On the Question of the Regio-, Stereoselectivity and the Molecular Mechanism of the (3+2) Cycloaddition Reaction Between (Molecules (Basel, Switzerland) · 2025Article
- Stringent response-mediated ferroptosis-like death resistance underliesApplied and environmental microbiology · 2025Article
- Commensal resilience: ancient ecological lessons for the modern microbiota.Infection and immunity · 2025Review
- Strategic re-engineering of antibiotics.Nature reviews bioengineering · 2025Article
- Re-evaluation of theBiochemistry · 2025Article
- Salvage Structures, Known as Iron Chelating Agents, Acquired from the Nature and Matured in the Labs.Current medicinal chemistry · 2025Review
- The Role of Bacterial Siderophores in Infection Therapy: From Anti-Infective Mechanisms to Therapeutic Advances.International journal of nanomedicine · 2025Review
- Enterobactin and salmochelin S4 inhibit the growth ofFrontiers in cellular and infection microbiology · 2025Article
- High-Throughput Discovery of Synthetic Siderophores for Trojan Horse Antibiotics.ACS infectious diseases · 2024Article
- Location, Location, Location: Establishing Design Principles for New Antibacterials from Ferric Siderophore Transport Systems.Molecules (Basel, Switzerland) · 2024Review
- Siderophores: A Case Study in Translational Chemical Biology.Biochemistry · 2024Review
- "Off-Label Use" of the Siderophore Enterobactin Enables Targeted Imaging of Cancer with Radioactive TiAngewandte Chemie (International ed. in English) · 2024Article
- Investigation of Siderophore-Platinum(IV) Conjugates Reveals Differing Antibacterial Activity and DNA Damage Depending on the Platinum Cargo.ACS infectious diseases · 2024Article
- Exploring the Antibacterial Activity and Cellular Fates of Enterobactin-Drug Conjugates That Target Gram-Negative Bacterial Pathogens.Accounts of chemical research · 2024Article
12 more citing papers are in PubMed but not listed here.
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2 authors.
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Abstract
The design, synthesis, and characterization of enterobactin-antibiotic conjugates, hereafter Ent-Amp/Amx, where the β-lactam antibiotics ampicillin (Amp) and amoxicillin (Amx) are linked to a monofunctionalized enterobactin scaffold via a stable poly(ethylene glycol) linker are reported. Under conditions of iron limitation, these siderophore-modified antibiotics provide enhanced antibacterial activity against Escherichia coli strains, including uropathogenic E. coli CFT073 and UTI89, enterohemorrhagic E. coli O157:H7, and enterotoxigenic E. coli O78:H11, compared to the parent β-lactams. Studies with E. coli K-12 derivatives defective in ferric enterobactin transport reveal that the enhanced antibacterial activity observed for this strain requires the outer membrane ferric enterobactin transporter FepA. A remarkable 1000-fold decrease in minimum inhibitory concentration (MIC) value is observed for uropathogenic E. coli CFT073 relative to Amp/Amx, and time-kill kinetic studies demonstrate that Ent-Amp/Amx kill this strain more rapidly at 10-fold lower concentrations than the parent antibiotics. Moreover, Ent-Amp and Ent-Amx selectively kill E. coli CFT073 co-cultured with other bacterial species such as Staphylococcus aureus, and Ent-Amp exhibits low cytotoxicity against human T84 intestinal cells in both the apo and iron-bound forms. These studies demonstrate that the native enterobactin platform provides a means to effectively deliver antibacterial cargo across the outer membrane permeability barrier of Gram-negative pathogens utilizing enterobactin for iron acquisition.
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