The DOI matches its Crossref record; 18 of the 18 references it cites were found in a registry or an index.
Enterobactin-Mediated Delivery of β-Lactam Antibiotics Enhances Antibacterial Activity against Pathogenic Escherichia coli
Open accessAbstract
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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Cites
Construction of Escherichia coli K‐12 in‐frame, single‐gene knockout mutants: the Keio collection
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Siderophore-Based Iron Acquisition and Pathogen Control
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Iron in infection and immunity
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The porin and the permeating antibiotic: a selective diffusion barrier in Gram-negative bacteria
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Cited by
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Sassone-Corsi, M., Nuccio, S.-P., Liu, H., Hernandez, D., Vu, C. T., Takahashi, A. A., Edwards, R. A., & Raffatellu, M. (2016) · Nature · doi:10.1038/nature20557 · Cited by 549
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Siderophore-based immunization strategy to inhibit growth of enteric pathogens
Sassone-Corsi, M., Chairatana, P., Zheng, T., Perez-Lopez, A., Edwards, R. A., George, M. D., Nolan, E. M., & Raffatellu, M. (2016) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1606290113 · Cited by 75
Self-citationThe battle for iron in enteric infections
Sousa Gerós, A., Simmons, A., Drakesmith, H., Aulicino, A., & Frost, J. N. (2020) · Immunology · doi:10.1111/imm.13236 · Cited by 58
Siderophores: A Case Study in Translational Chemical Biology
LeBlanc, A. R., & Wuest, W. M. (2024) · Biochemistry · doi:10.1021/acs.biochem.4c00276 · Cited by 20
Metadata
- Authors
- Zheng, T., & Nolan, E. M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-06-27
- Volume
- 136
- Issue
- 27
- Pages
- 9677-9691
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2002865102
- Cited by
- 166
- References
- 18
- FWCI
- 6.41
- Type
- journal article
- Language
- en
- Open access
- hybrid
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