ArticleJournal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry2018
Evaluation of a reducible disulfide linker for siderophore-mediated delivery of antibiotics.
Article in Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- Perspective Approaches to "Trojan Horse" Strategy Development for Combating Bacterial Pathogens.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Self-Immolative Systems in Diagnostic and Therapeutic Applications.ChemMedChem · 2026Review
- ModularFrontiers in toxicology · 2026Article
- Headway in Synthetic Chemistry: A Gateway for Antimicrobial Trojan Horse Strategy for Drug Repurposing Against Multi-Drug ResistantIndian journal of microbiology · 2025Review
- The Role of Bacterial Siderophores in Infection Therapy: From Anti-Infective Mechanisms to Therapeutic Advances.International journal of nanomedicine · 2025Review
- Biosynthesis of a clickable pyoverdine via in vivo enzyme engineering of an adenylation domain.Microbial cell factories · 2024Article
- Exploring the Antibacterial Activity and Cellular Fates of Enterobactin-Drug Conjugates That Target Gram-Negative Bacterial Pathogens.Accounts of chemical research · 2024Article
- Siderophores as tools and treatments.npj antimicrobials and resistance · 2024Review
- A Novel Natural Siderophore Antibiotic Conjugate Reveals a Chemical Approach to Macromolecule Coupling.ACS central science · 2023Article
- Conjugates of Aminoglycosides with Stapled Peptides as a Way to Target Antibiotic-Resistant Bacteria.ACS omega · 2023Article
- Siderophore conjugates to combat antibiotic-resistant bacteria.RSC medicinal chemistry · 2023Review
- Tracking Uptake and Metabolism of Xenometallomycins Using a Multi-Isotope Tagging Strategy.ACS infectious diseases · 2022Article
- Medicinal Chemistry of Inhibitors Targeting Resistant Bacteria.Current topics in medicinal chemistry · 2022Article
- Biomimetic enterobactin analogue mediates iron-uptake and cargo transport intoChemical science · 2021Article
- Iron Acquisition Systems of Gram-negative Bacterial Pathogens Define TonB-Dependent Pathways to Novel Antibiotics.Chemical reviews · 2021Review
- Alison Butler: papers in celebration of her 2018 ACS Alfred Bader Award in Bioorganic or Bioinorganic Chemistry.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2021Article
- Biotinylation as a tool to enhance the uptake of small molecules in Gram-negative bacteria.PloS one · 2021Article
- Platform to Discover Protease-Activated Antibiotics and Application to Siderophore-Antibiotic Conjugates.Journal of the American Chemical Society · 2020Article
- Metallotherapeutics development in the age of iron-clad bacteria.Metallomics : integrated biometal science · 2020Review
- Emerging Opportunities To Manipulate Metal Trafficking for Therapeutic Benefit.Inorganic chemistry · 2019Review
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2 authors.
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Abstract
Bacterial iron uptake machinery can be hijacked for the targeted delivery of antibiotics into pathogens by attaching antibiotics to siderophores, iron chelators that are employed by bacteria to obtain this essential nutrient. We synthesized and evaluated Ent-SS-Cipro, a siderophore-antibiotic conjugate comprised of the triscatecholate siderophore enterobactin and the fluoroquinolone antibiotic ciprofloxacin that contains a self-immolative disulfide linker. This linker is designed to be cleaved after uptake into the reducing environment of the bacterial cytoplasm. We show that the disulfide bond of Ent-SS-Cipro is cleaved by reducing agents, including the cellular reductant glutathione, which results in release of the unmodified fluoroquinolone antibiotic. Antibacterial activity assays against a panel of Escherichia coli show that Ent-SS-Cipro exhibits activity against some, but not all, E. coli. This work informs the design of siderophore-antibiotic conjugates, particularly those carrying antibiotics with cytoplasmic targets that require release after uptake into bacterial cells, and indicates that disulfide linkers may not be generally applicable for conjugation strategies of antibiotics.
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