Theranostic Gallium Siderophore Ciprofloxacin Conjugate with Broad Spectrum Antibiotic Potency

Apurva Pandey, Chloé Savino, Shin Hye Ahn, Zhaoyong Yang, Steven G. Van Lanen, Eszter Boros

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

Abstract

Pathogenic bacteria scavenge ferric iron from the host for survival and proliferation using small-molecular chelators, siderophores. Here, we introduce and assess the gallium(III) complex of ciprofloxacin-functionalized desferrichrome (D2) as a potential therapeutic for bacterial infection using an in vitro assay and radiochemical, tracer-based approach. Ga-D2 exhibits a minimum inhibitory concentration of 0.23 μM in Escherichia coli, in line with the parent fluoroquinolone antibiotic. Competitive and mutant strain assays show that Ga-D2 relies on FhuA-mediated transport for internalization. Ga-D2 is potent against Pseudomonas aeruginosa (3.8 μM), Staphylococcus aureus (0.94 μM), and Klebsiella pneumoniae (12.5 μM), while Fe-D2 is inactive in these strains. Radiochemical experiments with E. coli reveal that 67Ga-D2 is taken up more efficiently than 67Ga-citrate. In naive mice, 67Ga-D2 clears renally and is excreted 13% intact in the urine. These pharmacokinetic and bacterial growth inhibitory properties qualify Ga-D2 for future investigations as a diagnosis and treatment tool for infection.

Original languageEnglish
Pages (from-to)9947-9960
Number of pages14
JournalJournal of Medicinal Chemistry
Volume62
Issue number21
DOIs
StatePublished - Nov 14 2019

Bibliographical note

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Funding

E.B. acknowledges funding sources, specifically the NIH for a Pathway to Independence Award (R00HL125728) and Stony Brook University for startup funds. S.G.V.L is supported by NIH (R01AI087849). E.B. acknowledges funding sources, specifically the NIH for a Pathway to Independence Award (R00HL125728) and Stony Brook University for startup funds. S.G.V.L is supported by NIH (R01AI087849).

FundersFunder number
E.B.
National Institutes of Health (NIH)R00HL125728
National Institute of Allergy and Infectious DiseasesR01AI087849
Stony Brook University

    ASJC Scopus subject areas

    • Molecular Medicine
    • Drug Discovery

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