Design, solid-phase synthesis and evaluation of enterobactin analogs for iron delivery into the human pathogen Campylobacter jejuni
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nihms962556.pdf
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Accepted version
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Author(s)
Zamora, Cristina Y.
Madec, Amaël G. E.
Neumann, Wilma
Nolan, Elizabeth Marie
Imperiali, Barbara
Date Issued
October 2018
Journal
Bioorganic & medicinal chemistry
Publisher
Elsevier BV
Citation
Zamora, Cristina Y. et al. “Design, solid-phase synthesis and evaluation of enterobactin analogs for iron delivery into the human pathogen Campylobacter jejuni.” Bioorganic & medicinal chemistry, vol. 26, no. 19, 2018, pp. 5314-5321 © 2018 The Author(s)
Version
Author's final manuscript
Abstract
The human enteropathogen Campylobacter jejuni, like many bacteria, employs siderophores such as enterobactin for cellular uptake of ferric iron. This transport process has been shown to be essential for virulence and presents an attractive opportunity for further study of the permissiveness of this pathway to small-molecule intervention and as inspiration for the development of synthetic carriers that may effectively transport cargo into Gram-negative bacteria. In this work, we have developed a facile and robust microscale assay to measure growth recovery of C. jejuni NCTC 11168 in liquid culture as a result of ferric iron uptake. In parallel, we have established the solid-phase synthesis of catecholamide compounds modeled on enterobactin fragments. Applying these methodological developments, we show that small synthetic iron chelators of minimal dimensions provide ferric iron to C. jejuni with equal or greater efficiency than enterobactin.
MIT Department
Massachusetts Institute of Technology. Department of Biology
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-NonCommercial-NoDerivs License
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DOI of Published Version
https://doi.org/10.1016/J.BMC.2018.04.030
