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Open AccessFeature PaperArticle

Study of Iron Piperazine-Based Chelators as Potential Siderophore Mimetics

1
AGIR, EA 4294, UFR de Pharmacie, Université de Picardie Jules Verne, 1 rue des Louvels, 80037 Amiens, France
2
ICMR, UMR 7312, 3 Avenue du Maréchal Juin, 51100 Reims, France
3
Unité de Toxicologie Analytique, Institut de Recherche Biomédicales des Armées, 91223 Brétigny-sur-Orge, France
*
Author to whom correspondence should be addressed.
Pharmaceuticals 2019, 12(4), 160; https://doi.org/10.3390/ph12040160
Received: 20 September 2019 / Revised: 17 October 2019 / Accepted: 22 October 2019 / Published: 23 October 2019
(This article belongs to the Special Issue New Tools for Medicinal Chemists)
Gram-negative bacteria’s resistance such as Pseudomonas aeruginosa and the Burkholderia group to conventional antibiotics leads to therapeutic failure. Use of siderophores as Trojan horses to internalize antibacterial agents or toxic metals within bacteria is a promising strategy to overcome resistance phenomenon. To combat the Pseudomonas sp, we have synthesized and studied two piperazine-based siderophore mimetics carrying either catecholate moieties (1) or hydroxypyridinone groups (2) as iron chelators. These siderophore-like molecules were prepared in no more than four steps with good global yields. The physicochemical study has highlighted a strong iron affinity since their pFe values were higher than 20. 1 possesses even a pFe value superior than those of pyoverdine, the P. aeruginosa endogenous siderophore, suggesting its potential ability to compete with it. At physiological pH, 1 forms mainly a 2:3 complex with iron, whereas two species are observed for 2. Unfortunately, the corresponding Ga(III)-1 and 2 complexes showed no antibacterial activity against P. aeruginosa DSM 1117 strain. The evaluation of their siderophore-like activity showed that 1 and 2 could be internalized by the bacteria. View Full-Text
Keywords: Pseudomonas group; siderophore mimetics; chelators; iron; piperazine Pseudomonas group; siderophore mimetics; chelators; iron; piperazine
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MDPI and ACS Style

Loupias, P.; Dechamps-Olivier, I.; Dupont, L.; Vanlemmens, P.; Mullié, C.; Taudon, N.; Bouchut, A.; Dassonville-Klimpt, A.; Sonnet, P. Study of Iron Piperazine-Based Chelators as Potential Siderophore Mimetics. Pharmaceuticals 2019, 12, 160.

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