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Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies

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ABSTRACT

A series of novel hexadentate enterobactin analogues, which contain three catechol chelating moieties attached to different molecular scaffolds with flexible alkyl chain lengths, were prepared. The solution thermodynamic stabilities of the complexes with uranyl, ferric(III), and zinc(II) ions were then investigated. The hexadentate ligands demonstrate effective binding ability to uranyl ion, and the average uranyl affinities are two orders of magnitude higher than 2,3-dihydroxy-N1,N4-bis[(1,2-hydroxypyridinone-6-carboxamide)ethyl]terephthalamide [TMA(2Li-1,2-HOPO)2] ligand with similar denticity. The high affinity of hexadentate ligands could be due to the presence of the flexible scaffold, which favors the geometric agreement between the ligand and the uranyl coordination preference. The hexadentate ligands also exhibit higher antiradical efficiency than butylated hydroxyanisole (BHA). These results provide a basis for further studies on the potential applications of hexadentate ligands as therapeutic chelating agents.

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Species distribution curves calculated for uranyl complexes with ligand L1H6, the charge number are omitted for clarity; conditions: [UO22+] = [L1H6] = 2 × 10−5 M.
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f6: Species distribution curves calculated for uranyl complexes with ligand L1H6, the charge number are omitted for clarity; conditions: [UO22+] = [L1H6] = 2 × 10−5 M.

Mentions: The species distribution diagram of L1H6 was selected for illustration (Fig. 6) because the species distribution diagrams of the uranyl complexes with ligands L1–3H6 are similar, moreover, the diagrams of ligands L2–3H6 are shown in Figures S7 and S8.


Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
Species distribution curves calculated for uranyl complexes with ligand L1H6, the charge number are omitted for clarity; conditions: [UO22+] = [L1H6] = 2 × 10−5 M.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5037427&req=5

f6: Species distribution curves calculated for uranyl complexes with ligand L1H6, the charge number are omitted for clarity; conditions: [UO22+] = [L1H6] = 2 × 10−5 M.
Mentions: The species distribution diagram of L1H6 was selected for illustration (Fig. 6) because the species distribution diagrams of the uranyl complexes with ligands L1–3H6 are similar, moreover, the diagrams of ligands L2–3H6 are shown in Figures S7 and S8.

View Article: PubMed Central - PubMed

ABSTRACT

A series of novel hexadentate enterobactin analogues, which contain three catechol chelating moieties attached to different molecular scaffolds with flexible alkyl chain lengths, were prepared. The solution thermodynamic stabilities of the complexes with uranyl, ferric(III), and zinc(II) ions were then investigated. The hexadentate ligands demonstrate effective binding ability to uranyl ion, and the average uranyl affinities are two orders of magnitude higher than 2,3-dihydroxy-N1,N4-bis[(1,2-hydroxypyridinone-6-carboxamide)ethyl]terephthalamide [TMA(2Li-1,2-HOPO)2] ligand with similar denticity. The high affinity of hexadentate ligands could be due to the presence of the flexible scaffold, which favors the geometric agreement between the ligand and the uranyl coordination preference. The hexadentate ligands also exhibit higher antiradical efficiency than butylated hydroxyanisole (BHA). These results provide a basis for further studies on the potential applications of hexadentate ligands as therapeutic chelating agents.

No MeSH data available.


Related in: MedlinePlus