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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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Molecular structure of related compounds.
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f2: Molecular structure of related compounds.

Mentions: The protonation constants log KiH (i = 1, 2, 3 …) of ligands L1–3H6 were determined from spectrophotometric titration measurements in aqueous KCl solution an ionic strength of 0.10 M at 298.2 K. The protonation constants for the intermediate L7–9H2 were also measured and compared with that for ligands L1–3H6. The determined log KiH values (i = 4–6) and estimated values of the related ligands are listed in Table 1 303132 (Fig. 2 for the corresponding structures). The values of L7–9H2 are listed in Table S1.


Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
Molecular structure of related compounds.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f2: Molecular structure of related compounds.
Mentions: The protonation constants log KiH (i = 1, 2, 3 …) of ligands L1–3H6 were determined from spectrophotometric titration measurements in aqueous KCl solution an ionic strength of 0.10 M at 298.2 K. The protonation constants for the intermediate L7–9H2 were also measured and compared with that for ligands L1–3H6. The determined log KiH values (i = 4–6) and estimated values of the related ligands are listed in Table 1 303132 (Fig. 2 for the corresponding structures). The values of L7–9H2 are listed in Table S1.

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.