Symmetrical 1,3-dicarbonyl biscatecholamide ligands as sequestering agents for uranyl decorporation

Zhang, Qingchun; Jin, Bo; Peng, Rufang; Shan, Lei; Chu, Shijin

doi:10.1016/j.poly.2014.12.002

Cited by 9 publications

(4 citation statements)

References 29 publications

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“…Chelation of UO 2 2+ has been the subject of intense investigation over the last several decades primarily in the context of environmental and energy applications. For example, numerous studies have reported ligands for the extraction or sequestration of uranium from aqueous solution. − With respect to chelation of this ion in biological settings, there have also been extensive research efforts to develop ligands as decorporation agents for the removal of toxic concentrations of UO 2 2+ from the body. − A feature shared by many of these ligands is the presence of hard oxygen-donor atoms to maximally stabilize the highly oxophilic uranium center. To date, only one study has reported ligands specifically investigated for the implementation of 230 U in TAT.…”

Section: Introductionmentioning

confidence: 99%

Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for ²³⁰U Targeted α-Therapy

et al. 2022

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Uranium-230 is an α-emitting radionuclide with favorable properties for use in targeted α-therapy (TAT), a type of nuclear medicine that harnesses α particles to eradicate cancer cells. To successfully implement this radionuclide for TAT, a bifunctional chelator that can stably bind uranium in vivo is required. To address this need, we investigated the acyclic ligands H 2 dedpa, H 2 CHXdedpa, H 2 hox, and H 2 CHXhox as uranium chelators. The stability constants of these ligands with UO 2 2+ were measured via spectrophotometric titrations, revealing log β ML values that are greater than 18 and 26 for the "pa" and "hox" chelators, respectively, signifying that the resulting complexes are exceedingly stable. In addition, the UO 2 2+ complexes were structurally characterized by NMR spectroscopy and X-ray crystallography. Crystallographic studies reveal that all six donor atoms of the four ligands span the equatorial plane of the UO 2 2+ ion, giving rise to coordinatively saturated complexes that exclude solvent molecules. To further understand the enhanced thermodynamic stabilities of the "hox" chelators over the "pa" chelators, density functional theory (DFT) calculations were employed. The use of the quantum theory of atoms in molecules revealed that the extent of covalency between all four ligands and UO 2 2+ was similar. Analysis of the DFT-computed ligand strain energy suggested that this factor was the major driving force for the higher thermodynamic stability of the "hox" ligands. To assess the suitability of these ligands for use with 230 U TAT in vivo, their kinetic stabilities were probed by challenging the UO 2 2+ complexes with the bone model hydroxyapatite (HAP) and human plasma. All four complexes were >95% stable in human plasma for 14 days, whereas in the presence of HAP, only the complexes of H 2 CHXdedpa and H 2 hox remained >80% intact over the same period. As a final validation of the suitability of these ligands for radiotherapy applications, the in vivo biodistribution of their UO 2 2+ complexes was determined in mice in comparison to unchelated [UO 2 (NO 3 ) 2 ]. In contrast to [UO 2 (NO 3 ) 2 ], which displays significant bone uptake, all four ligand complexes do not accumulate in the skeletal system, indicating that they remain stable in vivo. Collectively, these studies suggest that the equatorial-spanning ligands H 2 dedpa, H 2 CHXdedpa, H 2 hox, and H 2 CHXhox are highly promising candidates for use in 230 U TAT.

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Section: Introductionmentioning

confidence: 99%

Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for ²³⁰U Targeted α-Therapy

et al. 2022

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“…After evaporation of the solvent, the residue was purified by flash column chromatography. Then deprotection of the hydroxyl groups under H 2 and Pd/C catalytic conditions in THF resulted in the -diketonates biscatecholamide ligands H 4 L 1-3 [6].…”

Section: Synthesis Of the Ligandsmentioning

confidence: 99%

“…Nevertheless, the characteristics of organic ligands play a key role in formation process of the uranyl complexes. Multidentates -diketonates biscatecholamide ligands [6] have six binding sites due to the O-donor of catechol aromatic ring anddiketonates [7,8]. As an important chelator for decorporation of uranyl ion, catechol has the favorable stability constant [9,10].…”

Section: Introductionmentioning

confidence: 99%

“…The -diketonates compounds were adequate sensitizers to luminescent lanthanide complexes in which either visible or NIR emission is consecutive with photoinduced energy transfer from the sensitizing ligand [11]. The -diketonates catecholamide ligands (H 4 L 1-3 ) have been reported as efficient uranyl sequestration agents in neutral pH aqueous media [6], but the detailed functional properties of their uranyl complexes have not been studied.…”

Section: Introductionmentioning

confidence: 99%

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Investigation on the Synthesis and Photocatalytic Property of Uranyl Complexes of the β-Diketonates Biscatecholamide Ligand

Zhang

Jin

Peng

et al. 2017

International Journal of Photoenergy

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A series of uranyl complexes have been synthesized by reacting hexadentate ligands CH 2 [COO (CH 2 ) n CAM; = 2, 3, 4] 2 [CAM = 2,3-Ph(OH) 2 CONH] containing the catecholamide (CAM) group and -diketonates framework with uranyl nitrate. They were characterized by FTIR, UV-vis, 1 H NMR, XPS, TGA, and elemental analysis. The analysis revealed that oxygen atom of -diketonate did not bind to uranyl ion in complexes 1-3. The photocatalytic degradation properties of the target complexes for degradation of rhodamine B (RhB) were investigated. The result indicated that approximately 74%, 71%, and 67% RhB were degraded in the presence of complexes 1-3 after about 210 min, respectively. Consequently, complexes 1-3 have excellent photocatalytic degradation property.

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Chlorofullerene C₆₀Cl₆: A Precursor for Straightforward Preparation of Highly Water‐Soluble Poly‐hydroxypyridinone Fullerene Derivatives as Potential Radionuclide Chelators

et al. 2017

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Radionuclide internal contamination can induce chemical and radiological intoxication and produce harmful free radicals in vivo. Conventional studies on chelating agents have disregarded the damage of free radicals to the body. Therefore, novel poly‐hydroxypyridinone fullerene derivatives were designed and prepared by using chlorofullerene as precursor. The poor water solubility of fullerene was ameliorated by chemically modifying of hydrophilic hydroxypyridinone, and obtaining high Water‐soluble fullerene derivatives. The radical scavenging reaction kinetics of target products were studied. They all exhibited much higher rate constants than other fullerene polymer system. The CeIII ion was used as a simulated radionuclide for evaluating the binding ability of target products, and the values of conditional stability constants were about 5.15‐6.11. Thus, the bifunctional, Water‐soluble fullerene derivatives were successfully generated. The results provided basis for further study on the potential application of poly‐hydroxypyridinone fullerene derivatives as radionuclide chelators.

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Symmetrical 1,3-dicarbonyl biscatecholamide ligands as sequestering agents for uranyl decorporation

Cited by 9 publications

References 29 publications

Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for ²³⁰U Targeted α-Therapy

Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for ²³⁰U Targeted α-Therapy

Investigation on the Synthesis and Photocatalytic Property of Uranyl Complexes of the β-Diketonates Biscatecholamide Ligand

Chlorofullerene C₆₀Cl₆: A Precursor for Straightforward Preparation of Highly Water‐Soluble Poly‐hydroxypyridinone Fullerene Derivatives as Potential Radionuclide Chelators

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Symmetrical 1,3-dicarbonyl biscatecholamide ligands as sequestering agents for uranyl decorporation

Cited by 9 publications

References 29 publications

Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for 230U Targeted α-Therapy

Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for 230U Targeted α-Therapy

Investigation on the Synthesis and Photocatalytic Property of Uranyl Complexes of the β-Diketonates Biscatecholamide Ligand

Chlorofullerene C60Cl6: A Precursor for Straightforward Preparation of Highly Water‐Soluble Poly‐hydroxypyridinone Fullerene Derivatives as Potential Radionuclide Chelators

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Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for ²³⁰U Targeted α-Therapy

Stable Chelation of the Uranyl Ion by Acyclic Hexadentate Ligands: Potential Applications for ²³⁰U Targeted α-Therapy

Chlorofullerene C₆₀Cl₆: A Precursor for Straightforward Preparation of Highly Water‐Soluble Poly‐hydroxypyridinone Fullerene Derivatives as Potential Radionuclide Chelators