Complexation of environmentally and biologically relevant metals with bifunctional 3-hydroxy-4-pyridinones

Irto, Anna; Cardiano, Paola; Chand, Karam; Cigala, Rosalia Maria; Crea, Francesco; Stefano, Concetta De; Gattuso, Giuseppe; Sammartano, Silvio; Santos, M. Amélia

doi:10.1016/j.molliq.2020.114349

Cited by 17 publications

(11 citation statements)

References 55 publications

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“…Bifunctional 3-hydroxy-4-pyridinones ( L1 – L5 , Figure 2 ), featured by a single 3,4-HP chelating core and various functional groups attached to the pyridinone moiety by different N -alkyl spacers, were synthesized and thermodynamically evaluated as possible strong chelators of hard metal cations of environmental relevance (Al 3+ , Fe 3+ ) [ 7 , 8 ], using potentiometric and spectrophotometric techniques; the potential thermodynamic competition, and eventually depletion, of other hard (Ca 2+ , Mg 2+ ) and borderline (Zn 2+ , Cu 2+ ) character metals of environmental interest was also evaluated [ 8 , 9 , 10 ]. The main experimental conditions chosen by the authors was I = 0.15 M in NaCl (aq) and T = 298.15 K. Sodium chloride was selected as ionic medium, since it is the main inorganic constituent of many natural fluids [ 11 , 12 ], or it can also be found in soils as contaminant (saline soils) [ 13 ].…”

Section: Mono- and Bis-(3-hydroxy-4-pyridinone) Ligandsmentioning

confidence: 99%

Hydroxypyridinone-Based Metal Chelators towards Ecotoxicity: Remediation and Biological Mechanisms

et al. 2022

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Hydroxypyridinones (HPs) are recognized as excellent chemical tools for engineering a diversity of metal chelating agents, with high affinity for hard metal ions, exhibiting a broad range of activities and applications, namely in medical, biological and environmental contexts. They are easily made and functionalizable towards the tuning of their pharmacokinetic properties or the improving of their metal complex thermodynamic stabilities. In this review, an analysis of the recently published works on hydroxypyridinone-based ligands, that have been mostly addressed for environmental applications, namely for remediation of hard metal ion ecotoxicity in living beings and other biological matrices is carried out. In particular, herein the most recent developments in the design of new chelating systems, from bidentate mono-HP to polydentate multi-HP derivatives, with a structural diversity of soluble or solid-supported backbones are outlined. Along with the ligand design, an analysis of the relationship between their structures and activities is presented and discussed, namely associated with the metal affinity and the thermodynamic stability of the corresponding metal complexes.

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Section: Mono- and Bis-(3-hydroxy-4-pyridinone) Ligandsmentioning

confidence: 99%

Hydroxypyridinone-Based Metal Chelators towards Ecotoxicity: Remediation and Biological Mechanisms

et al. 2022

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“…The exceptional photophysical properties of rhodamines can be complemented with the introduction of receptors, such as 3-hydroxy-4-pyridinone (3,4-HPO) units, allowing the optical detection of several species, namely M(II) and M(III) metal ions [ 15 ]. Indeed, 3,4-HPOs are an important class of N -heterocyclic bidentate ligands, whose use has been widely explored as specific and selective chelators towards environmentally and biologically relevant metals, specially Al 3+ and Fe 3+ [ 16 , 17 , 18 , 19 ]. In this context, the functionalization at the benzoate ring of rhodamine with 3,4-HPO chelating units is being approached as a very promising and useful methodology to obtain fluorescent probes, which can be used in the detection and quantification of such metal ions [ 15 , 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

“…Indeed, 3,4-HPOs are an important class of N -heterocyclic bidentate ligands, whose use has been widely explored as specific and selective chelators towards environmentally and biologically relevant metals, specially Al 3+ and Fe 3+ [ 16 , 17 , 18 , 19 ]. In this context, the functionalization at the benzoate ring of rhodamine with 3,4-HPO chelating units is being approached as a very promising and useful methodology to obtain fluorescent probes, which can be used in the detection and quantification of such metal ions [ 15 , 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Functionalization of Rhodamine Platforms with 3-Hydroxy-4-pyridinone Chelating Units and Its Fluorescence Behavior towards Fe(III)

et al. 2022

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Functionalization of xanthene fluorophores with specific receptor units is an important topic of research aiming for the development of new analytical tools for biological sciences, clinical diagnosis, food and environmental monitoring. Herein, we report a new dihydrorosamine containing two active amino groups, which was functionalized with 3-benzyloxy-1-(3′-carboxypropyl)-2-methyl-4-pyridinone through an amide coupling strategy. Benzylated mono- and di-functionalized dihydrorosamine derivatives (H in position 9 of the xanthene) were obtained, but with modest reaction yields, requiring long and laborious purification procedures. Looking for a more efficient approach, rhodamine 110 was selected to react with the carboxypropyl pyridinone, enabling the isolation of the corresponding mono- and di-functionalized derivatives in amounts that depend on the excess of pyridinone added to the reaction. The structure of all compounds was established by 1H and 13C NMR, MS (ESI) and their absorption and emission properties were evaluated in dichloromethane. The fluorescence behavior of the debenzylated mono-rhodamine 110 derivative in the presence of Fe(III) was studied, making it an interesting fluorogenic dye for future optical sensing applications.

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“…In this light, many research efforts have been devoted to the development of new strategies aimed to remove metals from different matrices without side effects. All the green and sustainable approaches developed for metals extraction from environmental matrices are called “ chelation technologies ” [ 11 ], whereas the treatment of human diseases related to the metal intoxication is called “ chelation therapy ”. This last approach is based on the administration of chelating agents to patients suffering from metals overload, inducing their sequestration and systemic excretion [ 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

Bifunctional 3-Hydroxy-4-Pyridinones as Potential Selective Iron(III) Chelators: Solution Studies and Comparison with Other Metals of Biological and Environmental Relevance

et al. 2021

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The binding ability of five bifunctional 3-hydroxy-4-pyridinones towards Cu2+ and Fe3+ was studied by means of potentiometric and UV–Vis spectrophotometric measurements carried out at I = 0.15 mol L−1 in NaCl(aq),T = 298.15 K and 310.15 K. The data treatments allowed us to determine speciation schemes featured by metal-ligand species with different stoichiometry and stability, owing to the various functional groups present in the 3-hydroxy-4-pyridinones structures, which could potentially participate in the metal complexation, and in the Cu2+ and Fe3+ behaviour in aqueous solution. Furthermore, the sequestering ability and metal chelating affinity of the ligands were investigated by the determination of pL0.5 and pM parameters at different pH conditions. Finally, a comparison between the Cu2+ and Fe3+/3-hydroxy-4-pyridinones data herein presented with those already reported in the literature on the interaction of Zn2+ and Al3+ with the same ligands showed that, from the thermodynamic point of view, the 3-hydroxy-4-pyridinones are particularly selective towards Fe3+ and could therefore be considered promising iron-chelating agents, also avoiding the possibility of competition, and eventually the depletion, of essential metal cations of biological and environmental relevance, such as Cu2+ and Zn2+.

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Complexation of environmentally and biologically relevant metals with bifunctional 3-hydroxy-4-pyridinones

Cited by 17 publications

References 55 publications

Hydroxypyridinone-Based Metal Chelators towards Ecotoxicity: Remediation and Biological Mechanisms

Hydroxypyridinone-Based Metal Chelators towards Ecotoxicity: Remediation and Biological Mechanisms

Functionalization of Rhodamine Platforms with 3-Hydroxy-4-pyridinone Chelating Units and Its Fluorescence Behavior towards Fe(III)

Bifunctional 3-Hydroxy-4-Pyridinones as Potential Selective Iron(III) Chelators: Solution Studies and Comparison with Other Metals of Biological and Environmental Relevance

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