Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1<i>H</i>-pyrazole

Fernández, Belén; Fernández, Ignacio; Cepeda, Javier; Medina-O'Donnell, Marta; Rufino‐Palomares, Eva E.; Raya-Barón, Álvaro; Gómez‐Ruiz, Santiago; Pérez‐Jiménez, Amalia; Lupiáñez, José A.; Reyes‐Zurita, Fernando J.; Rodríguez-Diéguez, Antonio

doi:10.1021/acs.cgd.7b01443

Cited by 33 publications

(11 citation statements)

References 45 publications

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“…A series of metal-organic chains (MOCs) based on 4-nitro-1 H -pyrazole as ligand and zinc as metal center has been reported and structurally characterized [ 212 ]. The antitumor properties of the 4-nitro-1 H -pyrazole ligand ( HL 40 ) and the MOCs complexes 40a ({[Zn 2 (μ-4-NO 2 -pz) 3 (μ-OH)]·H 2 O} n ), 40b ({[Zn 2 (μ-4-NO 2 -pz) 4 ]} n ) and 40c ({[Zn 3 (μ-4-NO 2 -pz) 4 (μ-ac) 2 (H 2 O) 2 ]} n ) ( Figure 21 ) were evaluated against three cancer cell lines (HT29, Hep-G2 and B16-F10).…”

Section: Miscellanea Systemsmentioning

confidence: 99%

“…The s Table 1 D Zn-coordination complexes 40b and 40c showed a similar antitumor activity (average IC 50 48.23 and 45.13 μg/mL for 40b and 40c respectively), lower IC 50 than the free ligand (average IC 50 136.67 μg/mL), and with low specificity with respect to cell type ( Table 11 ). MOCs complexes 40b and 40c , prepared using water as solvent, can avoid the potential self-aggregation issue often encountered by some antitumor compounds such as triterpenes and minimize generic interactions, representing an alternative to traditional coordination complexes [ 212 ].…”

Section: Miscellanea Systemsmentioning

confidence: 99%

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Zinc Complexes with Nitrogen Donor Ligands as Anticancer Agents

et al. 2020

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The search for anticancer metal-based drugs alternative to platinum derivatives could not exclude zinc derivatives due to the importance of this metal for the correct functioning of the human body. Zinc, the second most abundant trace element in the human body, is one of the most important micro-elements essential for human physiology. Its ubiquity in thousands of proteins and enzymes is related to its chemical features, in particular its lack of redox activity and its ability to support different coordination geometries and to promote fast ligands exchange. Analogously to other trace elements, the impairment of its homeostasis can lead to various diseases and in some cases can be also related to cancer development. However, in addition to its physiological role, zinc can have beneficial therapeutic and preventive effects on infectious diseases and, compared to other metal-based drugs, Zn(II) complexes generally exert lower toxicity and offer few side effects. Zinc derivatives have been proposed as antitumor agents and, among the great number of zinc coordination complexes which have been described so far, this review focuses on the design, synthesis and biological studies of zinc complexes comprising N-donor ligands and that have been reported within the last five years.

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Section: Miscellanea Systemsmentioning

confidence: 99%

Section: Miscellanea Systemsmentioning

confidence: 99%

Zinc Complexes with Nitrogen Donor Ligands as Anticancer Agents

et al. 2020

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“…Traditionally, small organic molecules have been described with anti-cancer and anti-inflammatory properties useful as drugs [44,45]. Currently, has been reported that metal complexes possess remarkable advantages that render them as attractive alternatives to small organic molecules for the development of potential therapeutic agents, among others they show higher half-lives to allow their preferential tissue accumulation, due to their highest vascular permeability that permits their retention on tumor tissues [46].…”

Section: Raw 2647 Cell Viabilitymentioning

confidence: 99%

Designing Single-Molecule Magnets as Drugs with Dual Anti-Inflammatory and Anti-Diabetic Effects

Navas

Jannus

Fernández

et al. 2020

IJMS

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We have designed and synthesized two novel cobalt coordination compounds using bumetanide (bum) and indomethacin (ind) therapeutic agents. The anti-inflammatory effects of cobalt metal complexes with ind and bum were assayed in lipopolysaccharide stimulated RAW 264.7 macrophages by inhibition of nitric oxide production. Firstly, we determined the cytotoxicity and the anti-inflammatory potential of the cobalt compounds and ind and bum ligands in RAW 264.7 cells. Indomethacin-based metal complex was able to inhibit the NO production up to 35% in a concentration-dependent manner without showing cytotoxicity, showing around 6–37 times more effective than indomethacin. Cell cycle analysis showed that the inhibition of NO production was accompanied by a reversion of the differentiation processes in LPS-stimulated RAW 264.7 cells, due to a decreased of cell percentage in G0/G1 phase, with the corresponding increase in the number of cells in S phase. These two materials have mononuclear structures and show slow relaxation of magnetization. Moreover, both compounds show anti-diabetic activity with low in vitro cell toxicities. The formation of metal complexes with bioactive ligands is a new and promising strategy to find new compounds with high and enhanced biochemical properties and promises to be a field of great interest.

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“…Metal complexes bearing triazole ligands are also considered one of the most biologically active materials. These complexes can be utilized in various agricultural and pharmaceutical applications because their activity can be easily tuned by varying metals, ancillary ligands, and coordination geometries. − Particularly, zinc (Zn) complexes have been extensively investigated due to their chemical stability and physiological merits. − Zinc ions exist in many chemical and biological systems as Zn 2+ species with a d 10 configuration, making them difficult to either oxidize or reduce. Since Zn 2+ ions can act as Lewis acids, they have a strong tendency to form stable adducts with triazole ligands.…”

Section: Introductionmentioning

confidence: 99%

Triazole-Bridged Zinc Dinuclear Complexes: Mechanochemical Synthesis, Crystal Structure, and Biological Activity

et al. 2022

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Two zinc (Zn) complexes, [Zn2(DAT)2Cl4] (I) and [Zn2(DAT)2(NO3)4] (II), were prepared by grinding 3,5-diamino-1,2,4-triazole (C2H5N5, DAT) with Zn precursors such as ZnCl2 and Zn(NO3)2, respectively. This solid-state reaction gives the corresponding Zn complex as the sole product in over 99% yield. This mechanochemical method promotes the selective formation of Zn complexes different from those obtained using the conventional solution-based route. The crystal structures of the two complexes were analyzed by single-crystal X-ray diffraction. Complex (I) crystallizes in the monoclinic space group P21/c, whereas complex (II) crystallizes in the triclinic space group P 1̅. Each complex is characterized by the presence of a characteristic DAT-bridged dimer with one DAT ligand per Zn atom, and the DAT ligand provides a bridge between the two Zn metals. All Zn centers of (I) and (II) adopted a slightly distorted tetrahedral geometry. Both complexes contain a hexanuclear Zn2N4 ring, but their ring structures are different. Complex (I) possesses a boat geometry, while complex (II) has a nearly planar structure. The Zn-bound chlorides of complex (I) form intermolecular N–H···Cl hydrogen bonds that link neighboring molecules. In complex (II), the O atoms in the nitrate groups are hydrogen-bonded to the DAT ligand via O···H–N linkages. Both complexes exhibit blue emissions in the solid state at ambient temperature. They were evaluated as anticancer agents in HeLa, NCCIT, and MCF-7 cancer cell lines, exhibiting promising anticancer activities.

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Modulating Anticancer Potential by Modifying the Structural Properties of a Family of Zinc Metal–Organic Chains Based on 4-Nitro-1H-pyrazole

Cited by 33 publications

References 45 publications

Zinc Complexes with Nitrogen Donor Ligands as Anticancer Agents

Zinc Complexes with Nitrogen Donor Ligands as Anticancer Agents

Designing Single-Molecule Magnets as Drugs with Dual Anti-Inflammatory and Anti-Diabetic Effects

Triazole-Bridged Zinc Dinuclear Complexes: Mechanochemical Synthesis, Crystal Structure, and Biological Activity

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