Crystal structures and supramolecular architectures of ONO donor hydrazone and solvent exchangeable dioxidomolybdenum(VI) complexes derived from 3,5-diiodosalicyaldehyde-4-methoxybenzoylhydrazone: Hirshfeld surface analysis and interaction energy calculations

Kuriakose, Daly; Kurup, M.R. Prathapachandra

doi:10.1016/j.poly.2019.06.041

Cited by 19 publications

(8 citation statements)

References 54 publications

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“…In overwhelming majority of the solid halogen-bonded POMs, monovalent halogen-containing compounds were used as XB donors, 44,[84][85][86][87][88] while pairing between POMs and iodonium salts, exhibiting double -(I III )-hole site, is very little studied and only two relevant reports appeared in the literature. The first one has been focused on UV induced polymerization, in which the added POMs assisted the generation of phenyl radicals from corresponding iodonium salts.…”

Section: Halogen-bonded Pomsmentioning

confidence: 99%

Key-to-Lock Halogen Bond-Based Tetragonal Pyramidal Association of Iodonium Cations with the Lacune Rims of Beta-Octamolybdate

Soldatova,

Radzhabov,

Ivanov

et al. 2024

Preprint

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The structure-directing “key-to-lock” interaction of double -(I(III))-hole donating iodonium cations with the O-flanked pseudo-lacune rims of [β-Mo8O26]4– gives halogen-bonded iodonium–beta-octamolybate supramolecular associates. In the occurrence of their tetragonal pyramidal motifs, deep and broad -(I(III))-holes of a cation recognize the molybdate backbone, which provides an electronic pool localized around the two lacunes. The halogen-bonded I∙∙∙O linkages in the structures were thoroughly studied computationally and classified as two-center, three-center bifurcated, and unconventional “orthogonal” I∙∙∙O halogen bonds. In the latter, the O-atom approaches orthogonally the C–I(III)–C plane of an iodonium cation and this geometry diverge from the IUPAC criteria for the identification of the halogen bond

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Section: Halogen-bonded Pomsmentioning

confidence: 99%

Key-to-Lock Halogen Bond-Based Tetragonal Pyramidal Association of Iodonium Cations with the Lacune Rims of Beta-Octamolybdate

Soldatova,

Radzhabov,

Ivanov

et al. 2024

Preprint

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“…The acylhydrazones can form intermolecular hydrogen bonds through the hydrogen atom bound to the amino nitrogen (-NH-) and the oxygen atom [18][19][20], between the hydrogen atom bound to the imine carbon (CH) and the atomic nitrogen atom (-N=) of another molecule [20]. The acylhydrazones exhibit geometric isomerism due to the imine group (-N=CH-).…”

Section: Structurementioning

confidence: 99%

Acylhydrazones and Their Biological Activity: A Review

et al. 2022

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Due to the structure of acylhydrazones both by the pharmacophore –CO–NH–N= group and by the different substituents present in the molecules of compounds of this class, various pharmacological activities were reported, including antitumor, antimicrobial, antiviral, antiparasitic, anti-inflammatory, immunomodulatory, antiedematous, antiglaucomatous, antidiabetic, antioxidant, and actions on the central nervous system and on the cardiovascular system. This fragment is found in the structure of several drugs used in the therapy of some diseases that are at the top of public health problems, like microbial infections and cardiovascular diseases. Moreover, the acylhydrazone moiety is present in the structure of some compounds with possible applications in the treatment of other different pathologies, such as schizophrenia, Parkinson’s disease, Alzheimer’s disease, and Huntington’s disease. Considering these aspects, we consider that a study of the literature data regarding the structural and biological properties of these compounds is useful.

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“…In continuation of our research on the pharmacological properties of various transition metal complexes, ,,− herein the synthesis of two monomeric, [MoO 2 (L 1 )(MeOH)] ( 1 ) and [MoO 2 (L 2 )(EtOH)] ( 2 ), and two mixed-ligand dimeric, [{MoO 2 (L 1–2 )} 2 (μ-4,4′-bipy)] ( 3 and 4 ), dioxidomolybdenum(VI) complexes from two aroylhydrazone ligands (H 2 L 1–2 ) is reported. The complexes revealed a distorted octahedral geometry with the sixth labile coordination site occupied by the solvent molecule (MeOH/EtOH) in case of the monomeric complexes and the coligand 4,4′-bipyridine in case of the dimeric complexes. − Hydrazones are important set of ligands, as they manifests a vast range of pharmaceutical activities. − It has been demonstrated that their biological properties are considerably enhanced upon complexation to metal ions . Moreover, the incorporation of coligands with powerful σ donor functions, such as 4,4′-bipyridine might affect the planarity, hydrophobicity, and general anticancer action of metal complexes. , The interaction of the synthesized compounds with human serum albumin (HSA) and CT DNA has been studied with the combined application of instrumental and computational methods.…”

Section: Introductionmentioning

confidence: 99%

Mo(VI) Potential Metallodrugs: Explaining the Transport and Cytotoxicity by Chemical Transformations

et al. 2022

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The transport and cytotoxicity of molybdenum-based drugs have been explained with the concept of chemical transformation, a very important idea in inorganic medicinal chemistry that is often overlooked in the interpretation of the biological activity of metal-containing systems. Two monomeric, [MoO2(L1)(MeOH)] (1) and [MoO2(L2)(EtOH)] (2), and two mixed-ligand dimeric MoVIO2 species, [{MoO2(L1–2)}2(μ-4,4′-bipy)] (3–4), were synthesized and characterized. The structures of the solid complexes were solved through SC-XRD, while their transformation in water was clarified by UV–vis, ESI-MS, and DFT. In aqueous solution, 1–4 lead to the penta-coordinated [MoO2(L1–2)] active species after the release of the solvent molecule (1 and 2) or removal of the 4,4′-bipy bridge (3 and 4). [MoO2(L1–2)] are stable in solution and react with neither serum bioligand nor cellular reductants. The binding affinity of 1–4 toward HSA and DNA were evaluated through analytical and computational methods and in both cases a non-covalent interaction is expected. Furthermore, the in vitro cytotoxicity of the complexes was also determined and flow cytometry analysis showed the apoptotic death of the cancer cells. Interestingly, μ-4,4′-bipy bridged complexes 3 and 4 were found to be more active than monomeric 1 and 2, due to the mixture of species generated, that is [MoO2(L1–2)] and the cytotoxic 4,4′-bipy released after their dissociation. Since in the cytosol neither the reduction of MoVI to MoV/IV takes place nor the production of reactive oxygen species (ROS) through Fenton-like reactions of 1–4 with H2O2 occurs, the mechanism of cytotoxicity should be attributable to the direct interaction with DNA that happens with a minor-groove binding which results in cell death through an apoptotic mechanism.

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Crystal structures and supramolecular architectures of ONO donor hydrazone and solvent exchangeable dioxidomolybdenum(VI) complexes derived from 3,5-diiodosalicyaldehyde-4-methoxybenzoylhydrazone: Hirshfeld surface analysis and interaction energy calculations

Cited by 19 publications

References 54 publications

Key-to-Lock Halogen Bond-Based Tetragonal Pyramidal Association of Iodonium Cations with the Lacune Rims of Beta-Octamolybdate

Key-to-Lock Halogen Bond-Based Tetragonal Pyramidal Association of Iodonium Cations with the Lacune Rims of Beta-Octamolybdate

Acylhydrazones and Their Biological Activity: A Review

Mo(VI) Potential Metallodrugs: Explaining the Transport and Cytotoxicity by Chemical Transformations

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