3-acetyl-coumarin-substituted thiosemicarbazones and their ruthenium, rhodium and iridium metal complexes: An investigation of the antibacterial, antioxidant and cytotoxicity activities

Nongpiur, Carley Giffert L.; Soh, Charlestine; Diengdoh, Danny F; Verma, Akalesh Kumar; Gogoi, Renu; Banothu, Venkanna; Kaminsky, Werner; Kollipara, Mohan Rao

doi:10.1016/j.jorganchem.2023.122788

Cited by 6 publications

(3 citation statements)

References 52 publications

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“…In addition, the antioxidant abilities of coumarin metal complexes to scavenge free radicals recently has been reported in an excellent review [ 50 ]. Furthermore, several reports of coumarin-based bioinorganic compounds include phenylselenyl derivatives that act as sensors for selective detection of superoxide [ 51 ] as well as ruthenium coumarin complexes which scavenge superoxide and DPPH radicals [ 52 ] and other coumarin metal complexes made with ruthenium, rhodium and iridium showing antioxidant activity [ 53 ].…”

Section: Discussionmentioning

confidence: 99%

Examining the Antioxidant and Superoxide Radical Scavenging Activity of Anise, (Pimpinella anisum L. Seeds), Esculetin, and 4-Methyl-Esculetin Using X-ray Diffraction, Hydrodynamic Voltammetry and DFT Methods

Rossi,

Caruso,

Thieke

et al. 2023

Pharmaceuticals

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Pimpinella anisum L., or anise, is a plant that, besides its nutritional value, has been used in traditional medical practices and described in many cultures in the Mediterranean region. A possible reason for anise’s therapeutic value is that it contains coumarins, which are known to have many biomedical and antioxidant properties. HPLC analysis in our laboratory of the anise extract shows the presence of the coumarin esculetin. We used a hydrodynamic voltammetry rotating ring–disk electrode (RRDE) method to measure the superoxide scavenging abilities of anise seeds and esculetin, which has marked scavenging activity. A related coumarin, 4-methyl-esculetin, also showed strong antioxidant activity as measured by RRDE. Moreover, this study includes the X-ray crystal structure of esculetin and 4-methyl-esculetin, which reveal the H-bond and the stacking intermolecular interactions of the two coumarins. Coordinates of esculetin crystal structure were used to perform a DFT study to arrive at the mechanism of superoxide scavenging. Besides performing a H(hydroxyl) abstraction in esculetin position 6 by superoxide, the scavenging also includes the presence of a second superoxide radical in a π–π approach. Both rings of esculetin were explored for this attack, but only the pyrone ring was effective. As a result, one product of esculetin scavenging is H2O2 formation, while the second superoxide remains π–π trapped within the pyrone ring to form an esculetin-η-O2 complex. Comparison with other coumarins shows that subtle structural differences in the coumarin framework can imply marked differences in scavenging. For instance, when the catechol moiety of esculetin (position 6,7) is shifted to position 7,8 in 4-methyl-7,8-dihydroxy coumarin, that coumarin shows a superoxide dismutase action, which, beside H2O2 formation, includes the formation and elimination of a molecule of O2. This is in contrast with the products formed through esculetin superoxide scavenging, where a second added superoxide remains trapped, and forms an esculetin-η-O2 complex.

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Section: Discussionmentioning

confidence: 99%

Examining the Antioxidant and Superoxide Radical Scavenging Activity of Anise, (Pimpinella anisum L. Seeds), Esculetin, and 4-Methyl-Esculetin Using X-ray Diffraction, Hydrodynamic Voltammetry and DFT Methods

Rossi,

Caruso,

Thieke

et al. 2023

Pharmaceuticals

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“…In this context, the past few decades have witnessed extensive exploration into several hundred transition metal complexes, featuring elements such as Au, Ru, Ir, and others. More recently, rhodium complexes have garnered heightened attention due to their diverse biological activities, such as antibacterial, antioxidant, antifungal, anti-inflammatory, and antithrombotic activity, encompassing a wide spectrum of molecular targets. The pioneering endeavors of esteemed researchers, including Sheldrick, Dyson, Pandey, Ma, and Leung, have yielded significant advancements in the development of novel rhodium-based complexes, exhibiting promising anticancer attributes.…”

Section: Introductionmentioning

confidence: 99%

Rhodium(I) Complexes Containing the N^N^N-Chelating Ligand: Synthesis, Structure, and Biological Activity

Liang,

Huang,

et al. 2024

Organometallics

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Rhodium complexes have garnered extensive attention owing to their inherent potential for biological activity. The catalytic properties of Rh−N^N^N complexes have been investigated extensively, whereas there is a paucity of studies regarding their antitumor activity. In this study, we present four rhodium(I) complexes, each distinguished by a different anion. These complexes incorporate 2,6-bis(1,5-diphenyl-1H-pyrazol-3yl)pyridine as the tridentate N^N^N-chelating ligand and one carbonyl ligand. These complexes underwent rigorous evaluation for cytotoxicity against a spectrum of human tumor cell lines, including MCF-7, HeLa, and HepG2, alongside a nontumor cell line, HUVEC, employing MTT assays and flow cytometry. Our results unveiled that complex 1 Rh(N^N^N)(CO)Cl exhibited remarkable cytotoxicity and demonstrated a favorable selectivity index against tumor cells, with a particularly notable impact on breast adenocarcinoma (selectivity index = 5.2). To further ascertain its potential utility, we probed the interactions between complex 1 and ctDNA/BSA. Both UV and fluorescence scan data indicated that complex 1 was able to intercalate into ctDNA and bind with BSA. Meanwhile, comprehensive assessments, encompassing the mobility shift assay and the micronucleus test, consistently showed that complex 1 could not induce DNA fragmentation in vitro and the formation of micronucleus in mouse erythrocytes. All of these findings suggest that complex 1 could be a promising antitumor compound.

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“…Our particular interest to rhodium complexes stems partly from our experience in rhodium chemistry 82–84 and partly from appealing properties this metal shows in the C–H bond activation and catalysis, 85–91 photochemistry 92–107 and bioinorganic chemistry. 108–128 Along with the synthesis of HL 2,5 and HL 2,6 and their rhodium( iii ) complexes [RhL 2,5 (Solv)Cl 2 ]· n EtOH and [RhL 2,6 (Solv)Cl 2 ]· n EtOH , here we report the impact of isomerism on molecular and supramolecular structures of these compounds, on the photophysical properties of the rhodium( iii ) complexes and on the cytotoxic activity of the ligands and complexes. These experimental studies are supplemented by the theoretical investigation of photophysical properties of the complexes and by theoretical modelling of the sp 2 C–H bond activation which occurs upon the coordination of HL 2,5 and HL 2,6 to RhCl 3 .…”

Section: Introductionmentioning

confidence: 99%

N^N^C-Cyclometalated rhodium(iii) complexes with isomeric pyrimidine-based ligands: unveiling the impact of isomerism on structural motifs, luminescence and cytotoxicity

Vorobyeva,

Bautina,

Shekhovtsov

et al. 2024

Dalton Trans.

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3-acetyl-coumarin-substituted thiosemicarbazones and their ruthenium, rhodium and iridium metal complexes: An investigation of the antibacterial, antioxidant and cytotoxicity activities

Cited by 6 publications

References 52 publications

Examining the Antioxidant and Superoxide Radical Scavenging Activity of Anise, (Pimpinella anisum L. Seeds), Esculetin, and 4-Methyl-Esculetin Using X-ray Diffraction, Hydrodynamic Voltammetry and DFT Methods

Examining the Antioxidant and Superoxide Radical Scavenging Activity of Anise, (Pimpinella anisum L. Seeds), Esculetin, and 4-Methyl-Esculetin Using X-ray Diffraction, Hydrodynamic Voltammetry and DFT Methods

Rhodium(I) Complexes Containing the N^N^N-Chelating Ligand: Synthesis, Structure, and Biological Activity

N^N^C-Cyclometalated rhodium(iii) complexes with isomeric pyrimidine-based ligands: unveiling the impact of isomerism on structural motifs, luminescence and cytotoxicity

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