Synthesis and anticancer evaluation of copper(II)- and manganese(II)- theophylline mixed ligand complexes

Gordon, Allen; Abosede, Olufunso O.; Ntsimango, Songeziwe; Hosten, Eric C.; Myeza, Nonzuzo; Eyk, Armorel van; Harmse, Leonie; Ogunlaja, Adeniyi S.

doi:10.1016/j.poly.2022.115649

Cited by 15 publications

(10 citation statements)

References 62 publications

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“…From the TGA/DSC plots, the first stage of weight loss occurs between 100 °C and 150 °C, is attributed to the loss of water molecules weakly bound to the materials [40] . The second and third stage of decomposition were observed between 300 °C to 800 °C in all the complexes and results from the complete decomposition of the dipicoliamide ligands to form MnO 2 [41] . The three main exothermic events corresponding to the various stages of weight loss occurred between 100 °C and 400 °C.…”

Section: Resultsmentioning

confidence: 94%

“…[40] The second and third stage of decomposition were observed between 300 °C to 800 °C in all the complexes and results from the complete decomposition of the dipicoliamide ligands to form MnO 2 . [41] The three main exothermic events corresponding to the various stages of weight loss occurred between 100 °C and 400 °C. For example, the DSC curves of Mn1 showed strong endothermic peaks around 120 °C, 385 °C, and 450 °C, (Figures S29-S32).…”

Section: Thermal Stability Studies Of the Mn(ii) Complexesmentioning

confidence: 99%

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Novel Metallomacrocyclic Carboxamide Mn(II) Complexes as Efficient Catalysts for the Transfer Hydrogenation of Ketones

Kumah,

Migwi,

Schmitz

et al. 2023

ChemCatChem

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Herein, we present the first metallomacrocyclic Mn(II) complexes as efficient catalysts for the transfer hydrogenation of ketones. The dinuclear Mn(II) complexes [Mn2(L1–L4)2Cl2] (Mn1–Mn4), were synthesised in good yields by reacting MnCl2 ⋅ 4H2O with the ligands N,N′‐(1,4‐phenylene)dipicolinamide (L1), N,N′‐(1,2‐phenylene)dipicolinamide (L2), N,N′‐(4‐methoxy‐1,2‐phenylene)dipicolinamide (L3) and N,N′‐(4,5‐dimethyl‐1,2‐phenylene)dipicolinamide (L4). Structural characterization of the resulting Mn(II) complexes was achieved using FT‐IR spectroscopy, mass spectrometry, magnetic moment measurements, elemental analysis, and single‐crystal X‐ray diffraction for Mn2. The solid‐state structure of complex Mn2 reveals a dinuclear Mn(II) core, in which the metal coordination sphere consists of two bidentate, K2(N−O) bridging L2 units and two chlorido ligands to give a distorted octahedral geometry. The Mn(II) complexes (Mn1–Mn4) were quite active catalysts for the transfer hydrogenation of ketones displaying turnover numbers (TON) of up to 2633, which is comparable to those of well‐established Mn(I) catalysts. The new Mn(II) complexes also efficiently hydrogenated a number of aromatic, heterocyclic, functionalized and aliphatic ketones. More significantly, cheaper, and readily available hydrogen sources like ethanol also gave decent catalytic activities in the transfer hydrogenation reactions.

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Section: Resultsmentioning

confidence: 94%

Section: Thermal Stability Studies Of the Mn(ii) Complexesmentioning

confidence: 99%

Novel Metallomacrocyclic Carboxamide Mn(II) Complexes as Efficient Catalysts for the Transfer Hydrogenation of Ketones

Kumah,

Migwi,

Schmitz

et al. 2023

ChemCatChem

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“…A modified method from the literature was followed [ 42 ] by reacting a solution of two equivalents of 1,10-phenanthroline in ethanol–H 2 O (90:10) solution with one equivalent of CuCl 2 .H 2 O under reflux for 3 h. The solid precipitate formed upon completion was filtered off, and the filtrate was kept at room temperature and allowed to evaporate slowly, yielding high-quality greenish-purple crystals suitable for X-ray analysis. [Cu(phen) 2 Cl]: colour, purple; FT-IR (cm −1 ): 3355 v(OH), 3051 v(CH), 1628 v(C=N), 1584 v(C=N), and 485 v(Cu–N).…”

Section: Methodsmentioning

confidence: 99%

Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO2 to Synthesize α-Unsaturated Aminocarboxylic Acids

Gordon

Hosten²,

Ogunlaja³

2022

Pharmaceuticals

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Here, we report the Cu(II)-photocatalysed hydrocarboxylation of imines (C=N) from a series of synthesized Schiff Base derivatives, namely (E)-1-(4-((4-methylbenzylidene)amino)phenyl)ethanone, (E)-1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone, (E)-4-((5-bromo-2-hydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, and (E)-1,5-dimethyl-4-((4-methylbenzylidene)amino)-2-phenyl-1H-pyrazol-3(2H)-one, with carbon dioxide (CO2) to generate disubstituted amino acids. Under mild conditions (atmospheric pressure of CO2, room temperature, and 30 W Blue LED light), good to excellent yields confirming the formation of substituted amino acid unsaturated acid derivatives were obtained. Single crystal X-ray diffraction (SC-XRD) and UV-Vis diffuse reflectance spectroscopy (UV-Vis-DRS) confirmed the square pyramidal geometry of the Cu(II) photocatalyst. Docking and DFT calculations of the substituted amino acid unsaturated acid derivatives showed their potential as antimicrobial molecules.

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“…The compound CTP -Cu(theo) 2 phen(H 2 O)•5H 2 O -was prepared according to the methods described in the literature (Majodina et al 2021;Gordon et al 2022), diluted in dimethyl sulfoxide (DMSO) and stored at room temperature. The chemical structure of the test compound is shown in Fig.…”

Section: Test Compoundmentioning

confidence: 99%

Unveiling the Antifungal Mechanisms of CTP, a New Copper(II)- Theophylline/1,10-Phenanthroline Complex, on Drug-Resistant Non-albicans Candida Species

Frota,

Barbosa,

Lorentino

et al. 2024

Preprint

Self Cite

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Candida species are the commonest opportunistic human fungal pathogens worldwide, with Candida albicans serving as the primary representative. However, non-albicans Candida species (NACs) have been on the rise in terms of incidence, and they are associated with outbreaks and instances of antifungal resistance. The search for new strategies to combat antifungal-resistant Candida strains is of paramount importance. Recently, our group reported the anti-Candida activity of a coordination compound containing copper(II) complexed with theophylline (theo) and 1,10-phenanthroline (phen), known as “CTP” – Cu(theo)2phen(H2O).5H2O. In the present work, we investigated the mechanisms of action of CTP against six medically relevant, antifungal-resistant NACs, including C. auris, C. glabrata, C. haemulonii, C. krusei, C. parapsilosis and C. tropicalis. CTP effectively inhibited the activity of mitochondrial dehydrogenases, leading to an increase in intracellular reactive oxygen species production. CTP treatment resulted in significant damage to the plasma membrane, as evidenced by the passive incorporation of propidium iodide, and DNA fragmentation as evidenced by the TUNEL assay. Scanning electron microscopy images confirmed that the fungal surface underwent substantial alterations due to CTP treatment, including the formation of invaginations that led to cavitations and lysis. These surface modifications significantly impacted the ability of Candida cells to adhere to the polystyrene surface and form a robust biofilm structure. Moreover, CTP was effective in disassembling mature biofilms formed by these NACs. CTP represents a promising avenue for the development of novel antifungals with innovative mechanisms of action against clinically relevant NACs that are resistant to antifungals commonly used in clinical settings.

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Synthesis and anticancer evaluation of copper(II)- and manganese(II)- theophylline mixed ligand complexes

Cited by 15 publications

References 62 publications

Novel Metallomacrocyclic Carboxamide Mn(II) Complexes as Efficient Catalysts for the Transfer Hydrogenation of Ketones

Novel Metallomacrocyclic Carboxamide Mn(II) Complexes as Efficient Catalysts for the Transfer Hydrogenation of Ketones

Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO2 to Synthesize α-Unsaturated Aminocarboxylic Acids

Unveiling the Antifungal Mechanisms of CTP, a New Copper(II)- Theophylline/1,10-Phenanthroline Complex, on Drug-Resistant Non-albicans Candida Species

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