Oxidative dimerisation of 2-aminophenol by a copper(II) complex: Synthesis, non-covalent interactions and bio-mimics of phenoxazinone synthase activity

Mukherjee, Subham; Roy, Suvojit; Mukherjee, Shirshendu; Biswas, Bhaskar

doi:10.1016/j.molstruc.2020.128348

Cited by 11 publications

(6 citation statements)

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“…All the redox events are found to be in good accordance with the reported literature of Cu( ii ) complexes. 61–63 Likewise, in complex 2 , one irreversible peak at −1.112 V and two quasi reversible redox events at −1.376 V and −1.70 V were observed for ligand ( L )-based redox events (Fig. S7, ESI†).…”

Section: Resultsmentioning

confidence: 99%

Triazine-based mononuclear copper(ii) cis-dichloro and dibromo complexes as functional biomimetic model systems for phenoxazinone synthase and catecholase activities

Roy,

Muley,

Mathur

et al. 2024

New J. Chem.

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Section: Resultsmentioning

confidence: 99%

Triazine-based mononuclear copper(ii) cis-dichloro and dibromo complexes as functional biomimetic model systems for phenoxazinone synthase and catecholase activities

Roy,

Muley,

Mathur

et al. 2024

New J. Chem.

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“…The proposed formulae of ( 1 )–( 4 ) are supported by elemental analyses. The crystal structure of the mononuclear copper(II) complex ( 1 ) has been previously reported with one chelated water molecule and two phen ligands and having a distorted trigonal bipyramid geometry about the copper atom [ 32 ]. The structure of the dicopper(II) 4,4′-bipy-bridged complex ( 3 ) is reported herein (Fig.…”

Section: Resultsmentioning

confidence: 99%

Dinuclear and mononuclear metal(II) polypyridyl complexes against drug-sensitive and drug-resistant Plasmodium falciparum and their mode of action

Lai

Maah

Tan

et al. 2022

Malar J

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Background Malaria remains one of the most virulent and deadliest parasitic disease in the world, particularly in Africa and Southeast Asia. Widespread occurrence of artemisinin-resistant Plasmodium falciparum strains from the Greater Mekong Subregion is alarming. This hinders the national economies, as well as being a major drawback in the effective control and elimination of malaria worldwide. Clearly, an effective anti-malarial drug is urgently needed. Methods The dinuclear and mononuclear copper(II) and zinc(II) complexes were synthesized in ethanolic solution and characterized by various physical measurements (FTIR, CHN elemental analysis, solubility, ESI-MS, UV-Visible, conductivity and magnetic moment, and NMR). X-ray crystal structure of the dicopper(II) complex was determined. The in vitro haemolytic activities of these metal complexes were evaluated spectroscopically on B+ blood while the anti-malarial potency was performed in vitro on blood stage drug-sensitive Plasmodium falciparum 3D7 (Pf3D7) and artemisinin-resistant Plasmodium falciparum IPC5202 (Pf5202) with fluorescence dye. Mode of action of metal complexes were conducted to determine the formation of reactive oxygen species using PNDA and DCFH-DA dyes, JC-1 depolarization of mitochondrial membrane potential, malarial 20S proteasome inhibition with parasite lysate, and morphological studies using Giemsa and Hoechst stains. Results Copper(II) complexes showed anti-malarial potency against both Pf3D7 and Pf5202 in sub-micromolar to micromolar range. The zinc(II) complexes were effective against Pf3D7 with excellent therapeutic index but encountered total resistance against Pf5202. Among the four, the dinuclear copper(II) complex was the most potent against both strains. The zinc(II) complexes caused no haemolysis of RBC while copper(II) complexes induced increased haemolysis with increasing concentration. Further mechanistic studies of both copper(II) complexes on both Pf3D7 and Pf5202 strains showed induction of ROS, 20S malarial proteasome inhibition, loss of mitochondrial membrane potential and morphological features indicative of apoptosis. Conclusion The dinuclear [Cu(phen)-4,4′-bipy-Cu(phen)](NO3)4 is highly potent and can overcome the total drug-resistance of Pf5202 towards chloroquine and artemisinin. The other three copper(II) and zinc(II) complexes were only effective towards the drug-sensitive Pf3D7, with the latter causing no haemolysis of RBC. Their mode of action involves multiple targets. Graphical Abstract

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“…The literature survey indicates the availability of many studies on copper complexes that functionally mimic both COX and PHS individually 8–26 . In the same context, articles dealing with copper complexes that mimic the biocatalytic activity of both enzymes are relatively few 27–33 .…”

Section: Introductionmentioning

confidence: 99%

“…1 The literature survey indicates the availability of many studies on copper complexes that functionally mimic both COX and PHS individually. [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] In the same context, articles dealing with copper complexes that mimic the biocatalytic activity of both enzymes are relatively few. [27][28][29][30][31][32][33] Therefore, further studies on the synthesis of Cu (II) chelates that mimic the activity of the two enzymes involved are a good addition to the field of biomimetic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Copper (II) complexes based on the mixed ligand system: Study of synthesis, characterization, and stopped‐flow kinetics of copper oxidase‐mimicking catalytic activity

Abo El‐Kheir,

Shaban,

Ibrahim

et al. 2024

Applied Organom Chemis

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Two copper (II) complexes based on the mixed ligand system were synthesized and structurally characterized. The molecular formulae for complex (1), [Cu2L1L′] and complex (2), [CuL2L′] were determined based on analytical data, molar conductance, and thermal analysis results. The optimized structures of complexes (1) and (2) were determined by magnetic and spectroscopic measurements (FTIR, UV–Vis, and ESR) and confirmed by processing powder X‐ray diffraction data by Expo 2014 software. The geometry index (τ5), determined by ESR spectra and structural analysis based on powder X‐ray, demonstrates the square pyramidal geometry of the Cu (II) center of [Cu2L1L′] and [CuL2L′]. Cyclic voltammetry measurements were performed to elucidate the relationship between the redox properties of (1) and (2) and their oxidase‐mimicking catalytic activity. Catalytic aerobic oxidation of the polyphenols 3,5‐di‐tert‐butylcatechol (3,5‐DTBCH2), 4‐nitrocatechol, and 2‐aminophenol (2‐APH3) was studied by stopped‐flow technique. Promising catechol oxidase (COX) and phenoxazinone synthase (PHS) mimetic activity have been demonstrated for (1) and (2). Electrochemical data were used to determine the free energy (ΔG°) or driving force (−λ), and their correlation with the oxidase mimetic activity of(1) and (2) was examined. Several experimental procedures have been performed that have helped describe the catalytic mechanisms of the catalytic reactions taking place.

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Oxidative dimerisation of 2-aminophenol by a copper(II) complex: Synthesis, non-covalent interactions and bio-mimics of phenoxazinone synthase activity

Cited by 11 publications

References 50 publications

Triazine-based mononuclear copper(ii) cis-dichloro and dibromo complexes as functional biomimetic model systems for phenoxazinone synthase and catecholase activities

Triazine-based mononuclear copper(ii) cis-dichloro and dibromo complexes as functional biomimetic model systems for phenoxazinone synthase and catecholase activities

Dinuclear and mononuclear metal(II) polypyridyl complexes against drug-sensitive and drug-resistant Plasmodium falciparum and their mode of action

Copper (II) complexes based on the mixed ligand system: Study of synthesis, characterization, and stopped‐flow kinetics of copper oxidase‐mimicking catalytic activity

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