[(7-chloroquinolin-4-yl)amino]acetophenones and their copper(II) derivatives: synthesis, characterization, computational studies and antimalarial activity

Parra, Yonathan; L, Felix D Andueza; Ferrer, Rosa; Colmenarez, Julia Bruno; Acosta, María Eugenia; Charris, Jaime; Rosenthal, Philip J.; Gut, Jiří

doi:10.17179/excli2019-1805

Cited by 2 publications

(2 citation statements)

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“…This demonstrates the promising outlook for the copper-chloroquine complexes to eradicate this parasite. Moreover, these two compounds showed higher antiplasmodial activity against W2 (IC 50 < 300 nM) than [(7-chloroquinolin-4-yl)amino]acetophenones and other copper complexes (IC 50 ranged from 1 to 7 µM) [ 21 ].…”

Section: Resultsmentioning

confidence: 99%

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Copper (I)-Chloroquine Complexes: Interactions with DNA and Ferriprotoporphyrin, Inhibition of β-Hematin Formation and Relation to Antimalarial Activity

et al. 2022

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A new Cu(I)-chloroquine (CQ) complex [Cu(CQ)(PPh3)2]NO3 (1) was synthesized and characterized, and its mechanism of action studied concomitant with the previously reported complex [Cu(CQ)2]Cl (2). These copper (I) coordination compounds can be considered as potential antimalarial agents because they show better inhibition of the CQ-resistant strain in in vitro studies than CQ alone. In comparison with other metal-CQ complexes, only the gold complex was similar to (1), i.e., more active than CQ against both CQ-susceptible (3D7) and CQ-resistant strains (W2). These two copper (I)-compounds also demonstrated higher antiplasmodial activity against W2 than other copper complexes reported to date. This suggests that the incorporation of the copper metal center enhanced the biological activity of CQ. To better understand their significant growth inhibition of the Plasmodium falciparum parasite, the interaction with two essential molecular targets for the survival and proliferation of the malarial parasite were studied. These were the ferriprotoporphyrin group and the DNA, both important targets for current antimalarial drugs at the asexual erythrocytic stages. Both compounds (1,2) exhibited significant interactions with these targets. In particular, interactions with the DNA were dominated by the intercalator properties of the CQ ligand but may have also been affected by the presence of copper. Overall, these compounds were better parasitic inhibitors than chloroquine diphosphate (CQDP) alone or other previously reported metal-CQ complexes such as platinum, ruthenium and gold.

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Section: Resultsmentioning

confidence: 99%

“…Recently, Parra’s group reported the synthesis and considerable antimalarial activity of two copper compounds with [(7-chloroquinolin-4-yl)amino]acetophenones. They demonstrated that complexation with Cu(II) increased the activity of free ligands against P. falciparum [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Copper (I)-Chloroquine Complexes: Interactions with DNA and Ferriprotoporphyrin, Inhibition of β-Hematin Formation and Relation to Antimalarial Activity

et al. 2022

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Insight into Recent Drug Discoveries against Trypanosomatids and Plasmodium spp Parasites: New Metal-based Compounds

Scarim

Farias

Chiba

et al. 2022

CMC

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: Scaffolds of metal-based compounds can act as pharmacophore groups in several ligands to treat various diseases, including tropical infectious diseases (TID). In this review article, we investigate the contribution of these moieties to medicinal inorganic chemistry in the last seven years against TID, including American trypanosomiasis (Chagas disease), human African trypanosomiasis (HAT, sleeping sickness), leishmania, and malaria. The most potent metal-based complexes are displayed and highlighted in figures, tables and graphics; according to their pharmacological activities (IC50 > 10µM) against Trypanosomatids and Plasmodium spp parasites. We highlight the current progresses and viewpoints of these metal-based complexes, with a specific focus on drug discovery.

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[(7-chloroquinolin-4-yl)amino]acetophenones and their copper(II) derivatives: synthesis, characterization, computational studies and antimalarial activity

Cited by 2 publications

References 37 publications

Copper (I)-Chloroquine Complexes: Interactions with DNA and Ferriprotoporphyrin, Inhibition of β-Hematin Formation and Relation to Antimalarial Activity

Copper (I)-Chloroquine Complexes: Interactions with DNA and Ferriprotoporphyrin, Inhibition of β-Hematin Formation and Relation to Antimalarial Activity

Insight into Recent Drug Discoveries against Trypanosomatids and Plasmodium spp Parasites: New Metal-based Compounds

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