Anticancer, antimicrobial and antiparasitical activities of copper(I) complexes based on<i>N</i>-heterocyclic carbene (NHC) ligands bearing aryl substituents

Touj, Nedra; Nasr, Ibrahim Al; Koko, Waleed S.; Khan, Tariq A.; Özdemır, İsmaıl; Yaşar, Sedat; Mansour, Lamjed; Alresheedi, Faisal; Hamdi, Naceur

doi:10.1080/00958972.2020.1836359

Cited by 25 publications

(12 citation statements)

References 68 publications

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“…[ 5,6 ] In recent years, metal‐N‐heterocyclic carbene (NHC) complexes have shown promise in biomedical applications, including as antimicrobial, anticancer, and antitumor (palladium‐, copper‐, silver‐, gold‐, ruthenium‐, rhodium‐, and platinum‐NHC) agents. [ 7–36 ] The efficacy of a silver‐based drug appears to be linked to its bioavailability [ 13,37 ] which is affected by, for example, its solubility and the presence of biological ligands and halides. The release rate of silver from a prodrug is linked to the ancillary ligand, and as NHCs are strong σ donors, silver‐NHCs can have a slow silver release rate.…”

Section: Introductionmentioning

confidence: 99%

Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Türker

Üstün

Günal

et al. 2022

Archiv der Pharmazie

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The reaction of N-substituted benzimidazole with 4-bromobutyronitrile gives the corresponding benzimidazolium salts as N-heterocyclic carbene (NHC) precursors. Silver(I) carbene complexes are synthesized by the reaction of the corresponding benzimidazolium salts with Ag 2 O in dichloromethane. These new NHC precursors and Ag-NHC complexes were characterized by spectroscopy techniques and also screened for their antibacterial activities against the standard bacterial strains Escherichia coli, Pseudomonas aeruginosa, Acinetobacter baumannii, Klebsiella pneumoniae, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Enterococcus faecalis, and the standard fungal strains Candida albicans and Candida glabrata, and promising results were achieved. The compounds were also analyzed by density functional theory (DFT)/time-dependent DFT and docking methods.

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Section: Introductionmentioning

confidence: 99%

Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Türker

Üstün

Günal

et al. 2022

Archiv der Pharmazie

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“…The high lipophilicity and charge of compound ( 4 ) may be considered critical properties that caused the higher cytotoxicity to the host cell. Comparing this work with the results of Touj and colleagues, novel designs should consider a balance between NHC steric hindrance and lipophilicity [14,61,62,68] …”

Section: Resultsmentioning

confidence: 54%

“…The selectivity indexes showed that these complexes have an SI>1, higher than that found by Touj and colleagues for a series of the type [Cu(I)(BzIM)X], where BzIM represents R‐2,3‐dihydro‐1H‐benzoimidazol‐2‐yl, and X is chloride or bromide against promastigotes of L. major and the viability against Vero cells [14] …”

Section: Resultsmentioning

confidence: 59%

“…Besides, NHCs exhibit low toxicity and a high possibility of structural variations that allow an adjustment of several chemical and drug‐like properties, such as lipophilicity, water stability, and reactivity. Cu(I)NHC were investigated as anticancer agents, antitoxoplasmal, leishmanicidal, and antimicrobial activities [14,15] . Concerning the leishmanicidal activities, a series of neutral Cu(I) benzimidazole‐R‐ylidene compounds showed selectivity indexes around 2.…”

Section: Introductionmentioning

confidence: 99%

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Antileishmanial and Anti‐Chikungunya Activity of Cu(I)‐N‐Heterocyclic Carbenes

et al. 2022

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Neglected tropical diseases such as Leishmaniasis and Chikungunya fever are worldwide public health challenges mainly affecting tropical and subtropical countries. One cationic [Cu-(I)(NHC) 2 ] + (4) and two neutral [Cu(I)(NHC)Cl] complexes, where NHC = 1,3-bis(mesityl)imidazole-2-ylidene (IMes) (5) or 1,3-bis-(2,6-diisopropylphenyl)imidazole-2-ylidene (IPr) (6), had their in vitro activity evaluated towards Leishmania amazonensis and Chikungunya virus (CHIKV). The compound (6) inhibited 95 % of L. amazonensis infection in RAW macrophages at 10 μM and 90 % of the CHIKV replication at 2 μM in BHK-21 cells. Otherwise, the other compounds showed higher cytotoxicity in BHK-21 and RAW or lower antiparasitic or antiviral activities.The best activity of compound 6 can be explained by slower ligand exchange with solvent molecules measured by 1 H NMR technique and the best hydrophilic/lipophilic balance (log P = À 0.684 � 0.055) in the series determined by shake flask method. Antioxidant activity measured by reduction of DPPH revealed a moderate redox ability of all complexes. The binding constant of ( 6) with bovine serum albumin (BSA) represents the weakest in the series (10 3 ). The chemical and in vitro evaluation reported here represent a novel application and chemical insights for the design of [Cu(I)(NHC)L] metallodrugs for these infectious diseases.

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“…While working on the introduction to our personal article, we found that in 2020 alone, more than 50 papers were published, which describe the results of a study of the antimicrobial activity of copper complexes. During the preparation of the manuscript for submission a number of works [59][60][61][62][63][64][65][66][67][68][69] were published that were not included in the above analysis.…”

Section: Discussionmentioning

confidence: 99%

Recent Studies on the Antimicrobial Activity of Copper Complexes

Zalevskaya

Gur’eva

2021

Russ J Coord Chem

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The analysis of publications in 2020, devoted to the synthesis of copper(II) complexes and the study of their antimicrobial properties, indicates that this area of medicinal chemistry is promising. Organic compounds of various classes were studied as starting ligands. First of all, these are N-donor imines, amines, heterocyclic compounds, as well as N,O-donor ligands and sulfur-containing ligands. In most works, the fact of a higher biological activity of the metal complex in comparison with the corresponding ligand was established. Evaluating the influence of the nature of the metal on the antimicrobial activity of the metal complex, the authors most often come to the conclusion that it is copper(II) complexes that are the most effective inhibitors of the growth of pathogenic bacteria. The scale of the studies presented indicates a high interest in this group of metal complexes, and the results indicate good prospects for using copper complexes as antimicrobial drugs.

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Anticancer, antimicrobial and antiparasitical activities of copper(I) complexes based onN-heterocyclic carbene (NHC) ligands bearing aryl substituents

Cited by 25 publications

References 68 publications

Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis

Antileishmanial and Anti‐Chikungunya Activity of Cu(I)‐N‐Heterocyclic Carbenes

Recent Studies on the Antimicrobial Activity of Copper Complexes

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