Cytotoxicity of cationic NHC copper(I) complexes coordinated to 2,2'-bis-pyridyl ligands

Elie, Margaux; Mahoro, Gilbert Umuhire; Duverger, Eric; Renaud, Jean‐Luc; Daniellou, Richard; Gaillard, Sylvain

doi:10.1016/j.jorganchem.2019.04.003

Cited by 10 publications

(7 citation statements)

References 52 publications

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“…The SAR study revealed that presence of electron donor or withdrawing substituent on the pyridine ring of the cationic copper(I) complexes and unsubstituted 2,2’‐dipyridylamine have positive effect on cytotoxicity. Also, complexes having large fluorinated anions 214 e – f showed less activity due to its lipophilic nature [102] …”

Section: Medicinal Applicationsmentioning

confidence: 99%

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Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Nayak

Gaonkar

2021

ChemMedChem

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New weapons are constantly needed in the fight against cancer. The discovery of cisplatin as an anticancer drug prompted the search for new metal complexes. The successful history of cisplatin motivated chemists to develop a plethora of metal‐based molecules. Among them, metal‐N‐heterocyclic carbene (NHC) complexes have gained significant attention because of their suitable qualities for efficient drug design. The enhanced applications of coinage metal‐NHC complexes have encouraged a gradually increasing number of studies in the fields of medicinal chemistry that benefit from the fascinating chemical properties of these complexes. This review aims to present recent developments in synthetic strategies and medicinal applications of copper, silver and gold complexes supported by NHC ligands.

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Section: Medicinal Applicationsmentioning

confidence: 99%

“…Also, complexes having large fluorinated anions 214 e-f showed less activity due to its lipophilic nature. [102]…”

Section: Copperà Nhc Complexes As Anticancer Agentsmentioning

confidence: 99%

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Nayak

Gaonkar

2021

ChemMedChem

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“…Reports include Ru(II)-and Au(I)-N-heterocyclic carbenes, 15,16 Ag(I)-NHCs, as antimicrobial and anticancer agents, 17,18 and Cu(I)-NHCs possessing remarkable anticancer activity. 19 Lepidilinelike platinum(II) complexes were also synthesized and were found to be active against cancer cells. 20,21 However, metal complexes of lepidiline A or C were not investigated for their antiproliferative potential against cancer cells, and none of the plant-derived lepidilines were tested against multidrug-resistant (MDR) cancer or multipotent stem cells.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Systematic Investigation of Lepidiline A and Its Gold(I), Silver(I), and Copper(I) Complexes Using In Vitro Cancer Models and Multipotent Stem Cells

Tóth,

Szlávik,

Mandel

et al. 2024

ACS Omega

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The imidazole alkaloid lepidiline A from the root of Lepidium meyenii has a moderate to low in vitro anticancer effect. Our aim was to extend cytotoxicity investigations against a panel of cancer cells, including multidrug-resistant cancer cells, and multipotent stem cells. Lepidiline A is a N-heterocyclic carbene precursor, therefore a suitable ligand source for metal complexes. Thus, we synthesized lepidiline A and its copper(I), gold(I), and silver(I) complexes and tested them against ovarian, gastrointestinal, breast, and uterine cancer cells and bone marrow-derived and adipose-derived mesenchymal stem cells. Lepidiline A and its copper complex demonstrated moderate cytotoxicity, while silver and gold complexes exhibited significantly enhanced and consistent cytotoxicity against both cancer and stem cell lines. ABCB1 in the multidrug-resistant uterine sarcoma line conferred significant resistance against lepidiline A and the copper-lepidiline A complex, but not against the silver and gold complexes. Our results indicate that only the copper complex induced a significant and universal increase in the production of reactive oxygen species within cells. In summary, binding of metal ions to lepidiline A results in enhanced cytotoxicity with the nature of the metal ion playing a critical role in determining its properties.

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“…The emissive Cu(I)–NHC (NHC = N -heterocyclic carbene) complexes have promising features in the electrochemical cell, medicinal and organic light-emitting diode (OLED) applications. − Luminescent Cu(I)–NHC complexes have created an impact in OLED technologies since the discovery of the first luminescent Cu(I)–NHC complexes [Cu 2 (μ-Me-mbim) 2 ](PF 6 ) 2 [μ-Me-mbim = methylene linked bis(NHC)] by Matsumoto and co-workers . Subsequently, Thompson and co-workers proposed a linear donor-bridge-acceptor design strategy and developed a new class of two-coordinate CAAC-Cu-Cz [CAAC = (5 R ,6 S )-2-(2,6-diisopropylphenyl)-6-isopropyl-3,3,9-trimethyl-2-azaspiro-[4.5]decan-2-ylidene, Cz = N -carbazolyl] complexes for mononuclear Cu(I)-based thermally activated delayed fluorescence (TADF) systems for blue OLED with an external quantum efficiency (EQE) of 9%, emission at 474 nm .…”

Section: Introductionmentioning

confidence: 99%

Organo Chalcogenone-Triggered Luminescent Copper(I) Clusters for Light Emitting Applications

Veerapathiran,

Muduli,

Rawat

et al. 2024

Inorg. Chem.

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A novel organo sulfur and selenium-controlled emission behavior in discrete copper(I) clusters has been demonstrated for the first time. The pentanuclear [Cu 5 Br 5 (L 1 ) 2 ] (1), trinuclear [Cu 3 Br 3 (L 2 ) 2 ] (2), dinuclear [Cu 2 I 2 (L 1 ) 2 ] (3), and tetranuclear [Cu 4 I 4 (L 2 ) 2 CH 3 CN] (4) copper(I) discrete clusters have been synthesized from the reaction between L 1chelating ligands and corresponding copper(I) halide salts. These new clusters have been characterized by FT-IR, UV−visible, thermogravimetric analysis, and fluorescence spectroscopy techniques. Single-crystal X-ray diffraction studies reveal that 1−4 consists of abundant d 10 − d 10 interactions. The structural and bonding features of clusters have been investigated using density functional theory calculations. Notably, the L 2 -ligated 2 and 4 are poorly emissive, while L 1ligated 1 and 3 showed strong emission in the orange and green regions, respectively. The time-dependent density functional theory natural transition orbital calculations of 1 and 3 reveal the nature of the transitions contributed by 3 MLCT/ 3 LLCT/ 3 ILCT. Photoluminescence quantum yields of 1 and 3 are 19 and 11%, with average lifetimes of 21.55 and 6.57 μs, respectively. 1 and 3 were coated on prototype LED bulbs for light-emitting performance.

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Cytotoxicity of cationic NHC copper(I) complexes coordinated to 2,2'-bis-pyridyl ligands

Cited by 10 publications

References 52 publications

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Coinage Metal N‐Heterocyclic Carbene Complexes: Recent Synthetic Strategies and Medicinal Applications

Synthesis and Systematic Investigation of Lepidiline A and Its Gold(I), Silver(I), and Copper(I) Complexes Using In Vitro Cancer Models and Multipotent Stem Cells

Organo Chalcogenone-Triggered Luminescent Copper(I) Clusters for Light Emitting Applications

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